Organic polarography - ACS Publications

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Organic Polarography Donald J. Pietrzyk Department of Chemistry, University of Iowa, Iowa City, Iowa 52242

This review surveys articles described in Chemical A b stracts, Analytical Abstracts, Electroanalytical Abstracts, Chemical Titles, and readily available journals ending November 30, 1973. This period has seen a continued growth in the use of polarography and related electrochemical techniques to follow chemical reactions and to supplement other physical and spectral measurements for purposes of characterization. Interest in applications toward biochemical and pharmaceutical problems has also increased. There also appears to be renewed interest in utilizing polarographic and related electrochemical data to predict and follow organoelectrochemical synthesis. In this review the symbols cv, dc, ac, and op are used to identify cyclic voltammetry, direct current polarography, alternating current polarography, and oscillographic polarography, respectively. Also, no attempt was made to list all organic polarographic references. GENERAL REVIEWS Several general type reference books have been published. These deal with adsorption (222, 348), reactions in nonaqueous solvents ( 7 3 0 , electrode kinetics (2080), use of computers (744), role of acidity, free radicals, and of the double layer (2216), a general survey (488),and with biological compounds ( 2 227). Papers presented a t meetings have been published (153, 2195). Considerable interest in electrochemical synthesis and the use of polarography to predict the conditions or to follow the progress of the electrolysis has appeared. Several excellent books in this area have recently become available (53, 350, 2203). General polarographic reviews including organic polarography were compiled (100, 287, 334, 2260). Other reviews survey pulse polarography (551),op (244),and electrode processes (452). The stereochemistry of electrochemical reductions (351), role of free radicals (558), feasibility of using polarography to study monomer reactivity and polymer reaction kinetics (95), redox potentials for aromatic compounds (960), and kinetics and mechanisms of electrode processes leading to polymerization (230) have been reviewed. Surveys covering electrochemistry of P, As, Sb, S, and C onium salts and quaternary N salts (585), monoand dihalogen compounds ( E O ) , the determination of carbonyls after condensation with o-phenylenediamine (2245), the ECE mechanism and the effect of pH (2233), and cv data for oxidation of formic acid a t noble electrodes (266) were made. The EE and ECE mechanisms were computer-calculated and the calculations tested by the oxidation of 5,10-dihydro-5,10-dimethylphenazine and by the reduction of methylviologen and anthraquinone in MeCN (409). A survey of cathode ray and ac data were reported for 20 different nitro compounds (explosives) (447). Prediction of reduction potentials by SCF and HMO methods for fused aromatic hydrocarbons (358) and correlations between E1 2 for unsaturated hydrocarbons and energies of lowest vacant MO (734) were reviewed. Organic oxidation potentials and ionization potentials for 68 different organic compounds were correlated and used for predictions (765). Correlations between Ell2 for pDCeH4A, where D and A are electron donor and acceptor groups, and electronic spectra transitions were possible ( 704). The polarographic determination of organic pollutants 52R

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in water (505)and pesticides (1054)have been reviewed. The applications of polarography in medicine (IO%), for proteins (4671, for kinetic studies of biological redox reactions (296),for biologically active compounds (2036), and for pyridine and pyridine coenzyme derivatives (1073) were reviewed. Analyses of drugs (456) and biological compounds (803) were surveyed. Reviews covering op data for biological compounds (355) and for alkaloids, antibiotics, and drugs (549) are available. Polarographic instruments and procedures for biochemical applications were reviewed (436). I n uiuo measurements and identification of major electro active species ( a t Pt) in rat blood serum were described (907). Integration procedures in ac (335), an instrument for first drop polarography [tested with glycol aldehyde (582)], a cell for simultaneously recording (ESR) and producing radical species (cv) (tested with quinones, aromatics, and nitro compound) (377),and an ac instrument for performing kinetic studies at 4 frequencies simultaneously (tested with cyclooctatetraene) (480) have been reviewed. Low temperature techniques (>- 130 "C) and their applications were reviewed in detail and tested with several systems (2136, 2137). A general survey of the effect of nonaqueous solvents on E1,2 was made (600). The properties and purification of DMF (550) and DMSO (595) for voltammetric studies were reviewed. The use of carbon graphite electrodes 29), Hg, Pt, and C electrodes (310), and rotating ring-dis electrode (785) were reviewed. Surveys on the measurement of sorption of H and organic compounds on Pt (2022) and the use of CHzClz solvent with Pt, Ag, and DME (228) were made. The influence of the composition of C paste electrodes in the presence of surfactants was studied by cv (802) while methods of preparation, resurfacing methods, surface and static charge, adsorption, acidity, potential range, and scanning procedure and their effects on the use of glassy carbon and pyrolytic graphite electrodes in cv studies (847) were reviewed. Identification and study of the surfaces of different kinds of C and coal were described (255, 300,375). Several different surfactants were investigated as maxima suppressors (726), and a new electrochemisorption effect was suggested and tested with several systems (708). Streaming effects in polarographic maxima were described (69).

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QUINONES-HYDROQUINONES The effect of proton donors and the study of a prewave for reduction of methyl-p-benzoquinone was reported (1061, 2062). A cv study was reported for solid quinones (10) and for the hydroxylation of quinones, hydroquinones, phenols, naphthols, and hydroxyquinolines (848). Reduction data for o-benzoquinone were described (605). Oxidation of hydroquinone in MeCN a t a rotating-disk electrode (288) and for hydroquinone and phenidone (522) was reported. A one-electron intermediate was suggested in a cv study of hydroquinone in the presence of proton donors (853).A cv study of hydroquinone in MeCN-H2O mixtures (664) and for its phosphate and sulfate esters a t the carbon paste electrode (746)was carried out. The reaction between hydroquinone and oxygen (31) and the kinetics for the photochemical reaction of chlorani1 (1292) were followed by polarography. The effect of

Donald J. Pietrzyk. professor of chemistry at the University of Iowa. received his BS degree in chemistry from Wayne State University in 1956 and his PhD in analytical chemistry at Iowa State University in 1960 H e joined the chemistry staff at Iowa in 1961 after a one-year postdoctoral appointment at MIT His chief professional interests in analytical chemistry are in separations, ion exchange and other chromatographic methods, organic analysis, and nonaqueous acid-base chemistry

lated to substituent constants. Correlations between Hammett-Taft values and chemical reaction properties with E112 oxidation values were described for 0- and p substituted thiobisphenols (40) and substituted bisphenols (41). Oxidation data for 22 phenol derivatives were correlated to ionization Dotentials and x electron charges a t oxygen (707). Amidol (2,4-diaminophenol) (255, 911) and phenol in aqueous solution (1169) were determined polarographically. A special instrument was described for the electrolytic determination of phenols on filter paper after separation

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(780).

Dichloromethane-THF mixture was used in a cv study of o-bromo- and o-methylanisole (71). Hydroxylation reactions encountered in anodic oxidation of phenolic compounds (849), and anodic dimethoxylation reactions for the alkyl group on reduction of neopentyl hydroquinones methyoxyphenols at carbon paste electrode (877) were was noted (688). Hydroquinone and metol (N-methyl-4studied by cv techniques. A dc and cv study of tetranisylamidophenol) in mixtures were determined polarographi2,3,4,5-pyrrole was described (687). Oxidation data for p cally (741) . dimethoxybenzene and 9-phenylanthracene were reported Half-wave potentials for 24 quinones were correlated to in an electrochemical study of their oxidation in the pres13C-NMR chemical shifts (84). Correlations between Ell2 ence of CN- as a substituting agent (962). Oxidation data and substitution constants were also found for methyl for all methoxy isomers of benzene were correlated to substituted quinones and hydroquinones containing a pcharge transfer absorDtion bands for these comDounds tolythio substituent (139). withyCNE (956). Polarographic data were reported for 1,2-naphthoquiEthyleneglycol in the atmosphere (478) and triethylene none-1-diazide and 1,2-naphthoquinone-l-diazide-4-sul- dvcol dimethacwlate in polyester varnish (767) were defonic acid (344), for alkyl substituted naphthoquinones &mined by polarography. Tocopherol content of vegeta(758) and for naphthoquinone, juglone, and other substible oil was analyzed by linear sweep voltammetry (710) tuted quinones (608). Solvation effects on the reduction of while an ac technique was used to determine the degree of 1,2- and 1,4-naphthoquinones were related through an ethoxylation of alkyl phenol glycol ether (625). equation (628), while the reaction between 1,4-naphthaOxidation data for benzyl alcohol in MeCN (142) and quinone and superoxide ion was followed polarographicafor p-methoxy-benzyl alcohol (141) were reported. A cv lly (324). Relative electron affinities for acceptors for quitechnique was used to investigate the system methanolnone-aromatic hydrocarbon charge transfer complexes electrolyte-electrode (513), 2-methoxyethanol (940), and were evaluated from Ell2 data for 2,3-dichloro- and 2,3for a series of alkylcyclohexylphenols as a function of pH dicyano-1,4-naphthoquinonederivatives (189). (990). Several p-substituted deoxybenzoins were reduced Polarpgraphic data were reported for anthraquinone and polarographically in HZO-EtOH media (928). several polyaromatics (474) and for anthraquinone and Anodic oxidation data were reported for I different alibenzanthrone in DMF (900). The effect of organic acids phatic alcohols in three different solvents (1050) and for and bases (572), acid-base properties of solvent (571), and primary alcohols and the influence of adsorption (825). of supporting electrolytes and solvents (470) on the poThe effect of supporting electrolyte on the tensammetric larographic characteristics of anthraquinone were dewave for tert-pentylalcohol (964), the adsorption of isoamscribed. The acidity of organic acids was determined from yl alcohol and polyethylene glycol on the DME (256), and their effect on anthraquinone reduction (569). Heterocythe adsorption and effect of poly(vinylalcoho1) on polaroclic derivatives of anthraquinone were studied in DMF graphic maxima (957) was described. Polarographic maxi(678). ma in borneol (349) and adamantanol-1 and -2 (817) soluCorrelations between Ell2 and visible absorption spections were studied. tra of anthraquinone radical anions were reported (353). Polarographic data were described for polyethylene Anthraquinone and 2-chloro- and 2-amino derivatives oxide derivatives of fatty alcohols, alkylphenols, and fatty were determined polarographically (901). amines (466). Production of a 1,2-dihydroxyethyl radical Reduction potentials were reported for seven 3-substiwas followed by polarography in pulse irradiation of NzO tuted phenanthrenequinones as a function of pH (104). saturated ethylene glycol solutions (59). Correlations between E112 and Hammett u-constants for 23 acenequinones and heteroacenequinones were described (784). ALDEHYDES Phenolsulfophthalein reduction was studied as a funcPolarographic data were reported for a-cyanoisobutanal tion of pH (1148).A series of sulfonephthaleins were used and isobutanal (566), 3-methyl crotonaldehyde (761, 764), to evaluate cv theory for disproportionation reactions that and phthalaldehyde (857). Reduction of glutaric and adipare initiated electrolytically (635, 636) and to test a comic dialdehyde (262) and phthalaldehyde by dc and cv puterized data acquisition system in a cv study (167). techniques (874) was studied as a function of pH. Fluorescein was investigated as a function of ionic The reduction mechanism for glycol aldehyde in alkastrength, type of buffer, and buffer capacity (1153) while line solution was described (580). An ECE mechanism pH was the variable in the study of eosine and erythrosine was suggested for the reduction of acenaphthenon alde(508). hyde and acenaphthylene (365). The reduction of 4,5-dibromo-fluorescein (57, 802), diAnodic oxidation of aromatic aldehydes was reported for chloro-, dibromo-, and diiodofluorescein (506) and eosine alkaline solutions and these data were related to rate con(56) were studied as a function of pH. Alizarine S was exstants for chromic acid oxidation (732). Correlations were amined by dc and ac polarography (83). also found for E l l z data with Hammett u values for w-substituted vinyl aldehydes (632) and for substituted comALCOHOLS, GLYCOLS, A N D PHENOLS pounds of the type RR’P(O)CH=CHMeCHO (146). A detailed electrochemical study of the oxidation of Aromatic aldehydes and ketones (748) and aldehydes in 2,6-xylenol at Pt (514) and for 2,6-di-tert-butyl-p-cresol industrial waste waters (305) were determined by an op technique. A procedure for the determination of 2,2-di(856) in MeCN was described. Half-wave potentials for phenols and anilines on graphite were compared to data methyl-/3-hydroxypropionaldehyde and isobutraldehyde on Pt (1163). was reported (1084). Formaldehyde in strong acid soluEffect of solvent composition on E l , z and correlation to tions was determined polarographically (299). efficiency of substituted phenols to act as antioxidants The reduction of HzCO was studied at the DME and a was described (573). Oxidation data for twenty-eight 2-, rotating amalgamated Cu disk electrode (203). Formalde2,4-, and 2,4,6-substituted phenols (391) and reduction hyde was used as a model system to test concurrent DTA data for 11 substituted phenoxy radicals (503) were correand cv measurements (400). A N A L Y T I C A L C H E M I S T R Y , VOL. 46, N O . 5 , A P R I L 1974

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The mechanism for the reduction of chalcones of 2- and 4-acetylpyridines was reported (750).The effect of substituents on the reduction of chalcones of the type p RC&(CH=CH),COC6H~ (1194) and a correlation between El,2 and substituent constants for trans chalcones (44) was described. Pyridyl analogs of chalcone were studied as a function of pH and the data were correlated to Hammett-Taft constants (152). Half-wave potentials for C6H&H2COC,jH&-p derivatives (1002) and 14 derivatives of trans-3-benzylidene KETONES indol-2(3H)-ones (188) were correlated to Hammett u constants. Correlations between El12 values for several carPolarographic data for cyclohexanone in acid (511), a t 20 and 70 C" (724), and for its 6-amino derivative (1142) bonyl compounds and frequencies for a carbonyl stretch and u+ constants were found (510). Energies for the lowwere reported. Mesityl oxide was studied as a function of est molecular orbital were related to Ell2 values for 2pH (1201) and determined polarographically in the presmethylene-1-cycloalkanones(597). ence of diacetone (336). Carbonyl compounds were used to test an equation Reduction data were discussed for 1-benzoyl-2-aryl cywhich relates E1/2 to dipole moment of the group being clopropanes (259),for D( - )phenylacetyl carbinol (315),for reduced and polarity of the solvent used (385). CorrelaC6H5COC02H (340), a series of aliphatic ketones (1018), tions between n-A* triplet energies and E112 data were reand for benzoyl cyanide in buffered mixed solutions (1183). Apoverbenone (6,6-dimethyl-3-norpinen-2-one) ported for aromatic ketones and aldehydes (696) and for acetophenones (697). Energies for the lowest K-A* triplet (406), 7 different phenyl quinolyl ketones (504), and 10state and El/* values for cyclic unsaturated ketones in methylene-9-anthrone (855) were studied by dc and cv MeCN were correlated (693). techniques. Reduction data were reported for several a,@-unsatuThe effect of cis-trans geometry was noted in a dc and rated carbonyl compounds in aqueous and nonaqueous socv study of dibenzoyl-styrene, -ethylene, -stilbene, -cylutions (465, 473, 476), a-ethylene-phenone derivatives clopropane, -phenylcyclopropane, and -diphenylcyclopro(752), and for C&(CH=CH), CO(CH=CH),CsH5 depane (1188). Polarographic data were reported for transrivatives (860). a,@-Acetylenicketones derived from ben1-aryl-2-benzoyl cyclopropane and substituted derivatives zoylacetylene (238) and a,w-diphenylpolyene ketones (861) (1193) and for I, were studied as a function of pH. Polarographic data were reported for CeH5CO0 CHC1COC6H5 and C&COCC1MeCOC6H5 (38), 1,2,3,4tetraoxo-1,2,3,4-tetrahydronaphthalene(405), a-diones in DMF (552, 553), and for bis(carbodicyano)cyclobutene dione dianion and radical anion (703). 5- and 3-Formyl-2acetylthiophene were studied as a function of pH (718). Reduction data for 4,4'-diacetyldiphenylethane were obI I1 tained in electrolysis studies (668). Intermediates in the amino acid-ninhydrin reaction where Z = -CH2S-, -OCH2-, -CH2; (446). Oxidation were detected by a cv technique (660).The effect of elecdata for dimercaDtothioDvrone derivatives.. 11.. were studtrolyte was noted in a study of fluorenone and indaneied a t a graphite electrode 135). trione-1,2,3 (667). Mechanisms for the reduction of XOCH=CHCOR, Polarographic data were reported for 2-amino-1-indanwhere R = Me. and X = Me, OMe, NH2, C1, OH, or X = one and 2-amino-1-indanon-3-01 as a function of pH (1143) H and R = alkyl groups ( 3 ) , the'reduction of aromatic and for several 2-alkyl and -aryl substituted 1,3-indancarbonyls in ethanolic alkaline media (790),and for benzil diones (1119). Reduction of 2-arylthio- and 2-aryloxy-1,3(ECE) (775) were discussed in detail. Polarographic data indandiones were compared to the 2-aryl derivative (872). for N-n-butylpiperidone-4 and its bis(pyridy1methine) de2-Acylindandiones used as rodenticides were determined rivatives (197) and for p-substituted deoxybenzoin derivapolarographically (540). tives (928)were listed. Carbonyl groups in polycaproamide (1046) and l-bromoand l,l-dibromo-3-phthalimido-2-propanone (582) were CARBOXYLIC ACIDS, ESTERS, AMIDES, AND determined polarographically. An op technique was used NITRILES to follow the acid hydrolysis of ethyl glucose cycloacetoaPolarographic data for mono- and di-chloro maleic and cetate (909), while the oxidation of 4-acetylacenaphthene fumaric acid (28), for EDTA and EDTA type derivatives was followed polarographically (646). Polarographic data (876),for picolylaminodiacetic acid (l028),and for trimelfor isatin and derivatives (307) and their hydrolysis (613) litic acid and its determination (649) were reported as a were determined polarographically. function of pH. Anodic polarography was used to generate The effect of proton donors on the reduction of aromatic radicals from triphenylacetic acid in MeCN for ESR studcarbonyls containing a hydroxy group (570) and on acetoies (606). Half-wave potentials for several aromatic acids phenone and other carbonyls (555) was discussed. Reducare listed in electrolysis studies leading to the correspondtion data were reported for benzalacetophenone in DMFing aldehyde (1173). MeOH (468) and for acetophenone in the presence and The anodic waves for formic acid at P t in H2S04 soluabsence of COz (469). Electrolysis of acetophenone, acetion (981) and detection of formate ion in presence of CO tone, and 2-butanone in aqueous NaOH was-followed poin alkaline solutions by cv techniques (428) was described. larograpliically (1016). Oxidation of acetophenone at Cu Formic acid oxidation a t Pt electrodes was studied in deelectrodes was investigated (109). The influence of a subtail in the presence of catalyst poisons MeCN and Hg stituents on acetophenone in hydrodimerization studies (27). Polarographic techniques were used to study the ef(19) and of adsorption of w-diazoacetophenone on polarofect of electrolytes on proton transfer during recombinagraphic activity (51)was described. tion with fumarate monoanion (905). Polarographic data were reported for benzophenone in Procedures were reported for the polarographic determipyridine (753) and for benzophenone and fluorenone in nation of impurities in terephthalic acid (76), glyoxalic DMF and EtOH (547). Benzophenone cv data in liquid acid in glyoxal (154), fulvic acids (1007), tetrachloromuNH3 were compared to data for alcoholic solution (242).A conic acid isomers ( l o l l ) , and for aliphatic dicarboxylic procedure was reported for the determination of benzophenone derivatives in glass-fiber reinforced plastics (97). acids (1069).Other procedures were outlined for the analysis of anhydride and acid impurities in monomers (826), The effect of supporting electrolyte on kinetic currents for maleic and fumaric acids in polyester type hydrolysates 3,3',4,4'-benzophenonetetracarboxylic acid was studied (824), trimellitic acid in mixtures with its isomers (1118), (634).Correlations between ac data for substituted benzomaleic anhydride in the production of succinimide addiphenones and corresponding thio-ketones with n-A* triplet tives (64.8) and for nitrilotriacetic acid in the presence of energies and substituent constants were described (695). The appearance of H2CO in the dissociation of several carbamate derivatives (1024) and the disproportionation of methylglyoxal into lactic acid (317) was followed by polarography. A cv technique was used to determine the kinetics for the dimerization of phthalic aldehyde and phthalic anhydride radical anions with alkali metal ions in DMF (666). The rate of hydration and polarographic data for p-OHCC&4CHO, and p-CeH4-Ac2 was determined by an op technique (554).

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metal ions (245). Polarographic data were reported for 2,6-, 2,7-, and 1,5-naphthalenedicarboxylicacid and the technique was used for determination of the 2,6-compound (356). Intramolecular deprotonation during electro-oxidation of o-, m-, and p-salicylic acid was followed a t the graphite electrode (1038). The interaction between salicylic acid and boric acid was investigated by dc and cv techniques (292,458). Polarographic data were reported for aliphatic carboxylic esters (720),methyl esters of a- and P-thiophenecarboxylic acids (757), a&-unsaturated esters in MeCN in electrolysis studies (592), and for esters of a,p-unsaturated acids with functional groups in the alkoxy1 radical (787). Esters of the type p-MeO2CC6H4XCsH4C02Me-p where X = S, 0, Se, S02, and CH2CH2 were also studied (1027). Two waves as a function of pH were reported for the reduction of dimethyl esters of cis-tetrachloromuconic acid (1012). A detailed electrochemical study of the oxidation of phenylbenzoates was described (46). A 2-step reduction was observed for 3,3’-methylenebis(4-hydroxycoumarin) (dicoumarol) in DMF (500). The Polarographic method was used to determine esters and cellulose type plastics (99), coumarins (2162),and to follow the copolymerization of methyl methacrylate with methacrylic acid (102). The kinetics of polymerization of propargyl acrylate and itaconates was studied polarographically (923). Effect of substituents on the reduction of 3-aryl methylene phthalides of the type IIIa were considered (78).

I11 Z =O(a), N(b)

Polarographic data were reported for esters and amides of the type Ar(C2)C02CH2(C’2)Ar’ and Ar(C2)CONHCH2(C2’)Ar’ where C2 and C2’ are CLS and trans ene and yne units (833). A detailed electrochemical study of the electrohydrodimerization reaction of dimethyl fumarate in the presence of cinnamonitrile and acrylonitrile in DMF was described (916). Mechanistic studies were reported for the reduction of several N-substituted phthalimides in DMF (309), for 1,2-dicarboximides (49, and for N-benzoyl and N-phenyl diimides (665). The anodic oxidation of DMF was studied in MeOH and HOAc in the presence of different electrolytes and in the presence of N03- where the initiating reaction is an electron transfer from nitrate to a nitrate radical (946).Caprolactam in waste water was determined by a dc technique (302). Data for 0- and p-substituted derivatives of benzamide in aprotic media (1151) and in the presence of proton donors (1152) were reported and correlated to u constants. Correlations were also reported for E1 2 data for substituted formamides, formanilides, and ureas (644) and substituted 3-arylmethylene phthalimidines, IIIb, a t p H 5-12 (1030)with substituent constants. The adsorption of nitriles on Pt was studied by cv techniques (26). The influence of adsorption in the reduction of acrylonitrile was noted (1102).Polarographic data were reported for several 4-substituted aromatic nitriles (896). Electrochemically generated radicals from fluorobenzonitrile were studied by cv techniques (477). The copolymerization of 2,4-tolylene diisocyanate with vinyl polymers was followed polarographically (816). Diisocyanates were determined in polyurethane formation (992). A correlation between E1 2 and substituent constants was found for 11 aromatic isocyanates (993). HALOGEN COMPOUNDS Reduction data were reported for bromo derivatives of methylcyclohexane ( 1 ) , dihalomethylene cyclobutane (2651, fluorinated derivatives of benzene, diphenyl, and

naphthalene (la),fluorine containing polyhaloethanes (378), meso and dl forms of (CBrC1F)z (379),several alkyl and aryl C-halogen compounds (926), and for haloethanes (989). The effect of Cu(I1) on the reduction of several organo halo derivatives (721) and of (Et)rNBr on the reduction of organohalogen compounds such as CeHsI, CHC13, and CC14 (723) was noted. Confirmational contributions were considered in a study of polyhaloethanes such as (CF2Br)Z (321). The production of lead alkyls a t a lead electrode in ethyl iodide-DMF solutions was examined by cv techniques (337). Three reduction processes for diphenyliodonium (914) and dibenziodonium ions and two for 4,5-phenanthryleneiodonium ion were noted (86, 749). A detailed electrochemical study of 2,2-dihalonorborane and several Schiff bases (927) was described. Benzocyclobutene dibromide (933), Diels-Alder adducts of dichloromaleic anhydride and cyclic dienes (808), and alkyl bromides and arylsulfonamides (216) were investigated by cv techniques. This technique was also used to study fluoroaromatic hydrocarbons in FS03H solvent containing HC2H302 (a base) a t low and room temperatures (207). Electrochemiluminescence studies, including cv data, were reported for 9,lO-dichloroanthracene (743) and 9,lOdichloro-9,lO-dihydro-9,1O-diphenylant,hracene (1006). Polarographic data were reported for bromo- and iodothiophenes (875), 22 C-halogens derivatives of 0-,m-, andp-carboranes (1029),and cyanuric acid (2212). Halogenated esters such as 2-naphthyl-2-bromo-N-alkanoates (596), BrCH2COO(CH2),0COCHzBr (653), 2-bromoalkylates for the homologous series benzyl phenyl ether, cyclohexyl, and cyclohexylmethyl esters (654), and 2-haloethoxy esters (983) were studied polarographically. The effect of proton donors on the reduction of chloroacetic and dichloroacetic acid and their esters in DMF was noted (502). The mechanism for the reduction of cis- and trans-cinnamic acid dibromides was discussed (682). Polarographic data were reported for allyl halides and 1-halopropenes (264), hexachlorocyclopentadiene (257), and for a-allenic and a-acetylenic aromatic halogen compounds in DMF (263). The reduction path for bromo-, chloro-, and iodobenzonitriles (66) and for cis- and trans3-chloro-2-arylpropenenitriles(675) was discussed. The effect of EtOH-H20 composition on El12 values for $iodo- and P-bromo-propionitrile and 1-chloro-2-iodoethane was studied (320). Experimental variables such as pH, supporting electrolyte, buffer, and solvent were considered in a study of a wide variety of substituted mono- and dihalo naphthostyryls (282-285). Half-wave potentials were reported for several different halo compounds in electrolysis studies of these compounds in the presence of different electrophiles ( 5 4 ) . Cathodic cyclization of acetylenic halides, such as Br(CH2)4CH=CHC6H5, were studied by cv techniques (779). The anodic trifluoroacetoxylation of hexamethylbenzene was studied by electrochemical techniques ( 1057). Half-wave potentials for 17 different chlorinated and ester compounds were reported in studies on their quenching effect on 1,4-dimethoxybenzene fluorescence (271). An equation relating to the rotation speed of a rotating disk electrode to Hg dropping rate was tested with /3-bromo- and 0-iodo-propionitrile (372). Correlations between E1 2 values for halogen-containing derivatives with dipole moment of the reducible group or solvent used (386) and E1 ) 2 values for substituted quinobromides with reaction rates of these compounds with morpholine (924), were reported. Procedures for the polarographic determination of DDT and y-hexachlorocyclohexane in aerosols (607), of the insecticide Nemagon (1,2-dibromo-3-chloropropane)(827), and for benzene hexachloride in feed and meat (845) were reported. The effects of pH on the reduction of N-bromosuccinimide (791) and of adsorption on the reduction of P-iodopropionitrile (332) were noted in the development of procedures for their determination. Hexachlorophene was studied by ac and dc techniques in buffered solution, and a procedure for its analysis was outlined (520).The herbicides Monuron, diuron, and fenuron in soil (638) and chloramp (331)were determined polarographically.

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NITROGEN COMPOUNDS Nitro Compounds. The reduction of nitrobenzene was used to illustrate kinetic waves in the presence of surface active agents (339), effect of the presence of organic anions and cations (3381, effect of supportin electrolyte (422), and the effect of proton donors in MeO% (851).Nitrobenzene reduction was studied at pH > 12.5 (170), as a function of pH by an op technique (364),in water-alcohol mixtures (954), and in acetone or dioxane by a dc and ac technique (1155). A splitting of the nitrobenzene wave at pH I 7 and the effect of pH, anions, cations, and nonionic compounds was noted (523). The prewave for the reduction of nitrobenzene and p nitroaniline in HC1 solution was suggested to be due to the reduction of a protonated species (953).The effect of ion pairing on reduction of nitrobenzene and anthracene in hexamethylphosphoramide (47) and of quaternary ammonium salts where one alkly group is ClsH3, on the reduction of nitrobenzene and nitrophenols (778) was discussed. Nitrobenzene and derivatives were studied as a function of pH and mixed solvent composition (1040).The effect of surfactants on ac data for nitrobenzene and nitrophenols (421) and of solvent composition and type of organic supporting electrolyte on reduction of nitrobenzene and nitrobenzoic acid (1055)was described. Reduction of nitrobenzene and p-nitrophenylacetic acid by an ac technique (2), 11 different substituted nitrobenzene derivatives (448), and p-nitrobenzoic acid (939) was studied as a function of pH. Nitro-benzenes, -benzonitriles, and -naphthalenes containing other substituents were examined in neutral and strong acid solution (537). p-Nitroaniline was reduced in alkaline media at a rotating Au electrode (891).The effects of buffer concentration on the reduction of nitro derivatives of benzene, toluene, and benzaldehyde were discussed (722). Polarographic data were reported for p-nitrostyrene and p-nitro-a$-dichloroethylbenzene (363), 0-,m-, and p-nitrostyrenes (365), 4-Cl-2NO2-CeH302CEt (397), m- and p-N02C&AsEt2 (496), p-substituted nitrobenzenes and substituted nitrofurans (1041), for p-iodonitrobenzene (587), and for 30 substituted mononitrobenzene and 30 substituted di- and trinitrobenzene derivatives (706). Adsorption of 0- and p-nitroanilines on Hg was studied (101). Reduction of nitrobenzene-rn-sulfonic acid was studied at different metal electrodes (574). The effect of ion pair formation and several electrolytes on reversibility for reduction of nitrobenzene was discussed (629). The reduction of p - and o-nitrophenol and p - and o-alkoxynitrobenzene was suggested to involve more than an ECE mechanism (225). All monohalogenated nitrobenzenes were studied in nonaqueous solvents and the reduction was shown to first involve halide elimination and hydrogen atom abstraction to yield nitrobenzene (804). A positive feedback resistance compensation by computer in cv was tested by studying p-nitrotoluene (1182). A method for processing data in linear sweep voltammetry was examined with rn-dinitrobenzene in DMF (498). Reduction data were reported for methyl indolyl nitroacrylate (49), Me2CHCH=C(N02)Br (211), 5-nitroorotic acid (;220),4-XC&N=NC&-N02-4 and -N02-2 (440), l-p-nitrobenzoyl-5,5-diethyl-barbituric acid (598), nitromethane (1111), and unsaturated nitro compounds (1209) as a function of pH. p-Nitrothiophenol reduction was studied in basic media (237). Polarographic data were reported for substituted nitrobiphenyl derivatives (266), nitrophenyl phosphate and phosphinate derivatives in ESR studies (417), nitro and dinitroazoxybenzenes (439), several aromatic nitro compounds in the presence of HC2H302 (529), nitrocellulose (774), substituted nitrobenzenes and nitroselenadiazole (1093), hydrazone of p-nitrobenzaldehyde (1131), nitrophenylhydrazine ( 1132), nitrovinylnaphthalenes ( 1156), nitroferrocene (1174), substituted p-nitro and p-amino benzophenones and diphenyloxides (I130), halonitroformanilides (1199), and the methyl ester of cu-nitro-P-(3-indoly1)acrylic acid (1208). A detailed electrochemical study of fifty 5-nitrofuran derivatives in different media (1039), of the anion radical of 4-nitrobenzylchloride (64),and of the anion radical derived from 2-bromo-2-nitropropane and the effect of pro56R

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ton donors (65)was reported. A pseudo-catalytic polarographic maxima observed in reduction waves for a series of aromatic nitro compounds in the presence of surfactants was investigated (751). Voltammetric data was reported for nitroalkanes in basic, buffered aqueous solutions, DMF, and in MeOH in electrolysis studies of their anions (1176). Conditions for NO2 removal from peptides by electrolysis was predicted from polarographic data (165). The pK, of Et-P-nitropropionate and -methoxynitropropane was determined by polarography (1088). Half-wave potentials for 4-substituted-2-nitro-2-hydroxy-5-methylazobenzenes at pH 3 to 12 (77), for 18 mand p-substituted nitrobenzenes (1094), and for seventeen 2,5-RR’CsH3N02 derivatives (1031) were correlated to substituent constants. Methods of interpretation of E1,2substituent correlations were evaluated and tested with reduction data for substituted nitrobenzenes and benzaldehydes and oxidation data for substituted anilines (6.58). A relationship between carcinogenic properties or rate constants for reaction with NaOEt for 4-nitroquinoline oxide derivatives was suggested (829).Energies for lowest triplet levels for 20 aromatic nitro compounds were correlated to their E112 values (347). A correlation between El12 values for mono-nitro derivatives of benzenoid hydrocarbons with HMO calculations or Hammett-Streitwiser constants was discussed (6.30). The kinetics of acetylization of aromatic nitroaldehydes (530),conversion of 5-nitroacenaplithene into the aci form (419), and the reactions of 1-nitrocyclohexene in alkaline solution (1202) was followed by polarography. Heterogeneous rate constants for the reduction of m-substituted nitrobenzenes were determined by an op technique (145). Stability constants for boric acid-nitropyrocatechol chelates were evaluated (425). Procedures for the polarographic determination of indolic auxins before and after nitration (128),aldehydes as 2,4-dinitrophenylhydrazine derivatives (772), 1,5-dihydroxy-4,8-dinitroanthraquinone and its 1,8-4,5-isomer (902), and for 2-isopropyl-4,6-dinitrophenol and 2,4-dinitrophenol in herbicides (782) after TLC separation were described. Polarographic data for 21 different nitroimidazoles and nitropyrazoles were reported as a function of pH and procedures for the determination of their mixtures were outlined (277). Mono-nitrobenzanilides (493) and 2(2-furyl)-3-(5-nitro-2-furyl)acrylamide in meat and fish (820) were determined polarographically. Nitroso Compounds. Nitrosobenzene (1154) and RzNNO, where R is different alkyl groups (122) was studied as a function of pH. Data were reported for an ac study of cupferron ( 5 ) , for various F and CF3 containing nitroso derivatives (368), for a cv study of 4-nitrosopyridine 1-oxide (938),and for 2,4-dinitrosoresorcinol (991). Nitrosation of 2-naphthol was investigated at Pt by a cv technique (515).Acid-catalyzed oxidation of p-nitrosopheno1 was followed by polarography (399). Capsaicin in ointments (127), styrene and a-methylstyrene (823),and phenol and 2-bis(4-hydroxylphenyl)propane (858, 859) were determined polarographically after nitrosation. Polarography was used to detect nitrosoamines in food and alcoholic beverages (1 184). Aliphatic-Aromatic Amines. Polarographic data are reported for catecholamines (318), for aminomethyl derivatives of 2,2-di(4-hydroxyphenyl)-propane(637),aryl aziridinium ions (557), 2,2,6,6-tetramethylpiperidinenitroxide and tert-butylnitroxide (1114), several iminoxyl radicals (@I), and diastereoisomeric sympathomimetric amines (298). The reduction mechanism for 7 different imines in MeCN-DMF was reported (18). Adsorption of 18 amine oxides at the DME was investigated by ac and op techniques (454). The polarographic activity of 36 tosyl derivatives of aliBhatic and aromatic amines and amino acids in DMF was recorded (719). One of the anodic waves found for alkyl amines was shown to be due to adsorption (742). Several solvents were used in the study of stable radicals derived from 2,2,6,6-tetramethylpiperidine-l-oxyl (1049). The effect of structure was considered in a cv study of 21 different tertiary amines containing 1to 4 N-atoms (806). Ethylenediamine in ammonia was determined polarographically (114). The catalytic H-wave for hexamethyl-

enetetramine solutions was used for the determination of the amine (1099). The polarographic behavior of quaternary ammonium halides (143, 624) containing alkyl, aromatic, and heterocyclic groups (813) was described. The effect of tetraalkyl ammonium cations on the catalytic H-wave in amine solutions was noted (715). Tetraalkylammonium trifluoromethane sulfonate was examined as a supporting electrolyte in DMF, MeCN, CH2C12, and T H F (945). Propylene carbonate was used in a cv and dc study of NH4+ in the presence of the macrocyclic ion carrier nonactin (25).Micelle formation for the surfactant RN+MeZ(CH2)nN+Me2Rwas studied by an ac method ( 4 ) . Detailed electrochemical studies were reported for the oxidation of N,N-disubstituted p-toluidine (60), 34 condensed aromatic amines such as anilines, naphthyl amines, aminoanthracenes, etc. (74), aniline a t rotating carbon paste electrode (279), orthanilic, metanilic, and sulfanilic acids a t Pt and C paste (248), and anilinopropionic acid and 14 of its derivatives (1198).3,3’-Dimethylnaphthidine was studied by a cv technique (657). Data by a cv technique for triphenylamine and N,Ndimethylaniline in a AlC13-NaC1 melt was compared to data in MeCN (690). Twenty-one different 4-substituted triphenylamines and their radicals were investigated (219). A cv study of the electrolysis of 2,4,6-tributylaniline in the presence of pyridine nucleophiles was reported (176). The anodic oxidation of aniline in MeCN was suggested to occur through dimers of benzidine and p NH2C6H4NHC6H5 (131). Electrode filming by anilines was shown to increase by cv techniques for certain kinds of substituents on the aniline ring (910). Detailed electrochemical studies including cv techniques were reported for N,N,N’-triphenyl-o- (87), N-phenyl-p- (174), and N-substituted p - (184) phenylenediamines. Oxidation data were listed for N,N-dihydroxyphenylenediamine (226), di-p-anisylamine and its N-methyl derivative (185), and for N,N,N’N’-tetramethyl-p-phenylenediamine in the presence of Na2S03 as a function of pH (301). The effect of solvent on E112 for a series of o-phenylenediamines was noted in electrolysis studies which lead to cyclization (dihydr0phenazine)formation(186). Autooxidation of p-phenylene was followed polarographically (214). Aromatic diamines (593) and xylenediamines and aminonitriles (33)were determined polarographically. An ECE mechanism was suggested for the oxidation of 4-aminodiphenylamine and variamine blue in propylene carbonate and MeCN; the effect of acids and bases was also noted (311, 950, 951). The oxidation path for 2,4-diamonodiphenylamine was studied in acid solution (312). Data were reported for (RC&)zNH, the corresponding cyclized dihydrophenazine, and tetraarylhydrazines (175). Oxidation data were described for N,N’-diphenylbenzidine in MeCN (173) and for N,N,N,N-tetramethylbenzidine in MeN02 (241). A cv technique was used to study and determine benzidine in thin layer electrochemistry (329). The benzidine rearrangement was followed polarographically (670). Correlations were reported for El12 potentials for 46 substituted aniline derivatives with LCAO calculations (705), for 11 p-substituted (including Si and Ge groups) N,N-dimethylanilines with ionization potentials (536) and for aniline and hydrazine derivatives with Hammett u values (1091). Azo Compounds. Polarographic data were reported for diazonaphthols (254, 1070), 4-hydroxy monoazo compounds (509), hydroxy-, methyl-, and amino-substituted azobenzenes (948), 1-phenylazo-2-naphthylamine in the presence of Co(I1) (961), 1,8-diazoniaphenanthrenes,1,5diazoniaanthracenes, and 1,5-diazonianaphthalenes (1087), o,o’-substituted azo compounds (1108), and naphthyl-azo-quinoline derivatives (1196, 1197). The effects of weak and strong proton donors on reduction of substituted azobenzenes (125, 126), of adsorption in the azobenzene-hydrazobenzene system (879), and of the presence of surfactants in reduction of azobenzene (1181).Diffusion coefficients for several azo dyes were determined polarographically (360). Azobenzene was used as a model system to measure the chemical reaction rate in an EC mechanism where both electrode reactant and product are adsorbed (1138).

Hammett o - E ~12 correlations were reported for substituted o-(dialky1amino)benzenediazonium salts (113), p substituted azobenzenes and 2-substituted-5-phenylazopyridines in. DMF (633), and for substituted aromatic diazo compounds (821). Relationships between E l / z data for mono-substituted azo compounds in MeCN with Hammett u constants, n-x absorption frequencies, and theoretical energies for the lowest vacant r-molecular orbital were described (759). Azomethines. Substituted N-benzvlidene-D-anisidines were studied by a cv technique in“ MeCN’ (739) and MeCN-1% py (740). Polarographic data were reported for IVa (23),IVb (24),

Ab. R = Py

azomethine derivatives of 2-nitrofurfural and @-(5-nitro2-fury1)acrolein (1042), and for p-methoxybenzilidene-pbutylaniline (243, 244). Oxidation and reduction data where listed for the liquid crystal N-(p-methoxybenzy1idene)-p-n-butylaniline in DMF where the reduction leads to a radical anion which decomposes by both an EC and ECE mechanism (692). Dimethylaniline in dimethylacetamide was determined polarographically after reaction with H2CO (34). Half-wave potentials for hydroxybenzylideneanilines were correlated to LCAO calculations of electron density (610) and lowest molecular orbital free energies (98).A relationship between g constants and dc and cv data for RCeH4CH=NN=CHC6H4R’ derivatives was reported (586). Oximes. Isatin-3-oxime (20, 22) and quinone dioxime and o-methyl-p-benzoquino monoxime ( 115) were studied as a function of pH. Polarographic data were reported for HON=CRC6H50CHR’COPy (236), cu-chlorobenzaldoximes (398), phenylhydroxylamine and the influence of adsorption (449), hydroxylamine a t various rotating metal electrodes (575), coordinated oximes, such as dimethyl glyoxime (DMG) and cyclohexane-1,2-dione dioxime (799),and for DMG and several of its analogs (1005). An equation describing irreversible polarographic and voltammetric curves involving protons was tested with DMG (415). The pK, values for substituted phenylhydroxylamines (224) and pentachlorobenzaldoxime (788) were determined polarographically. Hydrazones, Hydrazines, and Semicarbazones. Oxidation of MeNNHz in alkaline solution (290) and at a mirror bright Au electrode (291) and of’ phenylhydrazine as a function of pH and supporting electrolyte (1013) was studied. Triphenylhydrazine (177), 1.1-dimethylhydrazine ( I 7 8 ) , bicyclic diazenium salts and determination of its acidity (807), and 25 tetraalkylhydrazines and a determination of inductive and conformational effects (805) were examined by cv techniques. Half-wave data were reported for 19 N-nitrosoamines and their hydrazines derived from alkyl, aryl, and heterocyclic groups (512). The acid-base properties of hydrazone formation (1123) and benzophenone hydrazone (61) were studied polarographically. The technique was used to detect N-formylN-methylacetaldehydrazone (Gyromitrin) in mushrooms (110).

The effect of proton donors, electrolytes, and substituents and the mechanism for the reduction of diazoaminobenzenes was reported (460-464). Oxidation data were described for l-aryl-3,3-dialkyltriazene compounds (1217 ) . Terephthalic acid hydrazide and isophthalic acid dihydrazide was studied as a function of p H (85). Data were reported for 1-Dhenvlthiosemicarbazide (1I07), several thibsemicarbazone der[vatives a t a graphite electrode (700), for C6H5C(=NNHCONH2)C6H5 (37), for C6H5C(=NNHCO”2)COR (2751, and for p RCsH4CH=NNHCONH2 (430).

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UNSATURATED HYDROCARBONS Voltammetric data were reported for 4,4’-dimethyloxybiphenyl 9,lO-di-p-anisylanthracene and thianthrene (429), 9,lO-diphenylanthracene (432), 9,lO-di-n-propyl anthracene in the presence of CN- which leads to a nitrile product (854), and for anthracene a t a rotating disk electrode (579). Adsorption on 9,lO-diphenylanthracene and its radical anion on Pt was examined by a cv technique

studies of a,/3 unsaturated compounds in which an anionic species from the unsaturated compound is generated and undergoes a reaction with an alkyl halide (1004). An ECE mechanism was reported for the two-wave reduction of l,l-dimethyl-2,3,4,5-tetraphenyl-l-silacyclopentadiene (1068) and for 5 different azabenzenes (835).Data for fluorene and fluorene carbanion was compared to data for alternate hydrocarbons and it is suggested that the reduction path involves a 3-e change per molecule of fluo(441). rene under protic conditions yielding reactive intermediRates of protonation of anthracene and 1,2-benzanthraates rather than the usual 2-e electron reduction a t a doucene radical anions in DMF were calculated from polaroble bond (533). graphic data (ECE) (354). Reduction of anthracene by cv A cv technique was used to determine pK, values for generation of solvated electrons in presence of proton doweak hydrocarbon acids (132-134, 200). Redox data by a nors was studied (48). A polarographic cell containing opcv method were reported for several hydrocarbons in DMF tically transparent electrodes was used to study anthrain electrogenerated chemiluminescence studies (313). Ancene and perylene radicals as they form in the cell (452). odic data for several simple alkanes were obtained in Oxidation-reduction data were reported for polynuclear FSOaH-carboxylic acid solvent mixtures (89).The polarohydrocarbons a t Pt in HzS04 (67), several polycyclic arographic properties of the carcinogenic photoproducts of 3matic hydrocarbons in molten Bu4NtC104- at 150 “C methylcholanthrene were discussed (831). (232),disubstituted 9,9’-bifluorene a t the DME and rotatMercuration of l,4-cyclopentadiene (172) and the role of ing Pt (262),and for phenylated naphthalenes (475).Acesolvents in the reaction of Xa(Hg) with vinyl polymers naphthylene, fluoranthene, and 2,4-dimethylaceheptylene (733) was determined polarographically. Analytical proce(1200), 7 different aromatic hydrocarbons in CHzCl2 a t dures using dc polarography were reported for acenaph-70 “C (156). 2,3,6,7-tetramethylnaphthalene(934), and thylene (124), acrylamide and styrene in copolymers tetraphenylethylene and 9,lO-diphenylphenanthrene (641), acrylonitrile in extracts of styrene-acrylonitrile co(1047) were studied polarographically. Half-wave potenpolymers (878),and for fetidine in plants after TLC (920). tials for 8 helicenes were used in a discussion of coplanarHammett u - E ~2 , correlations were reported for ozonides ity (652). 2,5-Diphenyloxazole and 2,5-diphenyloxadiazole of substituted stilbene and ring substituted styrenes (402) were used as solvent in an electrochemiluminescence and for substituted fulvenes (1063). HMO calculated study of aromatic hydrocarbons (567). energies-& 2 correlations were reported for the oxidation Perylene in electrochemiluminescence studies (393). 4of several aromatic hydrocarbons (438, 578), arene anions methoxystyrene (786), styrene, methylstyrene, and indene and polymer anions (793), p-substituted triarylmethyl (977), and triarylmethane (809) was studied by a cv techcarbonium ions (also to u values) (1044), fulvene derivanique. tives ( 1 0 6 4 , and to methyleneindene and methylenefluoPolarographic data were reported for triaryl derivatives rene derivatives (1065). Half-wave potentials for 21 substiof 1,3,5-trivinylbenzene (619), 4,4’-dialkylbiphenyls (814), tuted tropenylium ions were related to charge transfer substituted tropylium ions (828), [Blannulene (837), 2substituted norbornadienes, bicyclo[2.2.0]octa-2,5-dienes, band measurements (401). and 4-substituted [2.2]-paracyclophanes (1003), diarylalPEROXIDES kanes, and paracyclophanes (1187)and for V (487). Polarographic data were reported for polymeric peroxides (1117). The effect of substituents in perbenzoic acid c1 was considered in a cv study (1149). Polarography was used to detect peroxide intermediates in the electrooxidation of PhMe, PhEt, and PHCHMe2 (1025). Rates of epoxidation of isoprene by perbenzoic acid were correlated to E1 / 2 data for mixed solvents (42). V

VI

Trichloro spiro [2.3] hexadienyl anions derived from VI (982),carbanions such as (C&15)&1C- and (CI&)~C- in basic DMSO (691), and mono-, di-, and tricarbonium ions, carbanions, and radicals of the triphenylmethane series (616) were studied. Pulse radiolytic polarography of short lived radicals, such as CHOHCH3, CH&( .)HOH, and .CH(OH)2, and others was examined polarographically (395, 396). Tropylium reduction a t DME and rotating Pt was used to produce radicals for an ESR study (890).The mixture MeN02-A1C13 was tested as a media for studying organic radical cations derived electrochemically from aromatic hydrocarbons (68). Polarographic data for p-MeOCsH4CfMeZ (63), C1(C&15)2C. (240), benzoyl-1,4-bis(diphenylcyclopropeny1ium)dication (289), triphenylmethyl type cations (319), and for [R4N (or P)]+ [cyclooctatetraene]- and [R4N (or P)]z+[cyclooctatetraene]2- (676)were reported. Cyclooctatetraene (1079) and its benzo and sym-dibenzo derivative (16, 931) were studied polarographically. Polarographic data for cis- and trans-bicyclo(6.1.0)nona2,4,6-triene, cis-bicyclo(6.2.0)deca-2,4,6-trienewere obtained in order to test for homo aromaticity (15). Olefins were studied anodically a t Pt and C rods (563). Propylene in MeCN (202) and ethylene oxidation a t a Au electrode (754) were studied by cv methods. The mechanism for the reduction of activated olefins (electrodimerization) was discussed in detail (17, 19, 915). Chemisorption of olefins and metal chelates containing an olefinic side chain on Pt electrodes was studied electrochemically (661, 662). Half-wave potentials were reported in electrolysis 58R

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SULFUR COMPOUNDS Mercaptans, Sulfides. A catalytic wave in ammonical Co(I1) solutions was observed for cycloserine (157), thiamine and its disulfide form (870),ethylene bis(3-mercaptopropionate) (974), methionine and methionine iodomethylate (996),and for unithiol (1106).A double wave was found for cysteine under the’ same conditions a t a hanging Hg drop (30). Cystine and cysteine were studied by op as a function of pH in the presence of Cu(I1) and Cd(I1) (766). Polarographic data were reported for N,N’-dibenzenesulfonyl-Lcystine (367), cystine as a function of pH (507), and for 2-mercaptopropionyl glycine (846). The effect of adsorption on the polarographic behavior of the cystine/cysteine redox system was studied in detail (762). 2-Mercaptothiazoline (559), 2-dimethylaminoethanethiol (769, 770), glycol dimercaptopropionate (970, 973), diisopropylaminoethanethiol (971), furfuryl mercaptan (975). and 0-mercaptopyruvic acid (1096) was studied as a . . function of pH. PolaroeraDhic data were reported for the reduction of n a p h t h a h e compounds coriaining different S groups (1192),of thiamine, tetrahydrofurfurylsulfide, -mercaptan, and -thiosulfate, and sulfothiamine (43), and for the oxidation of thio-8-hydroxyquinoline (90). Oxidation and reduction data were reported for HSCH2CH(SH)CH2S03Na and unithiol bisulfide (1203). The pK, value for thiolacetic acid was determined polarographically (976). Mercaptans in pulp waste water were determined (1214). Other methods for determining S H grou were com ared to the polarographic method (1180). &e reaction getween MeHgI and mercaptopyrim-

idines and mercaptopurines was followed polarographi. - tally (699). The enol-keto equilibrium for 3-p-tolylthio-2-keto-proDanoic acid (341) and for a-mercaptopvruvic acid where the two forms are reduced by diff&ent paths (342, 343) was studied polarographically. Voltammetric data were reported for 2-mercaptobenzothiazole in an electrolysis study (187). Diphenyl sulfide was studied by cv techniques in H2S04 solution (471) and MeCN (713). Oxidation of phenyl disulfide (1105) and the effect of supporting electrolytes (119) was noted. Polarographic data were reported for several disulfides (618), a&- and @,P’-dithienyl disulfides (716), and @$’-dithiobis(pyruvic acid) (1095). A 2-electron reduction of substituted aryl diphenylmethyl sulfides and a correlation of the data to a constants was reported (308). Mercapto groups in milk (783), thiuram E (615), and disulfiram (904) were determined polarographically. Products of the electrolysis of thioethers in MeCN were studied by polarographic methods (333). Sulfur-Oxygen Bonded Compounds. Polarographic data were reported for aromatic P-disulfones (392), thianthrene, its monoxide, and thianthrene sulfone and its dioxide (499), gem-trisulfones of the type (XC ~ H J S ~ ~ ) ~ C(531), H S ~and ~ Rcyclic sulfones (659). Dimethyl sulfoxide was studied by photopolarography (497). The effect of substituents and the reduction pathway was described in a study of several substituted phenyl methyl sulfones (1010). Half-wave potentials were reported for 28 compounds containing sulfonyl, sulfinyl, sulfonium, and related S-substituents as a function of pH (479). Hammett u-Ell2 correlations were reported for substituted aromatic sulfones and alkyl p-toluenesulfonates (362) and aryl sulfonates (1158). Energies for lowest unoccupied molecular orbitals were correlated to Ell2 data for 14 sulfones (239). Hueckel MO calculations were used for studying and predicting the polarographic behavior of a,@-unsaturatedsulfonyl chlorides ( 8 0 ) . Polarographic data and procedures for the analysis of chlorinated toluenesulfonic acids (330) and S, S-diphenylsulfoximes (457). Aryl-sulfinates and thiosulfonates (408) and p-toluenesulfonic acid (836)were determined by an ac technique. Lignosulfonic acids (729) and anionic sulfate and sulfonate surfactants (998) were determined polarographically. A dc technique was used to study the effect of Na-alkyl (C8-cl8) sulfates on polarographic maxima (639) and a cv technique was used in a study of electrolyte effects on a dodecyl derivative (730). Thioacids. Detailed electrochemical studies of alkali metal alkyl xanthates were reported (268, 269, 621). The impedance a t the DME in KEt xanthate solutions was measured (865). Poisoning of Pt electrodes by xanthates was studied by cv (800). Potassium isopropyl xanthate was determined by pulsed oscillographic polarography (384). The electrochemical behavior of diethyldithiocarbamate in mixed ternary solutions was reported (149). Diethyldithiocarbamate, urea, and 5-mercapto-3-phenyl-1,3,4thiadiazole-2-thione were studied in the presence of metal ions (388). The anodic behavior of diethyldithiocarbamate and dithiothreitol were studied a t fast drop times; it was found that surface effects, maxima, and erratic drop time due to adsorption of reaction products on electrode surface were reduced and consequently more reproducible calibration curves and subsequent analyses were improved (164). Ethylthioglycolate was studied as a function of pH in 40% ethanol (968). The catalytic H-wave for ethylthioglycolate in ammonical CoCl2 solution was studied as a function of experimental parameters (969, 972). Polarographic data were reported for ammonium 1-pyrrolidinecarbodithioate and 2-carboxy-1-pyrrolidinecarbodithioate (588), for thioacetic acid oxidation (640), dithiobenzoate and dithioacetate a t DME and Pt as a function of pH (988), for thiobenzoic acid in mixed solvents (1092) and for aromatic mono- and disulfonyl chloride reduction (1159). The oxidation path for 0-ethylthioacetothioacetate and 0-ethylthioacetate in acetone was shown to involve Hg ( I 18). Thioketones, Thiocyanates. Polarographic data were

reported for 12 mono-thio-P-diketones (414), 2-a-ethylthio-substituted ketones (777), and for thiourea on a graphite electrode (1207). The effect of substituents and steric hindrance was considered in a cv study of phenyl and anisyl substituted 1,2-dithiol-3-thiones (869). Tetrazole-5-thione (389) and 5- and 3-triazolethiones (390) were studied by an op technique. Polarographic data and effect of proton donors on p vinylphenylisothiocyanate were reported (815). Isothiocyanates containing azo, carbonyl, and carboxyl groups (79) were determined polarographically. A Hammett o-El 2 correlation was reported for 33 p-XC6H&C,&I4NCS-p derivatives (737). ORGANOMETALLIC COMPOUNDS Voltammetric data were reported for metal hemiporphyrazines (106), lead porphyrins (323), octaethylporphinatosilver(LI)perchlorate (542), Vitamin B-12 and Co-porphyrin compounds (681), and the reduced form of chlorophyll (623). Oxidation of chlorophyll and a study of the cation radicals that are produced were described (609). A 2-electron reversible step and the role of proton abstraction in the reduction of Zn-tetraphenylporphin was reported (663). The reduction of Co-porphin complexes in the presence of pyridine where it acts as an axial ligand was described (234). Redox data and the effect of the metal were reported for 25 metallporphyrins with different central ions (352). Polarographic data were reported for 15 compounds of the type C6H5Fe(CO)LR (247), 1,2-bis(diphenylphosphino)ethanebis(r-cyclopentadienylcarbonyliron) (322), and R C B I O H ~ O C F ~ ( C O ) Z Cand ~ H ~ its reaction products (1206). The ferriheme/ferroheme system (541), several bridged biferrocenes ( 7 8 I ) , ferrocene polymers (796),ferrocenyl carbonium ions (1089),and ferrocene, ruthenocene, and osmocene (410, 524) were studied by dc and cv methods. Polarographic data were reported for 24 symmetric organic Hg(I1) compounds of a - and @-substituted 5-membered heterocyclics (151), organomercury salts and mercury derivatives of ferrocene, cyclopentadienyl manganese, and rhenium tricarbonyls, and o-carborane (246), of 2 acetylthiophene derivatives brominated and mercurated in the 5-position (556),trans-oxymercurated allenes (560), ( C & , ) & g and effect of electrolyte concentration (8?8), and for 2-chloromercuri-3,3,3-trifluoropropanol-l(895). The reduction of perfluorodiphenyl mercury and perfluorophenyl-mercurous bromide and the influence of adsorption was noted (303). The reduction path for (RHg),X where R is an alkyl or substituted aryl group (955) and for bis(2,5-diphenyl-1,3oxazol-4-y1)mercury (1019) was described. Voltammetry was used to study the dimerization of organomercury radicals (672). Two waves were described for o-hydroxyphenylmercury chloride in aqueous “ 0 3 (789). Two 1-electron reduction steps were suggested for 2-(piperidino)ethylmercuric chloride and 2-(diethy1amino)ethylmercuric chloride (1172). Polarographic data were reported for several alkyl and aryl tin chlorides and bromides in a variety of solvents (1125, 1126), for di-tert-butyl dichlorotin (6771, and for several different organo-tin compounds and their decomposition products (1189). Formation of acetate complexes was suggested in a polarographic study of C2H5SnC13 in acetate buffer solutions (250). Three cathodic waves were reported for MezSnC12 (121I ) . Procedures for the determination of bis(tri-n-butyltin) oxide and di-n-butyltin oxide in soft woods (1185, 1186) and triphenyltin acetate in potato leaves (217) were described. The reaction between EtSnI and Hg(I1) was followed polarographically (534). Substituted cyclopentadienylcobalticenium salts (293) and mono- and di-substituted cobalticenium salts (294) were studied. Polarographic data were reported for several organo-cobaltamines (679), alkyl substituted Schiff basecobalt complexes (680), and for the cobaltocene-cobalticenium system in pyridine (50). The catalytic prewave for Ni(I1)-selenocystine ( 258, 159) and for Ni(I1)-pyridine and alkylpyridine (728, 1221, 1122) systems was studied. A cv study of Ni and Cu complexes of the macrocycle 5,7,12,14-tetramethy1-1,4,8,11-

A N A L Y T I C A L C H E M I S T R Y , VOL. 46, NO. 5, A P R I L 1974

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tetrazacyclotetradeca-4,6,11,13-tetraene was reported (1113). a-Diketone-bis(thiosemicarbazone)copper(II)complexes were studied (1175). An op technique was used to in the presinvestigate 2,6-dioxo-1,2,3,6-tetrahydropurine ence of copper ions (387). Oxidation or reduction data were reported for transition metal (Pd, Pt, Ir, Rh, Ru) carbonyl complexes of tetrachlore-o-hydroquinone (%), Ru(I1) complexes of tetraphenylporphine and other porphine derivatives (140), for the catalytic wave in rubeanic acid-RuCl3 mixtures (459),and for r-allylrutheniumtricarbonyl bromide (1135). Voltammetric data were reported for Ru(bipyridine)aClz in electrochemiluminescence studies (1097). Four waves that were found for trimethylplatinium(1V) was explained (942). A 2-electron reduction of trans-ClRh(C0) (Ph3P)z leads to Rh- anion which immediately reacts with starting material to form a Rho complex (885). cv Investigations were reported for metal o-ethylthioacetothioacetato complexes (117), bis(maleonitri1odithio1ate)cobalt complexes (222),,quaternary organo antimony ions MemPhd-m Sb+ (599, cation radicals for group IV (267), Mn( CNMe)6+ and substituted anilines Mn(CNR)e+ where R is an aryl group (1110), and diphenylthallium (1210). Ethyltrichloro-Ge(1V) was studied at pH < 4 (210) while dimethoxy ethane was used as solvent for triphenylgermanium halides (112). Polarographic data were reported for triphenyl lead hydroxide and diphenyl lead diacetate (208),for phenyltriacetatoplumbane (209), and for alkali metal and T1 complexes of macrocyclicpolyethers (611). The effect of R in oxidation studies of RMgCl in T H F was investigated (191). A 1-electron reduction was suggested for (*-Cp)zTi(R)Cl where Cp = cyclopentadienyl and R = C1, Me, Ph, C5F5, OTiCl(r-Cp)z (193). Polarographic reduction potentials were reported for 80 complexes of the type LMoPR3(C0)3 and LMo(PR3)2(C0)2 where L = substituted glyoxal or diacetyldiimines and camphorquinone monoimine and R = Ph or Bu (1101). Phosphorus, Silicon, Boron, Selenium, Arsenic Compounds. Reduction data were reported for 8 phosphazene ~ E ~ )and ~ derivatives (8), ~ - R C ~ H ~ C ( = N Z ) P ( O ) ((539), 0-,m-, and p-isomers of BloHloPCH and BloHloAsCH in DMF (1204, 1205). Radical anions of phosphazene (107), phenylcyclopolyphosphine (280), and phenacyltriphenylphosphonium salts, benzhydryltriphenylphosphonium salts, and triphenylphosphine (963) were studied by cv methods. Several organophosphorus anion radicals such as Ph3P. - were generated polarographically for ESR studies (494, 495). Chemical cleavage rates and reduction data were correlated for ~ - R C ~ H ~ C O P ( O ) ( OatE ~pH ) Z 5 to 8 (538). Two different products, depending on whether one or two electrons are transferred, were found in a polarographic study of 1,4-diphosphonia-2,5-cyclohexadiene salts (932). The effect of azobenzene, azoxybenzene, and nitrobenzene on desorption of Ph3PO was studied by ac polarography (418). Organophosphoric insecticides (490) and methylnitrophos in plants and soil (863) were determined polarographically. Polarographic detection was used in an enzymic determination of organophosphorus insecticides (231). Oxidation of phenoxaselenin (183) and PhSeSePh as a function of pH (760) was studied. Reduction data for p RCsH4Se02H derivatives were correlated to u constants (1150). Polarographic data were reported for VI1 and VI11 (211) and for IX (286)in ESR studies. Pr

I

w

WI +

Ix 60R

*

A N A L Y T I C A L CHEMISTRY, VOL. 46, NO.

5, APRIL 1974

Polarographic data were reported for dimethylsilyl and methylene bridged aromatic compounds (215), trimethylsilyl substituted naphthalenes (304), and a-naphthyl and phenyl substituted polysilanes (889). Hydrolysis of R3Si(CHz),SCH=CHz was followed polarographically (1161).

BIOLOGICAL-PHARMACEUTICAL STUDIES The references in this section are those which emphasize investigations or the determination of biological and pharmaceutical compounds. These references were not cited in any of the functional group sections. For completeness, the reader should examine the functional group sections for additional references pertaining to the biological-pharmaceutical area. Biological Compounds. Polarographic data were reported for 14 amino, acids in DMSO (594) and dehydroalanine (979). Oxidation of tyrosine and @-(3,4-dihydroxyphenyl)-1-alanine was investigated in HzS04 by cv methods (589). An hydrogen catalytic prewave for selenocysteine-Naf solutions was investigated as a function of variables and used for analysis (1164). The equilibrium between glycine and glyoxal (1147) and iodinated amino acids after nitration (1171) were determined by polarography. The polarographic determination of p-chlorophenylalanine was used in a study of the interrelations between sleep and sexual functions (936). Polarographic data were reported for nicotinamide and its N-substituted derivatives (1071, 1074-2076) and nicotinamide and nicotinamide mononucleotides and dinucleotides (959, 980). Three waves were reported for isonicotinic acid in a study of experimental parameters (162). 2-Hydroxynicotinic acid and its N-1-riboside metabolite in blood and urine (39) and nicotinic acid and cinchomeronic acid (161) was determined. The synthesis of nicotinic acid and nicotinamide from 3-picoline was monitored polarographically ( 75). Detailed electrochemical stddies of the reduction pathway were reported for pyrimidine (297, 834, 1072, I141), cytosine, cytidine, and 2-pyrimidone (220, 221 ), allopurinol as a function of p H (235), adenine and adenosine (273), and for alloxan and methyl- and dimethylalloxan (434). Pyrimidine was investigated by drop time controlled polarography and a cv technique a t a DME and stationary vitreous C electrode (1077). The electrochemical behavior of folic acid, 7,8-dihydrofolic acid, and tetrahydrofolic acid were studied as a function of pH (626, 627). The oxidation of purines (271) and uric acid and xanthine (272) at a pyrolytic graphite was suggested to parallel biological enzymatic oxidation of the compounds. Voltammetric data were reported for flavin mononucleotide (14), 5-methyl-2-thio-6-azauracil (897), bilirubin (1140), and for cytosine, cytidine, cytidine monophosphate, and CPC (1178). Oxidation and reduction of ubiquinone 6 , Vitamin K3, and dihydrovitamin K3 was related to mitochondrial respiratory action (181). Voltammetric data for cysteine, glutathione, ascorbic acid, and cystine were recorded in attempts to monitor these in organs in vivo (612). Methods for the determination of guanine (270), serum uric acid (852),uric acid and allopurinol (274),lipid oxidation (223),and pyridoxal hydrochloride (1026)were described. A discussion of the polarOgraphy of proteins (70, 645, 647), double helical synthetic polynucleotides (94),and for heat denaturation of whey protein (795) was cited. Polarographic data were reported for ADP (673), native and denatured DNA (842), calf thymus DNA (843), and chemically methylated DNA (922). A continuous cv determination of AET and its metabolites in animal organs in vivo was described (908). Protonation effects of homopolynucleotides (840) and the catalytic maxima for tobacco mosaic virus (947) were studied in detail. Enzymatic degradation of mammalian and bacterial DNA (930) and the adsorption and association of di- and oligo-nucleotides (1177) was studied by dc and ac techniques. Catalytic currents were studied in detail for nine different proteins (548), bovine serum albumin (601), and for trace levels of nucleotides (1023). Procedures for the de-

idine (906) were examined as a function of pH. termination of serum proteins by a catalytic wave in The effect of substituents for 34 sulfonamides (1051) trans - d ic hloro -bis(N,N’-dimethylethylenediamine)Rh(IIand cv data for the oxidation of N, N-dimethylmethan1)chloride solutions (6) and for nucleotides by a catalytic esulfonamide (941) were reported. Three waves were wave in Cu(II) solutions (1022) were reported. Brdicka found for the copper complex of 3-ethoxy-2-oxobutyralconditions were used to determine protein in blood serum dehyde bis(thiosemicarbazone), an antitumor reagent of men with blood cancer (714). Nucleic acids (81, 841), (2.3.3, and for d-threo-1-(4-nitrophenyl) -24azidoacetamipyridine nucleotide in blood (1034), and the binding bedo)propane-l,3-diol (883). An op technique was used to tween azo dyes and proteins (725) were determined by POstudy adrenaline, noradrenaline, and serotonine (147). larography . The effect of adsorption was noted in reduction studies Ascorbic acid and related compounds in food (545, of quinazoline and its 2,3- and 3-phenyl derivatives (882). 1168) and the decomposition of 1-dehydroascorbic acid The anodic range of a carbon paste electrode was tested (1146) were determined by polarography. Procedures for with lidocaine, prilocaine, caffeine, and adenine (686). the analysis of ascorbic acid in meat and foods (228, 546) Binding between 2-(4’-hydroxybenzeneazo)benzoic acid and dehydroascorbic acid in food (229) after reaction with and a-(4-chlorophenoxy)-a-methylpropionicacid in serum o-phenylenediamine were described. A pulse radiolytic albumin (192) and acetylation and formylation of 21-iodopolarographic (394)and cv and dc (135) study of ascorbic 17-a-hydroxyprogesterone(258) was followed by polarograacid was reported. phy. Esterase and lipase after reaction with P-naphthol and Procedures for the polarographic determination of 2-ninitrosation (230), p-nitrophenylphosphatase (769, pyritrofuran derivatives (918), a-(5-nitro-2-furyl)-/3-nitroethydoxal 5’-phosphate membrane adenosine triphosphatase lene (1043), benzimidazole group drugs (862), Dimetridaand phospho lipids (925), binding in glycogen phosphorylzole (1,2-dimethyl-5-nitroimidazolein animal feeds and ase B (978), xanthine oxidase in milk (1081), glucose oxisamples (9, 1035), and chloroamphenicol (881, 919). An ac dase in culture liquid (404, and starch in food stuff after method was used for the analysis of nitro drugs such as reaction with glucose oxidase (1112) were determined POnitrofurazone, furazolidone, Zoalene, dimetridazole, and larographically. Oxygen uptake by glucose oxidase (771) Ronidazole (453). A flow through micro cell was used in and micro oxygen levels in water after reaction with flavin an ac and dc determination of bromophenindione, trihyenzyme (832) were determined by a dc method. Adsorption droxyethylrutoside, glibenclamide, and coenzyme A of native ribonuclease on the DME was noted (864). (1008). Mutarotation of d-glucose (346) and of d-xylose (491) Diazepam in blood (328, 518) and in pharmaceuticals and the catalytic activity of alkaline 8-lactoglobulin as a (517), Nitrazepam in drugs (427), Oxazepam and Lorafunction of time (822y was followed polarographically. Mozepam in several formulations (380, 1032), and benzodinosaccharides in unbuffered solution (492) and 3-keto sugazepine and 4-hydroxybenzoic acid esters as 2,4-dinitroars as a function of pH, incubation time, and H3B03 conphenyl ethers (1067) was determined polarographically. centration (1134) were studied. Procedures for the polaro2-Chloro-4-nitroformanilide in blood and urine (643) and graphic determination of glucose (532), carbohydrates in 5,2’-dichloro-4-nitrosalicylanilide (952) were determined. wheat flour (873), and of saccharin in milk (1060) were rePolarographic analysis of l-p-nitrobenzyl-5,5-diethylported. barbituric acid (544, nitranol and nitrosorbide (403), 5Polarographic data were reported for rifampicin as a nitro-8-hydroxyquinoline,and its 5,7-dichloro derivative function of pH (361),for poly(adeny1ic acid) (526-528), ri(819), nitrourea and isoindolinenitrourea (880), bromoisobolibrium and its hydrolytic prducts (949), riboflavine and valerylurea and bromodiethylcarbamide (1139), tolbutamits reactions with metal ions in DMSO (967),and d-gaide and chloropropamide (IO%), Vitamin K1 (1045), Vitalacturonic acid (1015). Factors that influence the catalytic min A in cod liver oil (252), phytin (642), and codeine (52) reduction of d,l-lupanine were described (1109). T’issues was reported. A vitreous carbon electrode was used for the (437) and Vitamin B (376) were examined by a n ac methdetermination of 4-aminophenol in dosage form (994). Oxod. Polarographic data for metal complexes of thiouracils idation a t a tubular carbon electrode was used for Dopa were correlated to structure and biological activities (357). analysis (738). Pulse and dc methods were used for the Polarographic kinetic currents were reported for 2-keto-1determination of disulfiram in tablets a t a rotating glassy gulonic acid (1120). graphite electrode (912). Polarographic data were reported for human methemoAnalytical procedures were reported for sodium phenyl globin (91, 522), native horse heart cytochrome C (92, 93), dimethylpyazolonemethylaminomethanesulfonate (944), and for ferredoxin from clostridium pasteurianum (1179). menadione sodium bisulfite (745), 2-phenylindan-1,3Oxyhemoglobin dissociation curves in blood were deterdione in serum (519), flurandrenolone in ointments and mined polarographically (369, 768). Prothrombin (blood creams (442), A*-3-oxo-steroids after TLC (424), 1-hydracoagulation factor 11) and thrombin (its product in the zinophthalazine hydrochloride and 1,4-dihydrazinephthalacoagulation sequence) were studied by a cv method and zinc sulfate (776), Sinthrome in cadaver blood (327)’, paattempts were made to correlate the electrochemical data paverine after TLC (4.23, ethacrymic acid in tablets and intermediate steps to the blood coagulation reaction (206), and methyl esculetol and rutin (913). An automat(276, 921 ) . ed polarographic analysis (60 samples/hour) was deProcedures for the polarographic determination of riscribed for 4-methylesculetin and rutin (62). boflavine in fermentation broths ( I I ) , urea in process Trimethoprim and its N-oxide metabolites in blood and streams (103), activity of BCG Vaccine (1157), of cateurine (136, 137), glibornuride in blood (249), and phenolcholamines in biological tissue (148), amino acid-p-nibarbital and diphenylhydantoin in blood after nitration troanilides (190), biotin (987) and some of its intermedi(138) were determined by pulse polarography. An ac techates (251), oxygen in blood (370), d-glucuronolactone nique was used for the analysis of urinary excretion of me(1078), and pectins (1014) were reported. The charge and tabolites of ethionamide and prothionamide (105). Twelve presence of active groups on the surface of whole sperm different pharmaceutical amines in tablets were detercells were detected (1144). Reduction data were reported mined after conversion to the amine oxide (455). An autofor Vitamin K3 in neutral and acidic media (180). Limitmated dc and ac polarograph using a DME was tested for ing currents and diffusion constants were determined for quality control with sulphenazone (201). A silicone rubber chromophor dextrans (82). based graphite electrode was used for the polarographic Pharmaceutical Compounds. Polarographic data were determination of phenothiazine, aminopyrine, phenacetin, reported for l-styryl-3,4-dihydroisoquinolines (253), 3-(5and others (917). m e t h y l - l , 3 , 4 -thiadiazol-2-yl thiomethy1)-7-[(2-(3-sydnone)acetamido)]-3-cephem-4-carboxylicacid sodium salt OXYGEN AND SULFUR HETEROCYCLIC (426), propipocaine and its unsaturated cleavage product COMPOUNDS p-propoxyphenyl vinyl ketone (433), for the anticoagulant Diphenylene dioxide (182) and benzofuroxan (1082) agent 3,3’-methylene-bis-(4-hydroxycoumarine)(dicouwere studied in aqueous and nonaqueous media. Griseomarol) (501), indomethacin (565), 11-epi cortisol and hydrocortisone (6201, streptomycin (999), and bovoside A fulvin was determined polarographically (1128). 4,g-Diphe(1170). 1-Hydrazinophthalazine and N1-carboethoxy-Nznyl-2-pyrone was examined polarographically in ESR hydrazinophthalazine (194, 371) and progesterone pyrrolstudies (213). A N A L Y T I C A L C H E M I S T R Y , VOL. 46, NO. 5, A P R I L 1974

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Data for 2-chloro-ethylthio esters of aromatic and furancarboxylic acid derivatives were reported as a function of pH and correlated to u constants (1124). Lowest vacant molecular orbital energies and reduction data were correlated for 4- and S-substituted benzofurans (314) and for oxonin, thionin, selenin, and 2,7-diaminophenazine (also UV absorption) derivatives (603). Tetrathiotetracene (359), 2,3,7,8-tetramethoxythianthrene (373), thianthrene cation radical ( # I ) , dibenzothiophen in HzS04 solution (4721, and 3,5-diphenyl-1,2thiolylium ion (72, 866, 868) were studied by cv methods. Carbonyl reduction in thiacyclanone-1,l-dioxidewas studied (929). Polarographic data were reported for cyclohepta[b or clthiophenones, H-cyclohepta[b or clthiophenes, cyclohepta[c or blthiophenylium salts, and thiophenic metallocenes (416), thioxanthene (583, 584), and 1,2- and 1,3-dithiolium cations (306). 1,l-Dithiolates and their Hg complexes (116) and 1,3-dithiole derivatives (483) were studied by ac and dc methods. Three anodic steps a t Pt were reported for dibenzothiophene (120). Reduction of trithiapentalene derivatives and oxidation of its dication dimers was described (867). The effect of adsorption was noted in a study of the methyl ester of 5-chloro-2-thiophenecarboxylicacid (755). Thiophanate residues in vegetables were determined by an op method (736).

Polarographic data were reported for acridine, 9-aminoacridine, and its dimethylaminoalkyl derivative (196) and mononitro (199), trinitro (195), and halogen (198) derivatives of 9-dimethylaminoalkylaminoacridine. Dimethylbiacridinium ion (674) and acridizinium ion (1104) were studied by a cv method. Diquaternary salts of 2-(2-pyridyl)quinoline ( I @ ) , quaternary salts of isoquinoline (1009), and 5 different quinoline and quinoxaline derivatives (958) were studied polarographically. The effect of substituent and pH was noted in an examination of 8-hydroxyquinoline derivatives (818). The catalytic wave for quinoline, quinine, and 3aminoquinoline was investigated as a function of pH (345). Polarographic data were reported for 3-iminoindolenine derivatives (21), 3-phenyliminooxindoles (614), and for azaindole derivatives (839). The reduction path and the effect of pH was described for 3-diazooxindole (169). Tetra(p-chlorophenyl)2,3,4,5-pyrrole and 2,3,4,5-tetratolylpyrrole (683, 684) were studied by cv methods. The effect of oxygen on the polarographic behavior of 5-amyl-2-pyrrolidinone was described (1215). Two oxidation waves in MeCN and one in MeOH and EtOH were found for 2,3,4,5-tetraphenylpyrrole(685). The reaction between 2chloromethyl-3-acetyl-4-methyl-5-carbethoxypyrrole with 2,4-dimethyl-3-ethylpyrrole was followed polarographically (564). Hammett a-Ellz correlations were found for substituted dipyrrolylmethene hydrobromide (747) and 2,5-substituted tetraphenylpyrrole (1001) derivatives. The effect of substituent on the oxidation of N-hydroxypyrrole was noted (179). The effect of pH and the reduction path was reported for 2-hydroxyimino-l,2-dihydropyrrolizin-l-one

NITROGEN HETEROCYCLIC COMPOUNDS Heterocyclic Compounds with One Nitrogen. Polarographic data were reported for isomeric imidazopyridinium salts (295, 689), N-substituted derivatives of nicotin(168). amide (562), 2-methyl-3-nitro-4-methoxymethyl-5-cyano- Polarographic data were reported for several substituted 6-chloropyridine (655, 698), 2-nitraminopyridine, . pyriphthalazines and corresponding dihydrophthalazines dine-2-isodiazotate, and 1-aminopyridinium iodide (702), (701), mono-, di-, and tri-benzomethoxyazocines (850), 19 mono- and disubstituted pyridinium iodides (712), and and a-enamines(piperidine) of lactams (893). Hammett oxidation data for 30 simple and 11 condensed 3,5-diacylu-E1,2 correlations were reported for substituted heterocyand 3,5-dicyano-1,4-dihydropyridines(1037). The oxidaclic N-oxide (773), biphenazinyl-2,2’ (382), and l-methyltion products of pyridine derivatives with the hydrazide 2-( 2’,2’-disubstituted-methylidene)hexahydroazepine function were determined polarographically (871). (892) derivatives. Correlation of Ell2 and nitrogen libraStyrylpyridine derivatives (12, 13). 1,2-bis(N-methyl-4- tion rate in the Dumas method was found for nitrogen pyridiniumy1)ethylene tetrafluoroborate (435), and 8-tertheterocyclics (756). butyl-l-(2-pyridyl)naphthalene derivatives (903) were Nitrogen-Oxygen Heterocyclic Compounds. Voltamstudied by a cv method. The effect of gelatin on wave metric data were reported for thianthrene-2,5-diphenylheights for the catalytic H-wave for pyridine (717), of 1,3,4-oxadiazole in an electrochemiluminescence study acidity on reduction of pyridine dicarboxylic acid (1090), (568). Diary1 derivatives of 1,3-oxazole and 1,3,4-oxadiaof adsorption on the reduction of N-alkyl pyridinium iozole (997), reduction of 0 - and S-substituted 2-hydroxy dide derivatives (1165), and of NH4+ on the behavior of and 2-mercaptobenzoxazoles (1052), oxidation and adsorppyridine carboxylic acid, nitriles, and amides (986) was tion of benzoxazolinethione (1053), and benzo-2,1,3-thia, noted. selena, and oxidiazoles in the presence of metal ions An ECE mechanism and data as a function of pH were (1115)were studied polarographically. reported for meso-tetra(4-N-methy1pyridyl)tetraiodide Polarographic data were reported for a series of R-sub(812). Radical anions of pyridine, pyrazine, pyridazine, stituted derivatives of X (383), heterocyclic substituted and pyrimidine were generated polarographically in an ethylenes XI (485), and for derivatives of XI1 (486). ESR study (604). Electron affinities for N-heterocyclics Me such as pyridinium and isoquinolinium ions were deterN 2 I mined (577). HMO calculated energy-El,~ correlations were reported for methyl substituted N-ethylpyridinium ions (792) and for isomeric cyanopyridines (1166). Substituent constants were used in correlations with Eli2 values for substituted pyridines, nitropyridines, and phenylazopyridines ( I 100). X Me Charge transfer energies [toward ( N H ~ ) ~ R uand ~ + lowest ] X = 0,8 Se K* energies were related to Ell2 data for several pyridine XI derivatives (669). Correlations between spectroscopic beX = 0, S, NMe havior of substituted pyridines and E1/2 values were considered (694). Effect of substituents at the heteroatom was noted in reduction of pyridinium cations (894). An op technique was used to study dipicolinic acid (160) and to determine the products of the oxidative ammonolysis of 2-picoline (450). Picolinealdehyde, picolinic XI1 acid, picolinamide, and picolinonitrile were determined X =0,N; Se polarographically (985). Substituted 2,2’-dipyridyl N-oxides were studied as a function of pH (561). The adsorption of 2,2’-dipyridyl on The effect of the proton donor hydroquinone on the reducHg (798), reduction of 4,4’-bipyridyl (1167), and determition of several phenyl- and naphthyl-substituted oxazoles nation of 4,4‘-bipyridyl and its mono and bisquaternary and ozadiazoles was described (1020). salts (995) by polarography were reported. .Diquaternary Aggregation effects of polymethine dyes were studied salts of bipyridyls and dipyridyl ethylenes were studied by polarographically (412). A Pt mesh electrode was tested as ac and dc methods (482). a reference electrode by using polymethine dyes as a

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model compound (516). Eight derivatives of benzo(a)phenoxazine were determined by an op technique (617). The stability of naphthalene 2,2’-pphenylene bis(5phenyloxazole) toward gamma radiation was polarographically determined (727). Half-wave potentials for 23 oxazolium, thiazolium, selenazolium, and imidazolium ions were calculated by Pariser-Parr-Pople method (326). A correlation between E112 values for 2,3-dimethylbenzoxazolium, 2,3-dimethylbenzothiazolium, and 2,3-dimethylbenzoselenazolium derivatives and energies for the first empty MO was reported (325). Polarographic data for 23 sydnones and sydnonimines were related to dipole moments, absorption frequencies, and other observable molecular parameters (123). Correlations were found for Ell2-spectral data for polymethine dyes of the type benz-, imida-, thia-, oxa-, and selenacarbocyanines (413). Nitrogen-Sulfur Heterocyclic Compounds. Polarographic data were reported for 1,2-benzoisothiazole derivatives (935), 2,1,3-thia and selenadiazoles (1116), and thiazolidine derivatives as a function of pH (1033, 1058, 1059). Thiazolium salts (535), 2,2’-benzothiazolinene azine (525), and 2-substituted 3~methylbenzothiazolium salts (797) were studied in detail. The electrode mechanism was elucidated for 2-mercaptothiazoline as a function of pH (58). Polarographic data (937) and the determination (984) of methylene blue were reported. The phenothiazine-oxygen molecular complex (888) and phenothiazine and N-substituted compounds (278) were determined polarographically. Reduction data for N-substituted phenothiazines were studied in H2S04 solution (884). Energies for highest occupied orbital were correlated to polarographic data for phenothiazines, nitriles, and nitro compounds (622). Heterocyclic Compounds with Two o r More Nitrogens. Detailed electrochemical data were reported for 6methoxy-1-phenazinol-5,lO-dioxideas a function of pH (260) henazine, 3-methyllumiflavine, and riboflavine (602): p1enazine as a function of solvent and acidity (965) and for mono- and di-N-oxides of phenazine, quinoxaline and benzo[b]phenazine (1048). The reduction pathway and effect of cations was described in a study of phenazine, riboflavin, and 3-methyllumiflavin (966). Data for 2-substituted phenazines were correlated to u values (794). Jaffe u constants and energies for lowest free MO were correlated to Ellz data for a- and p-substituted phenazines (381). Halogenated ( 7 ) and other substituted (671) 2,6-naphthyridine derivatives were studied as a function of pH. The dc results for 1,4-benzodiazepines (204) and the effect of acidity (205) were described. Quinoxaline and its 2- and 2,3-alkyl substituted derivatives (316), its N-oxide derivatives (576), and its substituted 2-carboxylic acid derivatives (281) were studied polarographically. Detailed data were reported for 6-pyridazinone and derivatives (374), pyridazine (591), furo[2,3dlpyridazine (227), arylpyrazolines (1017 ) , and for l-phenyl-3-methyl-2-pyrazoline-4,5-dione and rubazonic acid in ESR studies (1129). Salazopyridazine was determined polarographically (735). Three reduction waves as a function of pH were reported for p.yrazine (590, 943). Several pyrazine derivaLITERATURE CITED Agaev. U. K.. Mekhtiev, S. D., Mekhtieva. 2 . H.. Srnirnova. V. P., Rizaeva, S. Z . , Azerb. Khim. Zh., 1971, 26. Agarwal, H. P.. Bhargava, M.. lndian J . Chem., 9 , 1379 (1971). Albisson. A . , Sirnonet, J., Bull. SOC. Chim. F r . , 1971, 4213. Albota. L. A., Rudi, V P., Albota, N. K., Grishina, M. G . , Ukr. Khim Zh., 38, 1001 (1972). Aleskovskii. V. B., Lapitskaya, S. K., Sviridenko, V. G., lzv. Vyssh. Ucheb. Zaved., Khim. Khim. Tekhnoi., 15, 499 (1972). Alexander, P. W . , J. Electrochem. SOC., 36, App. 21 (1972). Alhaique, F..Riccieri, F. M., Carnpanella, L.. Ann. Chim. (Rome), 62, 239 (1972).

tives (36) and dihydro-5,6-pyrazines and a-diimines (8863 were studied as a function of pH. Electrochemical studies were reported for 1,2,3,4,5-pentaarylimidazolium cations (443) and for the imidazole(NC)zC=C(CN)2 charge transfer complex (830). Oxidation data for triarylimidazole derivatives were correlated to u values (1OOO). Energies for highest occupied MO and K D values for imidazol4.5-hlauinolines were found to be .rd&ed (445). 1.10-Phenanthroline was studied bv dc methods (121). while ac and dc methods were used-for quaternary’salts derived from phenanthrolines, 2,7-diazapyrene, and diazoniapentaphenes (481).Half-wave potentials for ferroin and cuproine type ligands were correlated to adsorption spectral data and energies for lowest unoccupied ligand MO .

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(411, 444).

Polarographic data were reported for 7 different heterocyclic azines such as 1,3-dimethyl-2-benzimidazolinone azine (484),azopyrazolone derivatives (899), quaternary salts of purines (1085), bisquaternary perchlorates of substituted 1,7- and 4,lO-diazachrysene (1086) and for 6chloro-7-azaindoline (1190). Benzofuroxan (1083), 5-phenyl and 1,5-diphenyl-3-styrylpyrazole(407), and 2,4- and 2-methylcinnolinium iodide (489) were studied by cv methods. The reduction path for 4-substituted quinazolines and 6-substituted purines was described (652). Electrochemical data were’ described for aromatic and quinoid pteridines and 7,8-dihydropterines (129) and 4(3X)-pteridones (650). The oxidation of several tetrahydropterins by Fe3+ was followed polarographically (32). Polarographic investigations of melamine (1213), asymtriazine-3-one or thione as a function of pH (887), and tetraazapyrene and its N-oxide (88) were reported. Phthalo-

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S03H

x1n were studied by an ac technique. The oxidation of persantine was described (656). Voltammetric data were reported for tetraphenylporphine (543) and a, (3, y, 6-tetraphenylporphin in electrochemiluminescence studies (1098). The reduction of mesotetra-2-pyridylphorphine and 3-pyridylphorphine was investigated by dc and cv methods (810, 811). Donor-acceptor properties and correlation to 0 values was reported in a polarographic study of triphenyl verdazyl derivatives (898). A circuit design for a programer for cv was described and tested with xanthine (709). 2-(2’Hydroxy-5’-methylphenyl)benzotriazole(96) and triazine herbicides (711) were determined polarographically. ACKNOWLEDGMENT The author thanks Sherlock Swann, Jr., and Stanley Wawzonek for their valuable assistance in scanning Chemical Abstracts.

( 8 ) Allcock, H. R., Birdsall, W. J . , Inorg. Chem., IO, 2495 (1971). (9) Allen, P. C.. J. Ass. Oftic. Anal. Chem., 55, 743 (1972) (10) Alt. H.. Binder. H., Klernpert, G.. Koehling. A.. Sandstede, G., J. Appl. Electrochem., 2, 193 (1972). (11) Altmark, E.. deDardik, C. A,, SOC. Argent. Farm. Bioquirn. ind., 12, 663 (1972). (12) Alwair, K., Archer, J. F . , Grirnshaw, J.. J . Chem. Soc., Perkin Trans. 2, 1972, 1663. (13) Alwair. K . , Grirnshaw. J., J. Chem. SOC., Perkin Trans. 2. 1973, 1150. (14) Amore, F. J.. Diss. Abstr., 3 2 8 , 4456 (1972). (15) Anderson, L. B.. Broadhurst, M. J.. Paquette. L. A.. J. Amer. Chem. SOC., 95, 2198 (1973).

(16) Anderson, L. B.. Paquette. L. A , !bid., 94, 4915 (1972). (17) Andrieux. C. P., Lamy, E., Nadjo, L., Saveant. J. M., J. Electroanal. chem., 42, 189. 221 (1973). (18) Andrieux, C. P., Saveant, J. M . , ibid.. 33, 453 (1971). (19) Andrieux. C. P.. Saveant, J. M . , BUM SOC. Chim. Fr., 1972, 3281. (20) Andruzzi, R . , Cardinali, M. E., Carelli, I , , Trazza, A., Ann. Chlm. (Rome), 6 1 , 415 (1971). (21) Andruzzi, R.. Cardinali, M. E., Carelli, I . , Trazza, A.. J . Electroanal. Chem.. 36, 147 (1972). (22) Andruzzi. R . , Cardinali, M. E., Trazza, A,, €lectrochim. Acta, 17, 1524 (1972). (23) Andruzzi, R.. Cardinali, M. E.. Trazza, A,. J . Electroanai. Chem.. 41. 67 (1973) (24) /bid., p 429

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Chromatography Gunter Zweig Criteria and Evaluation Division, U.S. Environmental Protection Agency, Washington, D.C. 20460

Joseph Sherma Chemistry Department, Latayette College, Easton, Pa. 78042

In the period since our preparation of the last Chromatography review for this Fundamental Reviews issue, chromatography has remained a very widely used analytical technique, with over 8000 publications on all aspects of chromatography appearing in the world literature. This review covers the literature of liquid column chromatography, paper chromatography, and thin layer chromatography (excluding ion exchange, which is reviewed separately elsewhere in this issue). The authors have attempted to select the most important publications abstracted in Chemical Abstracts between December 20, 1971, and December 3, 1973, and when possible, papers were selected which were published in journals readily accessible to American scientists. In order to conserve space and prevent possible overlap with coverage in the Analytical Applications Reviews published by this Journal in alternate years, the extensive second section on “Applications of Chromatography’’ ar-

ranged according to compound types, which has traditionally appeared in this review, has been eliminated. Some selected applications of the various chromatographic methods are still mentioned below, however, under the appropriate headings. During the past two years, the American Chemical Society sponsored short courses on modern liquid chromatography and maintaining and troubleshooting chromatographic systems. The Chemical Rubber Co. two-volume “Handbook of Chromatography,’’ edited by Zweig and Sherma, and a book presenting a unified introduction to separation science by Karger, Snyder. and Horvath (Wiley-Interscience) were published, and a new supplement to the Journal Separation Science entitled Separation and Purification Methods (Dekker) appeared. Preston Technical Abstracts Co. introduced a service providing regular abstracts of the LC literature, and Sadtler offered an audio-visual teaching program on LC. An Institute for A N A L Y T I C A L C H E M I S T R Y , VOL. 46,

NO. 5,

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