Chromatography - Analytical Chemistry (ACS Publications)


Chromatography - Analytical Chemistry (ACS Publications)https://pubs.acs.org/doi/abs/10.1021/ac60185a002Cachedby E Heftm...

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(354) Tsen, C. C., ANAL. CHEM.33, 849 (1961). (355) Turba, F., Heimberger, N., Biochem. Z. 330,359 (1958). (356) Turunen, L., ASAL. CHEY. 33, 1617 (1961). (357) Ungnade, H. E., ed;,, “Organic

Electronic Spectra Data, Vol. 11, 1953-1955, Interscience, S e w York, 1960.

(3587 Uriel, J., Gotz, H., Grabar, P., Schwezz. med. Wochschr. Supp. 14, 431 (1957). (359) Uskert, A., Ann. 638,199 (1960). (360) Vaintraub. A.. Biokhimiua 25. 688 (1960). (361) Vandenheuvel, F. A., Sipos, J. C., ANAL.CHEM.33,286 (1961). (362) Vanden Heuvel, W.J. A., Haahti, I

.

E. 1’.A., Horning, E. C., J . Am. (’hem.

SOC.83,1513 (1961). (363) Vanden Heuvel,

W.J. A., Horning, E. C.. Biochem. Btowhus. Research Conzmuns. 3 , 3 5 6 (1960): (364) IEid., 4 , 3 9 9 (1961). (365) Vanden Heuvel, W. J. A., Sidvall, J., Horning. E. C., Biochim. Biophys. Acta 48,596 (1961). (366) Vanden Heuvrl, W.J. .4., Sweeley, C. C., Horning, E. C., Bzochem. Biophys. Resparch Corrimuns. 3 , 3 3 (1960). (367) VanSlyke, D. D , Plazin, J., J . Bid. C h e m 235,2749 (1960). (368) Vestling, C. S.,ed., “Biochemical

Preparations,” Vol. 6 , Wiley, New York 1958. (369) Vigneron, M.,Ann. pharm. franc. 18,404 (1960).

(370) Vorbeck, M. L., Mattirk, L. R., Lee, F. A., Pederson, C. S., AXAL. CHEM.33,1512 (lY61). (371) Wade, M. A., Seim, H. J., Ibid., p 793. (372) Wadsworth, bI. E , “Physical Methods in Chemical Analysis,” Berl, W.G., ed., 1701. 4 , pp. 99-117, Academic Press, Xew York, lY61. (373) Wagner, H., Horhammer, L., Wolff, P., Bzochem. Z. 334,175 (1961). (374) Warburg, O., Xruppahl, G., Z. A’aturforsch. 15b, 364 (1960). (375) Wawszkiewicz, E. J., ANAL.CHEM. 33,252 (1961). (376) Wawzonek, S., I b z d , 32, 144R (1960).

(377) Weinberg, D. I., IRE. Intern. Conv. Record. 8 , Pt. 9, 88 (1960). (378) Weiss, H. V., Lai, ill.G., .\NAL. CHEV.33,39 (1961). (379) Weissberger, A., ed , “Physical Methods of Organic Chemistry,” 2nd ed., Interscience, S e w York, 19491962. (380) Weisz, H., “Microanalvsis by the

Ring Oven Technique,” Pergamon Press, Kew York, 1961. (381) Weller, C., Linder, M., Nacaulay,

A., Ferrari, A,, Kessler, G., Ann. N . Y. Acad. Scz. 87,658 (1960). (382) Wieme, R. J., “Studies on Agar Gel Electrophoresis,” Orscia Uitgaven, N. V., Brussels, 1959. (383) Killard, H. H., Merritt, L. L., Jr., Dean, J. A., “Instrumental Methods of Analysis,” 3rd ed., Van Nostrand, Princeton, N. J., 1958. (384) Williams, K. T., Wilson, J. R., ANALCHEM.3 3 , 2 4 4 (1961). (385) Willis, J. B., Ibzd., p. 556. (386) Winefordner, J. A., Late, H. W., Ibid., p. 1727. (387) Witmer, F. J., Austin, J. H., illikrochim. Acta 1960, 502. (388) Wollish, E. G., Schmall, M., Hawrylyshyn, M.,ANAL. CHEM. 33, 1138 (1961). (389) M700ds, IC R., Engle, R. L , Jr., Ann. A’. Y. Acad. Sci. 87, 764 (1960). (390) Wotiz, H. H., Martin, H. F., J . Bid. Chem. 236, 1312 (1961). (391) Yphantis, 1).A., Ann. A’. Y. Acad. Sci. 88, 586 (1960). (392) Zak, B., Cohen, J., Clin. Chim. Acta 6 , 6 6 5 (1961). (393) Ziffer, H., Vanden Heuvel, TV. J.

A., Haahti, E. 0. A., Horning, E. C., J . Am. Chem. SOC.82, 6411 (1960). (394) Zilversniit, D. B., ed., J . Lipid Research 1, KO. 1, Lipid Research, Inc., Memphis, Tenn., 1959.

Review of Fundamental Developments in Analysis

Chromatography Erich Heftmann, National Institutes of Healfh, Bethesda, Md.

T

review covers the period since Strain’s last review in 1960 (1143) and includes only the articles which have come to the author’s attention before December 1981, exclusive of routine applications of known methods. HIS

LITERATURE

Except for the book by Martin and James (726), all current monographs on the general topic of chromatography (209, 3213, 467, 660, 1097) have been written, characteristically, by more than two authors. This also applies to a comprehensive treatise on paper chromatography (437). I n addition to these books, a number of review articles on chromatography in general have been published in the last 2 years (222, 2613, 419, 4713, 641, 765, 769, 1070, 1143-5, 1270). R e v i e w of more limited scope have dealt with such topics as the separation of stereoisomers (522) and radioactive compounds (977), or the application of chromatography to clinical analysis ( 4 l 8 ) , or t o genetics and taxonomy (165). Other reviews will be cited under specific headings.

HISTORY

The history of chromatography has been outlined by Zechmeister (1303), and Grune (416) has written about capillary analysis, a predecessor of paper chromatography. A biographical sketch of Tswett has also been published (976). It should be recorded here t h a t the first and second Labline Awards in Chromatography and Electrophoresis have gone to Strain (204) and Zech-

meister ( I 4 ) , respectively. Both men have made outstanding contributions t o our knovledge of chloroplast pigments by the judicious application of Tswett’s method. THEORY

Giddings has been considering kinetic processes in chromatography (381, 674) with special emphasis on zone diffusion (580) (cf. also 113, 581, 605). Corrections for oyerlap in elution curves

Chromatography The rapid growth in various aspects of chromatography has been evident for the past several years. This, in turn, has presented problems in preparing reviews in this field. In 1960 the editors presented two reviews: chromatography b y Harold H. Strain and gas chromatography by Stephen Dal Nogare. In 1962, on the basis of discussions with experts in the field, it was decided to break the topic down as follows: chromatography (except electro, gas, and ion exchange chromatography), electrochromatography, gas chromatography, and ion exchange chromatography. The authors are: Erich Heftmann whose chromatography review covers solid-solid adsorption, liquid-liquid partition, Molecular Sieve processes, etc. R. P. Strickland has prepared the review on electrochromatography; Stephen Dal Nogare, gas chromatography; and Robert Kunin, ion exchange chromatography.

VOL. 34, NO. 5, APRIL 1962

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have been calculated (1306), and equilibrium theory equations for column chromatography have been developed (396). Adsorption. T h e theoretical basis of adsorption chromatography has been discussed by several authors (62, 125, 18.4,211, 385, 434). Much attention has been given to the properties of adsorbents (296, 933) and to the determinatioii of hcats of sorption (414, 483, 588, 809, 1030, 1092, 1192, 1240) and of isotherms (361, 418, 431, 589, 602, 908,910) to elucidate the mechanism of adsorption (386, 387, 501,1090, 1091). SYhile the majority of the investigators h a r e focused their attention on the three most commonly used adsorbents, charcoal (93, 326, 370, 371 390, 519, 1012, 1267), alumina (202, 429, 697, 699, 626, legs), and silica (299, 484,690, 596, 611, 774, 821, 897, 1141, 1293), some studies have also been reported on magnesia (1221), molybdic oxide (f064),cracking catalysts (86),aluminosilicates (346, 685), hydroxyapatite (276), and a number of natural adsorbents (64, 166, 167, 1076, 1219, 1296, 1300). Interesting adsorptive properties are exhibited by specific silica gels (807) and by silica gels modified by methoxylation (208) or by dimethyldichlorosilane (808). Polyamide columns (487)sorb various organic molecules partly by formation of hydrogen bridges and partly by dipole interactions (294). The use of various polymers in chromatography is suniinarized inarecent book (1128). Stereosrlective inorganic adsorbents are capable of resolving complex optical antipodes (76,310,598). Theoretical studies of adsorption directly related to chromatography include RachinskiI's analysis of sorption dynamics (945, 946) (cf. also 304, 427, 1190) and Snyder's linear elution adsorption chromatography (1103)i t . , elution chromatography n ith linear adsorption isotherms. The theoretical plate concept has been applied to columns with tiyo or more layers of different adsorbents (1002), and complex formation of migrants with eluents has been discussed (363). The role of paper in paper chromatography has b w n discussed by Peril& (883) and by Grune (416) (cf. also 622). In the separation of inorganic ion. some of the underlying mechanisms niay be similar to salting out (970) or precipitation (462, 516, 643, 728, 740, 913, 993), although partition mechanisms have also been invoked (333,1286). The electrolyte solutions used as developers niay affect chroniatographically important properties of paper, and R values decrease exponentially n i t h a n increase in electrolyte concentration (524). When organic solvents are used as developers, the R

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values of inorganic ions increase linearly mith the dielectric constants of the solvents (378). A method for determining the optimum n ater and acid concentration in solvcnt systems for inorganic scparations has been described (186), and in buffered-paper chromatography, the pH for optimum resolution of organic electrolytes can be d c u l a t e d (1104, 1246). Eiidence has been presented that chromatographic separations on impregnated glass-fiber paper may be based on partition if phosphate buffer is used, but on adsorption if it is impregnated ith silicic acid (529). Partition. T h e theoretical basis of partition chromatography is thoroughly discussed in two review chapters (126, 382). The imbibition (128, 456) and flow (128, 199,994, 995) of solvents in filter paper arid their significance have been critically examined, and the influence of the shape of the paper (352) and of acceleration of flon by centrifugal force (243) have been analyzed. There have also been discussions on the formation of multiple spots (78, 573) and residual spots a t the origin (199) in paper chromatography. h number of publications have dealt with the theoretical relations b e t w c n 01, Rr, and R.u (383, 404, 656). Only some examples of the correlation between structure and chromatographic behavior of migrants nil1 be cited here (61, 73, 336, 496, 576, 693), sinre others are given in thr sectioiis on specific applications. Sources of error in the determination of Rp valucs have been discussed (907). Molecular Sieves. This topic has recently been reviewed by Barrer (H), Flodin and Porath (326)) and Hersh (477). Molecular Sieves have several theoretically interesting (89) and chroniatogra~)hi~all~useful (323, ) properties, 1s will be evident from a perusal of later sections. TECHNIQUES A N D APPARATUS

General. Technical aspects of adsorption chromatography ha\ e been summarized in chapters by Chovin (211) and by Hagdahl (4341. Thin-layer chromatography, unjustifiabl! iieglectrd for many years, has recently come into extensive use, and a large crop of review articles on this subject attests to its present popularity (46, 2.5Yl 813, 1039, 1118, 1229, 1241, 1277). The techniques of liquid-liquid partition chromatography have recently been reliened (126, 533, 694) and a small volume on the practical aspects of paper chromatography has just appeared (674). More limited discussions of paper chromatography deal n ith such subjects as radial (4.94, 896) and centrifugally accelerated ( 1169) development or quantitative (784, 1171) and radiochemical (914) methods. Paper chromatography has great pos-

sibilities in systematic organic analysis (931, 938). Columns. Pelzer (878) has discussed nioderii apparat'us for chreniatography and electrochromatography, notably for colunin chromatography (401). Apparatus for column chromatography a t low temperatures has been described (500). A roll of filter paper (436) or a rectangular box, filled n-ith cellulose powder (441), may be used for preparative work. Standardization methods for alumina (640) and silica (474) have been described. dutoniatic devices for changing eluents (462, 630, 9-$4), as n-ell as valve dcsigns for the regulat'ion of flon. ratrs (531, 785, 810, 1040) have been published. The efficiency and convenience of gradient elution have made this technique one of the most valuable adjunct's to column chromatography, regardless of the sorpt'ion process selected (649, 754). Somograms have bwii present'ed (608, 1265) and calculations have been extended t o three-component elut'ing systems (846). A number of gradient elution devices have been described (15, 25, 31, S90, 971, 1282), including one for tandem operation (1227). Ailuxury only a few years ago, fraction collectors have now become almost indispensable equipment for coluniii chromatography. 1 variety of neiy designs have been published (41, 177, 738, 877, 924, 1161, 1189, 1275), including fraction collectors for tandem operation (1228) for work n-ith flainmable solvents (922) and for drying t'he fractions (1047), as ne11 as a simple siphon device (432). Nore sophisticated instruments divide the fractions into aliquots ($5, 971, 988, 1052) or determine their absorbance automatically (25, 971, 1202). Continuous analysis has been effect,ed by passing t'he effluent stream through, depending on the method of annlysis, quartz flow cells (16, 27, 81, 87),a rock salt cell ( l a u l ) , a titration cell (Sag), a refractometer (SSS), or a counting cell (105). Weak beta emitters are continuously monitored as they flow over scintillat'ors imbedded iii plastic (1089, 10.40). Sheets. Details of technique (1116) and apparatus (1277) for thin-layer chroiiiatography h a r e been described, including a method of quantitative eraluation from photoprints (466). Chromatography on porous glass plat'es (691, 692) appears to hold much promise, as glass is both resistant to most reagents and transparent; the surface may be modified by various cheiiiical treatments. Publications on technical iniprovenients of paper chromatography continue to take a large share of the chromatographic literature (446, 713, 815). Trace metal impurities may be re-

inoved from paper b y prewashing with E D T A (6, 730). Special shapes of filter paper include a funnel (428) and a circular, divided shc>et (906). A large variety of devices for sample application have been described (118, 246, 305, 362, 699), including a n automatic applicator (1297), a streaking gadget (1253), a spotting apparatus for large volumes (682),and a tube oven (101, 966) resembling a ring oven. Resolution is improved by chromatographing ring-shapc.d zones, rather than spots (1279). Before application, the sample should preferably be dissolved in the stationary solvent (1056). The word elatography has been coined for the procedure in nhich the sample is chemically transformed on the paper prior to development (74). Chromatography jars inay be improvised from glass building blocks (612), and they may be designed for preliminary equilibration with the vapor phase (932) or for chromatography in a n inert atmosphere (1164). The developers inay be delivered from homem o d solvent troughs (969), slit-feeding troughs (165), or even plastic bags (426). Timers t h a t start the development automatically (5, 1216) are convenient for those a w k n s r d developing periods between 8 and 15 hours. Several new techniques of radial development have been recommended (216, 359, 632), such as vertical circular chromatography (391) and a semicircle method (1164). To save time, a zone from one chromatogram may be eluted directly onto a radial chromatogram (695). Improved methods for centrifugal acceleration of radial development have also been described (243, 744, 1177). -1 method for t h e comparison of two solutions on a single paper strip has been patented (1166). There have also been some improvements in horizontal (1021) and multiple two-dimensional paper chromatography (1257). Several dyes make suitable markers for t h e solvent front (1109). *Ipparatus has been described for the drying of paper strips (394), for the alqdication of detcction reagents (499, 1133), including a variety of sprayers (123, 668, 964, 1659), and for heating sheets on a glass plate (847). Blake has perfected a n electrostatic discharge (106) and a rectified low-frequency (107) method of zone location. P a n (869)reported a n iniproved detection method Tvith iodine vapor. M a n y organic substances give fluorescent spots n ith quinine sulfate or sulfosalicylic acid (982). Ultraviolet-absorbing materials can be photographed through a fluorescent intensification screen (889). An elastic scale may be used for rapid determination of Rp values (1054). Chromatographic spectra (339)are plots of R F values in a fixed sequence

of solvents, which aid in the identification of compounds a n d may give clues on structural details. Paper chromatograms m a y be quantitatively evaluated by spot area estimation (607) after preparation of a color slide (440) or contact print (2, 502). Reflectance measurements (536, 1162), photoelectric determination of fluorescent materials (49, 297, 408, 1313) or transmission photometry (234, 685, 736) may be used. =Inalog integration techniques are applicable to paper chromatograms (1149). Radioactive materials may be measured b y quantitative autoradiography (802) or by a variety of automatic scanners (179, 653, 276, 684, 787, 1223). Kindowless gas flow counters are used (85)and the paper may be counted from both sides (845,1264, b u t i t is also possible to record the photoemission of a halogen-filled Geiger tube on photographic film (53). There are even scanners for two-dimensional r a d i o c h r o m a t o g r a m s (340, 884). Labeled compounds on paper may also be detected by impregnating it r i t h a liquid scintillator (828) and exposing a photographic film to it (860, 1272) or by immersing i t directly in a scintillator solution (130, 1250). Sources of error in gas flow (97) and scintillation (681) counting of paper chromatograms have been discussed. If the determination is to be made o n eluted material, there is a wide choice of elution devices (54, 146, 176, 998, 1089), even a fraction collector for strip chromatograms (3). A technique for obtaining infrared spectra of eluates from paper chromatograms has recently been published (272). APPLICATIONS

Inorganic Ions. F o r t h e chromatographic separation of inorganic ions, columns of alumina (36, 280, 582, 836, 1198), silica gel (133, 733, 902, 1153, 1249), cellulose (22, 99, 319, 332, 377, 843, 861), or specially prepared calcium sulfate sticks (1061) may be employed. Excellent results have been obtained by use of reversed-phase partition columns in which tri-n-butyl phosphate (312, 445, 1075) or tri-noctylphosphine oxide (267) forms t h e stationary phase. Successful separations have also been reported TT ith columns containing the complexing agents 8-quinolinol (628), dithizone (903), phenylarsonic acid (17), and rubeanic acid (399). Precipitation chromatography (439, 616) and diffusion-precipitation chromatography on agar gel columns (834,1111),a n d oxidation chromatography on columns of oxidizing or reducing agents (836) have been proposed. Strips of dyed viscose rayon fabric separate small amounts of SrQO,Zn65, and Ca4j (1173), and for

minute quantities of inorganic ions the use of threads has been suggested (706, 761). Glass-fiber paper has the advantage t h a t it can be used at 160' C. with fused salts (14) or fused benzoic acid (407) as eluents. A vast amount of literature on the paper chromatography of inorganic ions (664) attests to the usefulness of this approach. Comprehensive analytical schemes have been devised (291, 973). Frequently, tlerivatives, such as oxalates (1083, 1084), tartrates (1082, 1083), citrates (1083, 1085), thiocyanates (579, 1225), sulfides (961), 8-quinolinolates (629, 758, 795), thiourea (80, 665), nitrato (1245), or ammine and ethylenediammine (923), and chloro-complexes (79, 108) are chromatographed or paper impregnated with complexing agents is used (7, 517, 796, 797, 1046), but in other cases complex formation n ith the solvent systems may occur (1051, 1081). Typical developers contain water (960, loss),inorganic acids (10, 84, 168, 250, 287, 552, 838, 954, 966, 951, 1138, lass), bases (504, 727, 88R),and salts (15,242),often in the presence of organic solvents, such as butanol (60, 154, 216, 223, 252, 647, 663,860, 926,1036,1163), isopropanol (837), phmol (705), benzyl alcohol (1065), monoethyl Cellosolve (710), or tri-n-butyl phosphate (580, 1261). Continuous evaporation of the solvent may improve the fractionation (783). Some of the detecting reagents mentioned in recent publications are: dithizone ( 2 174, 1182), alizarin (9), diethyldithiocarbamate (876), chloranilic acid (66, 67), vanadylclinitrofluorone (for sexivalent tungsten) ( 7 1 l ) , resorcylaldehyde formylhydrazone (for scandium, gallium, and zirconium) ( @ I ) , pyrocatechol (for organotin compounds) (1271),tiron (for molybdenum) ( 1 1 ) , indicators (666, 667, 892), and basic dyes (for polyanionic compounds) (1080). X t r a t e may be detected by placing the paper on a film of diphenylbenzidine in concentrated sulfuric acid (680) or by spraying i t with a diazotizable amine and then a coupling reagent, after in situ reduction to nitrite by zinc powder (430). Nitrates, nitrites, and other nitrogenous compounds on filter paper turn brown 11hen exposed to radiation (13'1). The chromatography of esters of phosphoric acid, including the import a n t organic phosphates has h e n reviewed b y hlontreuil (780). Technical improvements in this field include the use of paper impregnated T$ ith quinoline molybdate (SO), the detection of phosphates b y radiochemical methods (968) and by molybdate, followed by a reducing agent (153, 983) or b y perchloric acid-molybdate and then benzoin (&is),and t h e trace analysis of phosphate mixtures (613, 687, 1256, 1269, VOL. 34, NO. 5, APRIL 1962

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raphy of uncombined aldehydes and ketones on filter paper (277, 470, 7 t 4 , 909, 1107) and silica gel strips (12, 56, 57, 353), and spot tests for naphthoquinones (1023) glyoxal (1024), and other aldehydes (69, 1026) have also been reported. Organic Acids. hsselineau (38) and Koda (819) have written summarics on the chroniatography of acids, and Fateeva (303) has reviewed their paper chromatography. Liquid-solid column chromatography is still used in this field; not only for carboxylic acids with additional functional groups (406, 526, 587, 729, 1206, t244) and sulfonic acids (515) or for a preliminary, crude separation (185,1010), but also for the fractionation of lower fatty acids (1203) and fatty esters (343, 421). F a t t y acids (566) and their esters (717) can be fractionated on undecane-impregnated (566) or nonimpregnated chromatoplates with results that are in some respects superior to those achievable by gas chromatography (717). For liquid-liquid column chromatography, silica is usually the carrier (321, 342, 342, 400. 768, 789.lo%), although for reversd-phase systrms polyethylene (886) or Celite-silicone (372) is a more appropriate packing material. For paper chromatography, filter paper impregnated with sodium molybdate, tungstate, vanadate, borate ( 4 4 2 , or polycaprolactam-formic acid (1252), or silica gel-impregnated glass-fiber paper has been recommended. Several new solvent systems (459, [email protected]), 830). including one containing indicators Alcohols. Review chapters are (&5), have been published. Reversedavailable on t h e chromatography of phase systems are almost invariably mono-, poly- (%5), and aminoalcohols used on paraffin-impregnated paper (541). Polyalcohols (75, 119), their (21, 82, 203, 301, 565, 1196, 1230). ethers and chlorohydrins (119), as The fattj- acids may be chromatowell as epoxy compounds (1027), have graphed as such, or in the form of their been separated by paper chromatogsodium salts (1049), 2,4-dinitrobenzyl raphy. For thin-layer chromatography esters (213), anilides (638), hydroxaon silica gel plates t h e alcohols were mates (1207),or methyl esters prepared first convcrtpd to p-hydroxybenzoates with CI4H2X2 (716). New detecting (358) or to 3,5-diiiitrobenzoates (67'5). reagents include mercurochrome (523) The latter are suitable derivatives for and diazotized p-nitroaniline (1268) for paper chromatography (366, 640, 753, the ammonium and chloranilic acid iZ98), but xanthates (365, 919)) urethans (562), nitrates (620), tosylates (66) for the sodium salts of organic acids, Turnbull's blue reagent (604), (590),p-nitrophenylazobenzoat es (124), a mixed indicator (864), and reagents and esters of azobenzene-4-carboxylic leading to the formation of Indanthrene acid (918) have also becn used. Blue (1037) and bismuth sulfide (1088). Carbonyl Compounds. This topic Minute quantities of organic acids may has been reviewed by Demole (256) and i t is also partly covered in van Duin's be detected by the electrometric conreview on liquid-liquid partition chrotact method (1502). A great variety of organic acids have matography of aliphatics (278). Mixtures of 2,4-dinitrophenylhydrazones been subjected to paper chromatography, e.g., dibasic acids (586, 724, have been resolved on adsorption (330, 829, 854; 1176), including phthalic 1276) and partition (227) columns, on acids (598);keto acids (37), including chromatoplatcs (262, 9&), and on filter aromatic pyruvic acids (10.48) ; various paper (8, 111, 663, 896, 1031, 1299). indole acids (420, 463-6, 514, 694, 660, Other derivatives of carbonyl com981, 1265) ; gibberellic acid (916 ) , pounds for use in paper chromatography cyanoacetic acid (1152); naphtholsulhave been prepared by condensation fonic acids (614, 646,1059); and aminowith maleic hydrazide (412) or cyanonaphtholsulfonic acids (367). acetohydrazide (337). Chromatog-

1278). Other interesting applications of paper chromatography to inorganic analysis that deserve special mention are: the separation of anions (318, 320, 518, 955), of alkali and alkaline earth metals (189, 584, 709, 891), of precious metals (657, 708), and of uranium (782,1053). I n addition to the conventional methods of evaluating paper chromatograms, such as visual comparison (7, 635, 814, 1006) or measurement of spot areas (71, 72, 636, 683), analysis after elution (59, 9.4, 642) or ashing (190, 279, 926, 1105) of t h e paper, or retention analysis (1287), a number of physical methods are applicable to inorganic ions-e.g., activation analysis (122), radio-frequency methods (148), potentiometry (393), x-ray fluorescence analysis (621), and beta-ray reflection (1191). Hydrocarbons. It is evident from recent reviens (91, 260) that gas chromatography is now the method of choice for the separation of hydrocarbons. However, there is still some research activity in the application of liquidsolid adsorption chromatography on columns, usually of silica gel or alumina (274, 490, 527, 621, 823, 880, 927, 936, 1025, 1102, 1112, 1226, 1966). Even paper chromatography on ordinary (669, 824, 894, 931, 1028), acetylated (753, 871, 11141, or benzoylated (752) cellulose paper is applicable to hydrocarbons. Molecular Sieves are used with low-boiling liquids as eluents (763,

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ANALYTICAL CHEMISTRY

~

Quantitative evaluation of paper chromatograms has been effected by planimetry (1093), photometry (1056, 1166), and by elution (164) after conversion to the copper salts (485), hydroxamates (438, 921), or, in the case of keto acids, to 2,4-dinitrophenylhydrazones (546,i304). Lipides. T h e entire field has been adequately reviewed (29, 39, 327, 786, 819, 1179), and reviews on paper (748) and column (449, 1281) chromatography are also available. For column chromatography, silicic acid is t h e adsorbent of choice (98, 112, 176, 235, 495, 678, 985, 999, 1004, 1006, 1050, 1078, 1233, 1281, 1283, 1289, l s l l ) , although some work on columns of alumina (219, 683, 1071, 1078) and of cellulose (220) also has been reported. For adsorption chromatography on sheets, silicic acid, again, is eminently suitable. Silica gel plates are used for thin-layer chromatography (712, 939, lZ43, 1260), and fiber-glass sheets (193, 194, 444, 791, 844) or filter paper (229, 433, 493, 747, 965, 966, 1307) impregnated with silicic acid for paper adsorption chromatography. Paper partition chromatography can be carried out either a i t h conventional solvent systems ( 3 6 4 , using formaldehyde-treated paper (489, 1242), or with reversed-phase systems (557), using paper imprrgnatcd n-ith paraffin (659), silicone oil (669), or undecane (560, 567). While plasmals separate best n hen converted to 2,4-dinitrophenylhydrazones prior to chromatography (572), serum lipides may be chromatographed on paper directly nithout solvent extraction (7'23). Kaufmann has saponified gylcerides and phosphatides (564,K l ) , reduced carbonyl groups (661), and hydrogenated unsaturated fatty acids (570, 571) directly on the filter paper. S e w detection methods have been published for diglycerides (217 ) and various phospholipidcs (47. 156, 492, 1148), including cerebrosides (f SQ), and for sphingosine (1003). Amino Acids and Peptides. T h e chromatographic analysis of amino acids a n d peptides has been revien ed recently (163, 542, 778, 904). Thinlayer (137, 793, 827) and glass-paper (34) chromatography are beginning to encroach upon the microanalysis of amino acids and peptides, once considered the exclusive domain of paper partition and electrochromatography. The ncn techniques are superior to the older ones for protein hydrolysates in that no deionization is required and for the 1l'-(2,4-dinitrophenyl) amino acids (138) and 3-phenyl-2-thiohydantoins (138, 206), which are strongly adsorbed to paper. Dinitrophenyl amino acids have also been shown to separate well on columns of powdered nylon (1139) or polycaprolactam (409).

Gel filtration, another n e w o m e r to the field, is still limited to crude fractionations of amino acids and peptides (373, 671 , 928, 929). However, there is still a considerable volume of new literature on partition chromatography. I t is carried out on columns of pondered cellulose (704) and silica gel (654)and on filter paper (103, 201,259,271 ,282, 670,741,805, 840, 841,951, 953,960,101 6,10741185,1188, 1209, 121 7 ) . Sovel fmtures include the direct application of acid protein hydrolyzates to the moistened paper, folloned by drying in a stream of hot air (513), successive solvent development of biological materials without the removal of salts or proteins (863), and desalting of paper chromatograms by cutting off the starting spot (673). The effvct of moisture on the mobility of amino acids ($48)and the effect of pH on double and triple zoning (410) have been investigated. Various nensolvent systems have been proposed (23, 205, 447, 77ci, 1239), also paper chromatography a t elevated temperatures (479, 1074) and the use of various dyes to ;cr\ e as I iGiblc tracers of amino acids (713). Among the detection methods reported, the follon ing deserve special mention: ninhydrin (18, 737, 996, 1034, 119.9, 12741, chlorine and otolidine ( 1033), 6-chlorornercuri-2-nitrophenol (for thiols) (13), isatin (116, 498), ch1or:imine-T and a diazo reaction (for aspartic acid) (1135),the Sakaguchi reaction (9C).impregnation of the paper 11 ith 1,2-naphthoquinoiie-4-sulfonate for intensifying the fluorescmce test (842), and detection by heating the paper to 200' C. (633). Paper chromatographic method> hni-e been used for the analysis p-aminoof cyclic imino acids (EX), isobutyric wid (375), t-caprolactam (P36), and some guanidine derivatives (104,376, 855). Progress in the paper chromatography of dinitrophenyl amino acids (703, 849, 881) and phenylthiohydantoin dcriJ atives (207, 1046, 1087) and inil)rol-cd quantitative mrthods of amino acid analyiis (314, 672, 746, 1200, 1238) hai-c lieen reported. Proteins. As recent review chapters (302, 643, 978) indicate, adsorption (150, 170, 745, 822, 934, 975, 1106, 1232) aiid partition (212) chromatography are not likely to become serious competitors of ion exchange and electroc1iromatogral)liy in the protein field. .I possible exception may be the lipoproteins (180, 586, 690),nhich are not so strongly adboi bed. Gel filtration methods (296, 383, 677, 686, 929, 1312), on the other hand, offer some exciting possibilities for the separation of proteins according to molecular size. Schramm and N o h r (777, [email protected]?) have described a n interesting purification method for neuraminidase, based on filtration through a column of

kieselguhr, stromata.

mixed

with

erythrocyte

glucose oxidase reagent (1009). Quantitative methods have been described, Amines. Dietrich (666) has written based on direct photometry (11.4, 692, a review chapter o n volatile amines 530) and elution after staining (766,767). and Justisz (541) one on aminoalcohols. Phenols. I n addition t o t h e reAromatic amines have been chromatov i e w by Dietrich ( 2 6 4 , Harborne graphed on reversed-phase partition (450),and Strachota (lid$?), there columns and, in the form of are also review articles (451, 857) on their azo derivatives, on adsorption the chromatography of a n especially columns (80.4).Paper chromatography interesting group of phenols, t h e has been used for aminoanthraquinones flavonoid pigments. Columns of mag(364), isomers of phenylenediamine nesia (803), Florisil (a%), and cellulose (345), 1,2-diphenyl-l-dimethylamino- (662, 812, 1237) are conventionally ethane (1290), allylamines (859), used for the fractionation of phenols, various onium compounds (788, 833), b u t the introduction of polyamide and pyridine bases (136, 619),for 2,4columns (244,369, 408, 488), eluted dinitrophenyl derivatives of amines with aqueous alcohol solutions, con(35), and for their X-alky1-3,5-dinitrostitutes a significant new advance in benzamides (121 8). this field. Polyamides may also be The chromatographie analysis of used in thin layers (289), particularly biogenic amines (42, 508, 1063) is in the form of polyamide-impregnated of great biochemical interest. Tissue filter paper (731, 1251). Other migra(1265) and urinary (794, 959) amines, tion media for sheet chromatography including catechol amines (395, 5 3 4 , are thin layers of silica gel (867), acetyhave been studied by paper chromatoglated (250, 486),and polyethyleneimine raphy. This technique has been very (752) cellulose paper. For convenvaluable in the analysis of various intional paper chromatography, eorrelatermediary metabolites of tryptophan tions between the structure of phenols (178, 550, 820, 940, 1115, l 2 3 l ) , of and their RF values have been studied choline and its esters (424, 664, 665), (288, 639, 963, 9S7), and effective as n ell as ethanolamines (338). solvent systems have been discovered Carbohydrates. h number of re(281,288, 417,600,688,967,1295). view articles o n carbohydrate chro-4s a n example of the range of submatography have recently appeared stances separated, there may b(1 men(249, 623, 857, 1017, 1170, 1301). tioncd: cy- and 0-naphthol (I$%$), BisFor the fractionation of oligo- and phenol -1 (197), o-hydroxybiphenyl polysaccharides, adsorption chromatog(1183). halogenated phenols @ l o ) ,antiraphy on columns (51, 132, 769, 760, oxidants (989, 100S), urinary phenols ?64,1132, 1208) continues to be the (997), phytoestrogcns (224), vanillin method of choice, with gradient elution (157, 1195),hashish (618), and miscel(132, 759, 760) as a notable technical laneous flavonoids (70, 83, S11,351, 436, improvement, but gel filtration (324, 652, 7'50, 1292). 832) offers some interesting possibilities Roux aiid hIaihs (9S6) have pubof separation according to the degree lished a list of selective spray reagents of polymerization. There have only for flavonoids, S e u (811) has devised been two reports so far on the use of thina specific test for flavanones and layer chromatography for the resoluflavanonoles, and Stcelink (1151) has tion of monosaccharide mixtures (868, described color reactions with Ehrlich's 1119), aiid one on the use of dichroreagent. Other reagents in the curmate-treated glass-fiber paper (528). rent literature include Fast Red Salt Paper chromatography (308, ~ $ 2 ,853, G G (872), titanium salts (729), a 1510) has been applied to sugars in urine neutral silver nitrate reagent (158), (322, 898, 1181) and plant material and phenitrazole-perchloric acid (1066). (221, 869), to hexosamines (450), Paper impregnated u-ith -41, Be, or hexuronic acids (734), methyl sugars Zr salts permits the detection of flavo(627), sialic acid (129, 192, 1256), noids by fluorescence (506). Fluoriacetonides (1137), acetals (839), disacmetric methods are often used in quanticharides (899, lW84), mucopolysactative work (283, 461, 679). Other charides (547, 1113, and hydrolyzed quantitative estimations may be based cellulose esters and ethers (718). The on iodometry (1077) or on colorimetry partition system may be scaled up by use after coupling n i t h diazonium salts of a cellulose column (1184). Salts (313, 776). do not serm to interfere in paper chroTerpenoids. Porter and Anderson matography (898, 905). Kew color (930) have nritten a chapter covering reagents (948)include : p-aminobenzoic this field of application and C a h a r a n o acid, followed by oxalic acid (991), (173) has reviewed the chromatographic sodium hypochlorite, followed by tolanalysis of essential oils. Aloderately idine-potassium iodide (for amino acidic alumina can be used for terpenes, sugars) (411), diphenylamine-aniline b u t isomerization may take place on (50), sodium methoxide-picric acid this adsorbent (1130). Silica gel is (169),thiobarbituric acid (for deoxy suitable for column chromatography sugars) (1018, 1256), and a very specific (360) and rubber makes a very good VOL 34, NO. 5. APRIL 1962

17 R

packing material (146). For small quantities, thin-layer chromatography is ideal (144,895, 1197, f 2 7 5 ) ,b u t paper impregnated with alumina (861, 875), kieselguhr (552), or Quilon (875) can also be used. Conventional paper chromatography (187, 637, 548, 584, 818, 1014) and centrifugally accelerated paper chromatography (26) have been applied, b u t reversed-phase chromatography (467,918) seems more appropriate for the nonpolar substances in this group. Steroids. Summaries of this field of application have recently been presented by Bush (160), Heftmann (468), and S e h e r (806). N o r e limited reviews are available on the chromatography of sterols (1176), estrogens (149), adrenocortical steroids (159, 781), and ketosteroids (17 4 ) . The adsorption isotherms of corticosteroids have been determined by Crzua (1211 ) . Adsorption chromatography on alumina is still widely used for the separation of estrogens (649, 831, 990), androgens (309, 798), and progesterone metabolites (331, 676, 725), b u t silica also enjoys well deserved popularity as adsorbent (535, 826, 856, 1308, 1309) or carrier of the stationary phase of partition systems (26, 392, 935). Other packing materials in the recent literature are: Florisil (88, 350, 1159), Celite (389), and cellulose (96,293, 392). .in interesting method of purifying estrogencontaining extracts depends on successive filtration through NazC03, AIgCOQ, and BaC03 (182). Teflon columns with a n elution gradient of irater in methanol have been used for the separation of sterols (32). For weakly polar steroids, thin-layer chromatography (56, 58, 356, 668, 1120, 1215, f2l4) has been found to be most useful; also spread-layer chromatography (195, 473, 1126), a n analogous technique in which the adsorbent is not mixed with a binding agent. Other variants of this principle t h a t have been successfully applied are glasspaper chromatography (263, 443, 1129, 1161) and adsorption chromatography on impregnated (606, 875) or nonimpregnated (198, 801, 865, 968)paper. The majority of the recent publications on steroid chromatography deal with partition on filter paper, e.g., the analysis of sterols and their esters (634, 749, 817, 874), estrogens (141, 232, 512, 1073), androgens and their derivatives (171, 232, 286, 638, 879, l l 2 4 ) , corticosteroids ( 1 , 147, 188, 225, 232, 693, 866, 879, 1098, 1099, f 262) and other pregnane derivatives (134, 286, 638, 1073), bile acids (556, 659), cardiac glycosides (1201), and saponins (862). Paper chromatography has also been used for the study of sterol adduct formation (743) and for structure correlations (159, 160, 544).

18 R

ANALYTICAL CHEMISTRY

New solvent systems for conventional (162, 648, 1123,1166,1127,1167,1193) and reversed-phase (181, 261, 269, 458, 756, 1194) partition chromatography have been devised and acetylated paper has been recommended for various applications in steroid work (464). Elevated temperature is not required for aqueous solvent systems, if the paper has been impregnated with 90% methanol (1204). Repeated solvent development sharpens the zones and increases resolution (942). Improved detection methods have been proposed for sterols (44, 558, 1167), estrogens and ketosteroids (43, 44,558), pregnane derivatives (43-5, 100, 472, 558), and digitalis glycosides (471). For the quantitative estimation of steroids (4), densitometry (161, 476), elution (507, 1095, l280), and tracer techniques (264, 601, 732, 979, 1160, 1263) are employed. Alkaloids. Two recent review chapters summarize t h e progress in this field (625, 980). In addition to alumina (917 ) and silica (28), stereoselective adsorbents (77) have been used for column chromatography. Kori et al. (617 ) have separated opium alkaloids on two partition columns a t different pH, connected top to bottom. Thinlayer chromatography has been applied to minute amounts of alkaloids (721, 790, 1032, 1247). Linear (90, 246-8, 374, 379, 503, 548, 735, 800, 947, 1187, 1234), radial (231, 762),and centrifugally accelerated (239) paper chromatograms are developed, usually with buffered solvent systems. Succinyl cellulose paper has been tried (761). Comparison of R p values in formamide- and formamideammonium formate-impregnated paper has been used in structure elucidation (695). For citrate-buffered paper the application of a barium salt and ammonia has been recommended to facilitate the elution of alkaloids with chloroform (218). Detection methods in recent publications include sulfanilic acid (for quinine) (422), isatin (for certain piperidine and pyrrolidine alkaloids) (689), acetic anhydride (for 'Y-oxides of pyrrolizidine alkaloids) (241), mercury vapors, followed by a 2-naphthylamine spray (for nicotine) (911), and radioactive phosphomolybdic acid (for Strychnos alkaloids) (1016). The sensitivity of the Dragendorff reagent is increased tenfold by treatment of the spot n i t h O.05N H2S04 (1212). Alkaloids may also be detected on the moist paper by potentiometry (397,1248). Vitamins. R e v i e w on t h e chromatographic analysis of fat-soluble vitamins have been prepared by Lederer (653), by Porter and Anderson (950), and by Suzuki (1158). Vitamin A concentrates have been chromato-

graphed on columns of alkali-deactivated clay (481). Thin-layer chromatography has been used for tocopherol mixtures (f057, 1058), and impregnated filter paper for all fat-soluble vitamins (270, 402, 876). The water-soluble vitamins have been reviewed by hIunier (792) and by Schoen (1038). Column chromatography m s employed in the isolation of vitamin B1? (722) and of niacin (848). There have been reports on the use of thin-layer chromatography for the separation of vitamins of the B group and ascorbic acid (367) and for pteridines (816). Paper chromatography has been applied to vitamins of the B complex (110), particularly thiamine and its derivatives (615, 1060), nicotinamide (537), vitamin BI2 (469), paminobenzoic acid (48,644), and to vitamin C (196,306,870). Nucleic Acid Components. A comprehensive coverage of the field niay be found in Lederer's book (127). In spite of the obvious advantages of ion exchange chromatography, some progress may be recorded in the fractionation of nucleic acids on columns of kieselguhr (716),esterified bovine serum albumin (900),and silicic acid (298) and of nucleic acid components on columns of modified calcium phosphate (707) and activated charcoal (1121). Very extensive work on the application of paper chromatography was published by Venner (1220). 1Ionophasic solvent systems appear to be very suitable for the fractionation of purines, pyrimidines, nucleosides, and nucleotides (192, 1140). In fact, thinlayer chromatograms (949) on plates prepared from cellulose powder in acetone are claimed to be quicker and more sensitive than conventional paper chromatograms (20, 145, 631, 1288). S e w solvent systems for partition chromatography on paper have been published (238, 551, 637, 696, 698, 1285) and also home novel detection procedures, e.g., the murexide test (200, 1166) and a method of revealing nucleic acids with basic dyes (1079). -Adenine gives white spots on a black background if kept on silver arsenateimpregnated paper in the dark (606), and thymine and uracil undergo photolysis a t different rates when exposed to ultraviolet radiation (610). Porphyrins. This topic has been reviewed by Biserte (f02),Falk (300), and Strain (1146). .Idsorption columns have been used for bile pigments (117 , 1205) and petroporphyrins (497). Plant (26, 1015) as well as animal (609, 912, 972, 1020, f022) porphyrins have been separated b y paper chromatography. Antibiotics. Three comprehensive revien s o n antibiotic Chromatography have been published in t h e last two years (f 001, 1Of 1, 1038). Purification

has been effected on adsorption columns of talc (779), activated charcoal (140, ff68), and Celite (284, 285). For analytical M ork, thin-layer chromatography on silica gel (1062), salting-out chromatography (233, 1210), and partition chromatography on paper (661, 825, 901, 941, 1108, 1306) have been applied. The dependence of the RF of amphoteric antibiotics on pH may be euploited for their effrctive resolution (92). Cytotoxic agents m a y be detected by bioautography, using tissue cell cultures on agar plates (4O6), and antiviral agents are similarly revealed n i t h the aid of virus-infected chick embryo cells (475). I n cases where bioautogiaphy is not applicable, antibiotics may be detected in ultraviolet light (109, ego), cspecially after exposure of the paper to animonia (126, 576). Penicillins are revealed by spraying with iodic acid (315) or starchiodine (1101), those with a closed lactnm ring by spraying again with pcnicillinase ; penicillinase is revealed by spraying n ith starch-iodine and penicillin. Pharmaceuticals. T h e application of chromatogrnphy to pharmaceutical analysis has been rcvicned (240, 1150) and some publications (leal with a varioty of drugs (366, 1044, 1067). Most of the rrcciit papers were concerned n ith the a n a l p i s of barbiturates (317,344,5+$6, 656, 655,720, 1000, 1236) and sulfonamides (33, 136, 228, 1086, 1110, 1172). I n addition, u-ork has been rcportcd on analgesirs (115, 273, 915, 974), ancathetics (151) 609, 1165), diuretics (172), antihistamines (152), sympathoniinic.tic3 (610, $?20),salicylate? (316, 423, 742), anticoagulants (65.9 I , anthraquinone drugs (40),stilbestrol diphosphate (697), aloin (121), and glycyrrhizic acid (143). Pesticides. Chromatographic methods have been described for organophosphoru,. (?OR, 139, 757> 772, 1019) and arqeno organic (770) compounds, for pyrethrum constituents (1096, 111 7 , 1136), carhaiiiatcs (700, 765, 1186), dalapon (354),amizol (771), lindane (349), phmothiazine (&%if and TI arfarin (1147). ;\loreover, some general 1xocedurc.s for the analysis of 1)wticides by silicic acid (68) and paper (701) chromatography have k)ecn outlined. Dyes. Stnmm and Zollinger (11,%?) have contributed a chapter on this topic. Thc bvhaxior of azo dyes on alumina columns has b w n studied (1254). Ccllulov column5 (307) and paper chromatography have been applied not only to azo (368, 626, 6b3, 1100)and thiazine dyes (1178),but also to broinosulfalein metabolites (335) and dye intermediates (691, 592). Identification of dyes in food (62, ,%I), gasoline (460),inks, and lipsticks (1180) is important in lam enforcement.

Polymers.

Column

chroniatog-

raphy of polymers has been discussed by Schneider (1036). Examples of such techniques are the fractionation of pyrocatechol polycondensates on polyamides (620) and of alkyl polyoxyethylene condensates, in the form of azoates, on alumina (943). Paper chromatography is applicable t o various synthetic polymers (388, 646, 887), as ne11 as to their azo dye derivatives (961) and dinitrobenzoates (120). Miscellaneous. T h e chromatogr a p h y of nitro compounds has been suniniarized by Dietrich (265) and there are some recent reports on the separation of nitroalkanes (577, 992) and aroniatic nitro compounds (886, 1,394). Halogenated compounds were reriewed by Lederer (651) (cf. 1216) and sulfur compounds by Froniageot (347) (cf. 606). Chromatographic data h a w been published for surface active agents (511), gasoline additives (1069), plasticizers (873), peroxides ( I S Z ) , organic mercury compounds (&%), and nitrogen mustards (1007). LITERATURE CITED

(1) Abelson, D., Jfeni. Soc. Endocrinol. 8, 63 (1960). (2) Abelson, D., AVature 188, 850 (1960). (3) Abelson, D. AI., Bondy, P. IC., Piskorski, J., J . Chromatog. 5, 332 (1961). ( 4 ) Abelson, D., Brooks, R. V., eds., “Quantitative Paper Chromatography of Steroids,” .1fe??i. SOC.Endocrinol. 8 , University Press, Cambridge, 1960. (5) Abelson, D. A I . , Fox, J. G. C., J . Clzn. Pathol. 12, 375 (1959). (6) Xcland, J. D., Johnson, S., J . Chromatog. 5, 363 (1961). (7) .\der, I)., hlon, A., zlnalyst 86, 125 (1961). (8) .%garid, V. D., Sigam, I. C., J . Proc. Oil Technologist dssoc., Indza, Kanpzkr 15, Pt. 2, 61 (1960). (9) -\grinier, H., B u t zizj’orni. scz. et tech. (Parzs) S o . 4, 2 (1957). (10) Agrinier, H., Chzirz. anal. 42, 600 i 1960). -(11) Xgrjnier, \ -

H., Compt. rend. 249, 2365 (1959). (12) Akazawa, T.,JTada, K.,d g r . Bzol. C’hem. ( T o k y o ) 25, 30 (1961). (13) Akerfeldt, S., Acta Chein. Scand 13, 627 11959). (14) Alberti, G., Grassini, G., J . Chromatoq. 4, 425 (1960). (15) Ibicl.) p. $23. (16) Alderii eireldt, F., Ibzd., 5, 98 (1961). (17) .%leksandrova, L. S., Chmutov, K. V., Izvest. ARad. AVauk S.S.S.R., Otdel. Khzni. -1a u k 1960,801. (18) Alekeeenko, L. P., and Orekhovich, V. S . , Dohlady dkacl. .\auk S.S.S.R., 13, 690 (1960). (19) Alexa, J., Cheiri. lzsty 53, 761 (1959). (20) Miniova, E. K., Bolgova, G. D., detvatsatur’y:in, -4. T., Rbokhinzzya 26, 221 119611. (21) Aliniova, E. I Bolyova, G. D., PustovoItova, 0.K., Ibzd., 25, 773 (1960). (22) hlmhssv, G., Ordogh, AI., Hadobhs, B., M a g y a r Tudo?iktLnyosd k a d . Kozpontz Fzz. Kutatd IntPret6nek Korleinenyez 7, 67 (1959). (23) Anibe, K. S., Tappel, .A. L., J . Chromatog. 5 , 546 (1961). (24) AYAL.CHEM.33, S o . 11, 48.A (1961). (25) Anderson, F. O., Crisp, L. R.,

Riggle, G. C., Vurek, G. G., Heftmann, E., Johnson, L). F., Francois, D., Perrine, T. D., A N ~ LCHEM. . 33, 1606 (1961). (26) Anderson, J. RI., J . Chromalog. 4, 93 (1960). (27) -Anderson, X. G., .\SAL. CHEM.33, 970 (1961). (28)Andreeva, L. G., -1plechnoe Del0 9, S o . 1, 51 (1960). (29) Anselmi, S., Oleuria 15, 61 (1961). (30) hntoszewski, R., Iinypl, J. S.,Z . anal. Ckevi. 169, 269 (1959); Jfzkrochini. .Icta 1960,325. (31) .ircus, -4.C., J . (‘hroniutog. 3, 411 11960). ( 3 i ) Arcus, A. C., DunchleJ , G. G., Ibzd., 5 , 272 (1961). (33) Ari, X., Turk Ijien Tecrubi Biol. Dergisz 19, 14 (195‘3). (34) Xrimura. .I..L)inrr~nnn.J. F.. S u t u r e 184, Suppl. KO. 24,787-1 (195‘3). (35) L4satoor, -1. J . Chroniatog. 4, 1-14 (19)AOi \ - - - - /

(36) hshizawa. T., Buiisekz Kagaku 10, 354 (1961). (37) Asniaev, P. G., IIokhnachev, I. G., Izvest. Vusshtkh Ccheb. Zavedenzi. Pishchevaya i’ekhnol. 1960, KO.5, 160. (38) Asselineau, J., in ‘Chromatographie en chiniie oryaniquP et biologique” (E. Lederer, ed.), Vol. I, Part 11, Chap. 5, Masson et Cie., Paris, 1959. (39) Ibid., T-ol. 11, Part 111, Chap. 5 , 1960. (40) Auterhoff. Auterhoff, H.. H., JIaiss. JIaiss, N.. N., Deict. Deut. ’ dpotheker-Ztg. Lipotheker-Zig. 98; 98, 650 (li58). (1958). (41) Avgul, V. T., Batrukov, V. S., Chniutov, IC. V,, Zhiir. Fiz. Khinl. 34, 460 (1960). (42) .lnapara, J., Davis, \-. E., Graham, O., J . Chromatog. 3, 11 (1960). ($3) .-\selrod, L. R., Pulliam, J. E., A b a ~ . CHE3I. 32, 1200 (1960). (44) .iselrod, L. R., Pulliam, J. E., -4rch. Biochem. Biophys. 89, 105 (1960). Badinand, -I.,Revol, A A,, (45) Badinand. , . Riol. n&d. ( P a r zi s ) 47, 161 (1958). (46) B)ehler, B., Schwei?. ,lpotheker-Ztg. Apotheker-Ztg. 99, a43 (1961). (47) Baer, E., Buchnea, I]., Gr:r6f, T.. (47) Can. J . Htocheni. Hiocheni. a n d Phrlszol. Phjlsiol. 38, 853 (1960). (48) Bagdasarian, G . , Paivelec, J., Grublica 27, 843 (1959). (-19) Bailey, G. F., - 1 x . i ~ . C m x 32, 1726 (1960). (50) Bailey, R. IT.> Bourne, E. J., J . Chronratog. 4, 206 (1‘360). (51) Ballio, =2., Russi, S., Ibid., 4, 117 (1960). (52) Bandelin, F. J., Tuschhoff, J. V., J . .i)n. Phurnz. .issoc. 49, 302 (1960). (53) Baptists! A . IT.,Ramalho, -4. J. G., de Mato Fernandes, -4. X., Intern. J . - 4 p p l . Radiation and Isotopes 5, 289 (1959). (54) Barashliov, G. IC.,Lab. Del0 6, No. 6,44 (1960). (55) Barbier, bl., J . Chromatog. 2, 649 (1959). (56) Barbier, M., Jager, H., Tobias, H., IJ-yss, E., Helv. Chinz. ; I d a 42, 2440 (1959). (57) Barbier, >I., Yinogradova, L. P., Zav’pdov, S. I., Izcest. A k a d . Sauk S.S.S.IZ., Otdel. Khiui. .Vauk 1961, >

-

~

162.

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20R

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I

( l Y 3 Y ).

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c.,

VOL. 34, NO. 5, APRIL 1962

27 R

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28R

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(1120) Ibid., p. 458. (1121) Stambaugh, R. L., Wilson, D. W,, Ibid., 3, 221 (1960). (1122) Stamm, O., Zollinger, H., in “Chromatographie en chimie organique et biologique” (E. Letlerer, ed.), Vol. I, Part 11, CLap. 10, hlasson et Cie., Paris, 14.54

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