Anal. Chem. 1980, 52, 4 2 R - 5 0 R
the nucleic acid is first modified with chloracetaldehyde to give etheno derivatives with adenine and cytosine, then each adenine residue will also bind an Os atom (31). An elegant procedure for roducing double stranded DNA with particular nucleotides lateled was introduced by Strothkamp and Lippard (32) who incorporated phosphorothioate groups into DNA in a n enzymatic synthesis and showed the sulfur-containing nucleotides specifically bound t o platinum atoms. These reactions allow specific labeling protocols for various groups of bases in nucleic acids and promise to be useful in establishing sites of binding of proteins. For labeling proteins the compound (Gly-L-Met) PtCl has been shown to bind only t o methionine residues in collagen and electron micrographs show reaction a t the sites expected from the known methionine positions (33). A similar specificity for methionine was found by Dumont and Wiggins who studied the reactions of this reagent in the membranes of the purple bacterium Halobacterium halobium (34). Finally it has recently been shown that certain Os(V1)ligand complexes react with sugar residues. Again electron micrographs or aggregates of the glycoprotein rat tail tendon collagen showed density only where amino acid sequence analysis established the sites of glycosylation (33). Use of the above reagents is a t an early stage. Yet when used in conjunction with microscopes able to image the larger atoms, they show considerable promise in the localization of various chemical groups within macromolecules or cells. LITERATURE CITED
(1) Unwin, P. N. T.; Henderson, R. J. Mol. Bid. 1975, 94, 425-440. (2) Chiu, W.; Glaeser, R. M. J. Mol. Biol. 1978, 122, 103-107. (3) “Regular 2-D Array of Biomacromolecules: Structure Determination and Assembly”; workshop held in Burg Gemen, Germany, June 17-21, 1979; Springer-Verlag: West Berlin and Heidelberg, 1979, to be published. (4) Hayward, S. B.; Glaeser, R. M.; Ultramicroscopy 1979, 4 , 201-210., (5) Taylor, K. A,; Glaeser, R. M.; J. Uffrastruct. Res. 1976, 55, 448. (6) Hayward, S. B.; Glaeser, R . M. Ufframicroscopy, in press.
(7) Fox, F.; Knapek, E.; Weyl, R. Electron Microsc., Proc. Int. Congr., 9th, 1978. 1978. 2. 342-343. (8) Dietrich, I. Electron Microsc., Proc. Int. Congr., 9th, 1978, 1978, 3 ,
173- 184. (9) Dubochet, J.; Knapek, E. Chem. Scr. 1978-1979, 14, 267-269. (10) Ramarnurti, K.: Crewe, A. V.; Isaacson. M. S. Ultramicroscopy1975, I . 156-1 58. (11) Dubochet, J. J . Uffrastruct. Res. 1975, 52, 276-268. (12) Voreades, D.; Wall, J. S. 37th Annual EMSA Meeting, San Antonio, 1979, pp 358-359. (13) Van Harreveld, A.; Crowell, J. Anat. Rec. 1900, 19. (14) Heuser, J. E.; Reese, T. S.; Dennis, M. J.; Jan, Y.; Jan, L.; Evans, L. J. Cell. B i d . 1979, 81, 275-300. (15) Costa, J. L.; Joy, D. C.; Mahr, D. M.; Kirk, K. L.; Hui, S. W. Science 1978, 200, 537-539. (16) Simon, G. T.; Ottemsmeyer, F. P. Thirty-seventh Annual EMSA Meeting, San Antonio. 1979. DD 510-511. (17) Zeitler, E.; Bahr,’G.-F. J. Appl. Phys. 1962, 33, 847. (18) Engel, A. Ufframicroscopy 1978, 3, 273-281. (19) Wall, J. S. Scanning Electron Microsc. 1979, 2 , 291-302. (20) Woodcock, C. L. F.; Fredo, L.-L. Y.; Wall, J. S. J. Cell. Biol. 1979, 83, 156a. (21) Crewe. A. V.; Wall, J.; Langmore, J. Science 1970, 168, 1338-1340. (22) Henkelrnan. R. M.; Ottemsmever. P. F. Proc. Nat. Acad. Sci. USA 1971, 68, 3000-3004. (23) Kihlbong, L.. Ed.; Chem. Scr. 1978-1979, 14, 1-295. (24) Isaacson, M.; Kopf, D.; Uthnt, M.; Parker, N. W.; Crewe, A. V. Proc. Ut/. Acad. Sci. USA 1977. 7 4 . 1802-1806, (25) Langmore, J. P.; Crewe,’ A. V. 32nd Annual EMSA Meeting, St. Louis, 1974, pp 376-377. (26) Lipka J. J.; Lippard, S.J.; Wall, J. S. Science 1977, 206, 1419-1421. (27) Cole, M. D.; Wiggins, J. W.; Beer, M. J. Mol. Biol. 1977 117, 387-400. (28) Germinario, L. T.; Reed, R.; Cole, M. D.; Rose, S. D.: Wiggins, J. W.; Beer, M. Scanning Nectron Microsc. 1978, 1 , 69-76. (29) Stewart, M.; Diakiw, V. Nature(London) 1978, 274, 184-186. (30) Chang, C.-H.; Beer, M.; Marzilli, L. Biochemistry 1977 16, 33-38. (31) Marzilli, L. G.; Hanson, B. E.; Kapili. L.; Rose, S. D.; Beer, M. Bioinorg. Chem. 1978, 8, 531-524. (32) Strothkamp, K. G.; Lippard, S. J. Proc. Natl. Acad. Sci. USA 1976, 73, 2536-2540. (33) Beer, M.; Wiggins, J. W.; Alexander, R.; Schettino, R.; Stoeckert, C.; Piez, K. A. 37th Annual EMSA Meeting, San Antonio, 1979, pp 28-29. (34) Dumont, M. E.; Wiggins J. W. J . Supramol. Struct. Suppl. 3 1979, 114.
Organic Elemental Analysis T. S. Ma” Department of Chemistry, City University of New York, Brooklyn, New York 11210
Mllton Gutterson Flavor Application Laboratory, Dragoco Inc., King Road, Totowa, New Jersey 075 12
GENERAL This review follows the previous one (1) and covers the literature from December 1977 to September 1979. The reader is referred to a recently pubIished comprehensive treatise on organic elemental analysis (2) in which the senior author described a number of unpublished methods t h a t are in operation in various laboratories. These methods will not be cited in the present review. After the normalization of U. S.-China relations in 1979, the senior author went to China for a three-month lecture tour and visited more than 30 research institutions in 12 cities. It was noted that there were many innovations in organic microanalysis and several automated devices were constructed in China (3),but most of the research work has not been published. A major development in the large organic analytical laboratories during recent years ( 2 ) is concerned with the computerization and data processing of elemental analyses that are amenable to total automation. Some programs have been evaluated. Thus Bramstedt and Harrington ( 4 ) published 42 R
0003-2700/80/0352-42R$Ol .OO/O
results indicating that a C-H-N system can be automated and computerized for increased flexibility while maintaining a high degree of accuracy and precision. van den Bosch et al. ( 5 ) developed a microcomputer for data processing of C-H-N and 0, C-H-N and S, or 0 and S. Brodkorb et al. (6) described analyzers for C, H, S, and halogens; readings are classified and data are printed out by computer, inconsistent results being signaled by an alarm device. Merz (7) discussed the rapid determination of C, H, N, 0, S, and halogens and pointed out some limitations of these methods. Eastin (8) described an automated spectrophotometric finish of semimicro-Kjeldahl analysis with results similar to those obtained by distillation and titration. Nowadays most organic materials submitted for analysis are mixtures (9). For the determination of the elements in these materials, improvements of the techniques for the destruction of organic matter were studiously investigated, such as the Kjeldahl digestion procedures (10-14). Erni and MWer (15) worked out a mathematical model for the optimization
0 1980 American
Chemical Society
ORGANIC ELEMENTAL ANALYSIS
T. S.Ma is professor of chemistry at the City University of New York. He received his Ph.D. in synthetic organic chemistry from the University of Chicago in 1938 and started his career as a teacher of microchemistry in Chicago. Subsequently, he established microchemistry laboratories and taught at Peking University, China: University of Otago, New Zeaiand; and New York University. Prof. Ma has been particularly active in promoting the application of microchemistry to research and education and has lectured widely on this subiect. He served twice as Fullbriaht-Haves ieckrer and once as American specialist with the Bureau of Educational and Cultural Affairs of the State Department He has been visiting professor at Tsinghua University, Lingnan University, and National Taiwan Universlty China, Chtangmai University, Thailand, and University of Singapore, Republic of Singapore Prof. Ma has published six books and over 140 papers. He is an editor of Mkrochmm Acta the international journal on microchemistry and trace analysis. His current research interests are concerned with organic synthesis and analysis on the mg to Fg scale, microchemical investigation of medicinal plants, and the use of small-scale experiments to teach chemistry. Prof. Ma received the Benedetti-Pichler award in microchemistry in 1976.
Mllton Gutterson received his B.S. degree from the City College of the City University of New York in 1949. After graduation he worked for Popsicle Industries (formerly Joe Lowe Co.) Division of Consolidated Foods Corp., Englewood, N.J., where he was chief chemist and then plant manager. He has since worked for Ehlers Division of Brooke Bond Foods Inc. He is now connected with Dragoco, Inc., Totowa, N.J., where he is director, Flavor Application Laboratory. For several years he was a part-time lecturer in the graduate division of Brooklyn College, City university of New York, where he supervised the laboratory for auantitative elemental and functional group microanalysis. He earned his master's degree from Brooklyn College in 1956 by attending classes and doing research after working hours. His special interest is in the field of organic microanalysis. He was adjunct professor of chemistry at the New York Institute of Technology, Manhattan Campus, evening division. Mr. Gutterson recently published several monographs on food processing with the Noyes Data Corp., Park Ridge, N.J. These were titled "Baked Goods Production Processes, 1969", "Confectionary Products Manufacturing Processes, 1969", "Fruit Juice Technology, 1970". "Fruit Processing, 1971", and "Vegetable Processing, 1971". He is a member of the ACS, the American Association of Cereal Chemists, and the Institute of Food Technologists.
of continuous-flow analysis of Kjeldahl nitrogen and phosphorus. Optimization of the procedure of biological materials for selenium determination (16) involved using a digestion mixture containing Na2Mo04,HZSO4,and HC104. Wet-destruction of dry organic material in a closed quartz tube (17), and digestion in sealed, disposable polystyrene vessels (18) were advocated for certain samples. Low temperature plasma ashing was used in the analysis for phosphorus (19) and metallic elements (20). Photochemical reactions were utilized to decompose polyfluro (21) and organomercury (22) compounds. In the determination of trace constituents, contamination of the sample and loss of the element during preparation sometimes present serious problems (23). Gardner (24) described the determination of mercury in coal and organic matter with minimal risk of contamination. Scoble and Litman (2.5) reported a washing process for removal of surface contaminants from hair and nail samples for trace element analysis. Smith (26) discussed the sources of copper and cadmium contamination in small biological samples. Losses of elements during sample decomposition in an acid-digestion bomb ( 2 7 ) ,dry-ashing (28),or lyophilization (29, 30) were reported. In blood analysis for lead, Unger and Green (31) found that up to 52% of the lead could be lost to the glass or polyethylene container in 5 days; by adding H N 0 3 or HzOZ to the sample, the loss was reduced to 6%.
CARBON, HYDROGEN, NITROGEN While C-H-N analyzers are commercially available in several countries, some laboratories preferred to construct their
Table I. Trace Analysis of Nonmetallic Elements element antimony arsenic
bismuth boron bromine carbon fluorine
iodine
sulfur
material analyzed
mode of finish
ref.
biological biological biological biological biological biologica 1 biological biological bi o logica 1 air water water biological biological biological plants biological biological biological biological milk milk milk plants fats organic organic Detroleum plants
atomic absorption neutron activation atomic absorption atomic fluorescence gas chromatography polarography atomic absorption colorimetry neutron activation gravimetry gas chromatography polarography molecular absorption ion-probe gas chromatography F-electrode, Th(NO,), colorimetry neutron activation photon activation X-ray fluorescence colorimetry X-ray fluorescence gas chromatography colorimetry colorimetry colorimetry isotope dilution coulome trv turbidimetry
180 181 182-184 185
186 187 188, 189
190 191
192 193 194 195 196 197 198,199 200 201, 202 203 204 20 5 206 207 208 209 210
211 212 21 3
own devices. Fraisse e t al. (32) developed an apparatus in which the sample is combusted in helium-oxygen in a vertical tube, and the COz, HzO, and N2 are measured by thermal conductivity. For the determination of carbon and hydrogen only, Houde and Champy (33)employed coulometric titration in nonaqueous medium monitored by a computer; other workers (34-36) used a gravimetric finish. Sakla and Shalaby (37) studied the determination of carbon alone by closed flask combustion followed by atomic absorption, gravimetric, and titrimetric finishes respectively, and found that all gave the same results. Troeltzsch (38) oxidized samples which may explode or form carbides during dry combustion with a solution containing H2S04,H3P04,P2OS, CrO,, and KIO,. Puxbaum and Leyden (39) determined carbon in oil shale by heating rapidly in oxygen and measured the C 0 2 conductometrically after absorption in NaOH. Yoshimori and Katoh (40) determined microgram amounts of carbon by absorbing the COz in dimethylformamide containing ethanolamine and titrating with (C4H9),NOH in benzene-methanol. Determination of carbon-14 in plant materials involved drv combustion (41-43) or oxidation in H2S04-KzCr207(44). Determination of hvdrogen in hvdrocarbons. etc. was effected by neutron-reflection (45),neutron-transmission (46), and 0-plasma (47)techniques. Tritium in organic materials was determined by isotope exchange (48). Hydrogen isotope ratios were determined in a microwave-induced plasma (49). Kjeldahl digestion followed by distilling the NH3 into boric acid solution and titrimetry gave good results for nitrogen in plant materials (50). Spectrophotometric finishes were also electrode was used employed (51-54). When an ",-selective without distillation, Rial-Varela (55) found positive errors of 10 to 50% unless certain corrective measures were taken. For the determination of microgram amounts of nitrogen, Madrowa (56) described a technique which involves distillation and spotting on anion-exchange paper. Hegedus and Forgo (57) observed positive errors when an automated nitrogen analyzer was used to analyze N-methyl compounds due to the formation of CH,; satisfactory results were obtained when the combustion temperature was raised to 1150 "C. The presence of fluorine also produced positive bias due to the formation of polyfluorocarbons; this difficulty could be circumvented by mixing the sample with NaC10, (58). Miyahara and Kameyama (59) used WO, to prevent the interference of iodine in the sealed-tube combustion. Several ANALYTICAL CHEMISTRY, VOL. 52, NO. 5, APRIL 1980
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ORGANIC ELEMENTAL ANALYSIS
Table 11. Trace Analysis of Metallic Elements element aluminum barium beryllium cadmium
caesium calcium
chromium
.
cobalt
europium gold iron
lead
lithium magnesium maganese mercury
material analyzed
mode of finish
ref.
biological biological biological biological biological biological biological biological biological fish fish foods plants plastics biological biological biological biological fruits milk biological biological cereals biological biological pharmaceutical plants biological biological biological biological plants biological biological biological biological biological foods foods plastics biological biological biological biological foods foods foods petroleum plants plastics biological wines biological biological petroleum biological bi 010 gi cal biological fish foods foods
fluorimetry atomic absorption neutron activation neutron activation emission spectrometry atomic absorption atomic absorption atomic fluorescence isotope dilution atomic absorption mass spectrometry atomic absorption photoacoustic absorption atomic absorption atomic absorption atomic absorption colorimetry He-glow photometry colorimetry titrimetry atomic absorption isotope dilution atomic absorption atomic absorption neutron activation colorimetry colorimetry atomic absorption neutron activation nuclear resonance mass spectrometry atomic absorption neutron activation atomic absorption atomic absorption colorimetry electrolysis colorimetry atomic absorption colorimetry atomic absorption polarography emission spectrometry X-ray fluorescence colorimetry atomic absorption polarography X-ray fluorescence atomic absorption atomic absorption atomic absorption mass spectrometry colorimetry atomic absorption atomic absorption atomic absorption neutron activation emission spectrometry atomic absorption atomic absorption colorimetry neutron activation atomic absorption atomic absorption colorimetry colorimetry neutron activation colorimetry atomic absorption atomic absorption atomic absorption radioactivity atomic absorption neutron activation atomic absorption ion-selective electrode atomic absorption
214 215-217 218-220 221 222 223, 224 225-227 228 229 230 231 232 233 234 235 236 237 238 239 240 24 1 242 243 244 245 246 247 248 249 250
foods
molybdenium
nickel platinum plutonium rubidium silver sodium strontium 44R
fuel plants plastics biological biological plants plants biological biological biological biological plants biological biological biological
ANALYTICAL CHEMISTRY, VOL. 52, NO. 5, APRIL 1980
251
252,253 254 255, 256 257 258-261 262 263 264 265 266-27 1 27 2 27 3 27 4 27 5, 27 6 27 7 27 8 27 9 280 281 282, 283 284 285 286-288 289 290-293 294, 295 296 297 -30 1 302, 303 304 305
306 307, 308 309 310 311 31 2 313 314, 315 316-318 319-32 3 324 325 326, 327 328 329
ORGANIC ELEMENTAL ANALYSIS
Table I1 ( C o n t i n u e d ) element tantalum t ha Ili u m thorium tin uranium vanadium
zinc
zirconium
material analyzed milk biological biological biological biological foods biological biological biological foods petroleum plants biological biological biological petroleum pharmaceutical pharmaceutical
workers (60-63) reported on the determination of nitrogen-15 in organic materials.
OXYGEN, SULFUR, HALOGENS Kirsten (64) described a procedure for the determination of oxygen by volatilizing the sample and pyrolyzing it at 1050 "C in a silica tube which contains nickelized carbon and through which He gas asses; the CO formed was separated by molecular sieves. Ehumachenko and Varderesyan (65) determined oxygen in organophosphorus compounds using carbon a t 1150 "C in a tube which is connected to a gas chromatograph. Imaeda et al. (66)analyzed fluoro compounds in a vitreous carbon pyrolysis tube packed with silica wool to remove HF. Bichaev e t al. (67) determined oxygen in biological material by burning it in "0 and passing the combustion gases through carbon a t 1100 "C to convert the 0 to CO, which was analyzed by emission spectroscopy for " 0 to give the oxygen content of the original sample. Thompson and Gra (68)described a method to determine the ratios of " 0 to 0 in C-H-0 compounds. Maciak et al. (69)developed a computerized technique to determine sulfur which involves combustion in empty tube and titration of the H2SO4 with Ba(C104)2. Hozumi et al. (70) recommended a glass electrode to detect the end point when 5 mM BaC12 was used as titrant, while Burgasser et al. (71) monitored Ba(C104)2 titration by menas of a colorimeter equipped with a 520- or 450-nm filter. Keyser and Calme (72) combusted sulfur compounds in N2 and then O2 to produce H 2 S 0 4which was conducted through BaC12a t 450 "C to liberate an equivalent amount of HC1, the latter being exchanged for iodine to be titrated with Na2S20,. Singh et al. (73) claimed that a digestion mixture containing K2Cr04,NaOH, and H 2 0 2quantitatively transformed organic sulfur to S042-. Other workers (74, 75) converted the sulfur to SO, which was determined by iodimetry. Special techniques were reported for the determination of sulfur in coals (76),naphthas (77), hydrocarbons containing large amounts of chlorine (78),biological substances (79),plant materials (80),and of sulfur-35 (81, 82). Applying the principles of closed flask combustion and coulometry, Chu et al. (83) fabricated an apparatus for the automated analysis of chlorine, bromine, or iodine; the sample is introduced through a ground-glass connection a t the top of an oval-shape vessel, while the bottom of the vessel is fitted with another ground-glass joint for the insertion of four silver-wire electrodes, two of which serve for electrolysis and two for dead-stop end-point detection. Bigois et al. (84)employed flash combustion at 1050 "C in a vertical tube in a current of oxygen; the gaseous products were swept through silica wool a t 900 "C into the electrolyte and the C1- or Br- was titrated by electrogenerated Ag+ to an amperometric end point. Kowal e t al. (85) recommended decomposition in the presence of platinum a t 1100 "C in a stream of oxygen. Other decomposition techniques include dehalogenation of pesticides by irradiation (86)and of halo-6-diketones by heating in aqueous KI solution a t 40 "C (87). In the closed flask combustion method, Cu(N0J2 was used as absorbent for sulfur-containing
x
mode of finish
.ref.
radioactivity radioactivity atomic absorption radioactivity neutron activation atomic absorption radioactivity colorimetry neutron activation neutron activation colorimetry colorimetry atomic absorption colorimetry polarography atomic absorption X-ray fluorescence colorimetry
330 331 332 33 3 334 335-337 338, 339 340 341,342 343 344 345 346-349 350 351 35 2 353 354
Table 111. Simultaneous Determination of Nonmetallic Elements by Combustion elements determined
combustion products
eo,, N2
c, N
mode of finish
ref.
355
gas chromatography spectroscopic radioactivity, 14C) 35s gavi me try, gasometry
c, N
c, s
H, N
356 351 358 359
N, F N,
s
halogen, S S, Se C, H, S C, H, Se H, N, halogen N, F, C1 (or Br) c , H, N, 0 C, H, N, S C, H, F, Si c , H, c1, s, Hg
N,, HF, HCI (or HBr)
.
gas chromatography titrimetry
360
coulometry gavimetry gravimetry gravimetry, gasometry gas0 metry,
362 363 364, 3 6 5 366
361
3 67 368
gas chromatography gas chromatography gravimetry
369
gravimetry
37 1
370
-
material (88),while EDTA was added to the absorption solution for mercury compounds (89). Determination of chlorine, bromine, or iodine by neutron activation ( g o ) , and of iodine by isotopic exchange (91) were reported. Zarembo e t al. (92, 93) determined fluorine b high resolution NMR which involves integration of the F signal by interfacing with a computer. Noshiro and Yarita (94) converted fluoro compounds to HF by first heating at 600 "C in O2saturated with H20and then on silica at lo00 "C. Volodina et al. (95) liberated NH4F from fluoroborates by heating a t 850 "C in NH , and determined the F by Th(N0J4 titrimetry. Osadchii and haklakova (96) heated the sample with Al13 and determined the AlF, in the volatile reaction products. Debal et al. (97) studied precision colorimetry for fluorine analysis. Other workers determined fluorine by neutron activation (98), photon activation (99),y-ray activation (loo),or cyclic activation (101) techniques.
B
OTHER NONMETALLIC ELEMENTS Volodina e t al. (102) described a method to decompose ANALYTICAL CHEMISTRY, VOL. 52, NO. 5 , APRIL 1980
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ORGANIC ELEMENTAL ANALYSIS
Table IV. Simultaneous Determination of Metals and Metalloids method atomic absorption
atomic emission
biological fish foods p har ma ceut i ca 1 petroleum plants biological foods petroleum plants
neutron activation
elements that can be determined
ref.
Ca, Mg, Cu, Fe, Cd, Zn, Pb, Al, As, Cd, Co, Cr, Mn, Hg, Ni, Au Pb, Cd, Zn, Cu, Se, Hg, As Pb, Zn, Cu, Cd, Fe, Ca, Sb, As, Sn Mn, Cu, Co, Fe, Mo V , Ni Pb, Cd, Cu, Zn, Mn many elements Fe, Cu, Zn B, P, Ca, Hg, Be, Cr, Cu, Mn, Zn, Ag, Al, Fe, Ni, V, Pb, Ti, Si Al, B, Ca, Cd, Co, Cr, Cu, Fe, K, Mg, Mn, Na, P, Pb, Si, Zn Ca, P, K, Al, Na, V, Cu, Mn, As, Se, Fe, Zn, Co, Ag, La, Cd, Hg, Cr,Cs, Rb, Sb, Mo. Te. La. W. Au Hg, As, Cd Mn, Na, K, La, Au, Cr, Fe, Rb, Sc, Cs, Zn, Co, Mg, Mn, Al, Ca, Cu, Hg, Cd, Sn,
377-385
material analyzed
biological
I
fish foods
386-388 389-395 396 397 398,399 400 401 402 403 404-416
,
417 418-420
Sb
petroleum plants photon activation X-ray fluorescence
plants biological foods pharmaceuticals
polarography
vo Ita mmet ry
colorimetry
plants foods pharmaceuticals plants plastics biological foods biological
A< As, Co, Dy, Eu, Fe, La, Mn, Mo, Ni, Na, Se, Sm, V Mg, Si, P, K, Ca, Na, Mn, Zn, Co,Sb, Ba, Cr, Sc, Au, W, As 17 elements Pb, Zn, Cu, Fe, Na, K , Ca, Mn, Ni, As, Se, Rb, Sr, Zr, Mo, Hg, Sc, Ti, V, Cr, Co, Y, Nb Ca, K, P Se, Pb, As, Zn, Cu, Ni, Co, Fe, Hg, Sb K, Ca, Mg, Fe, Cu, Zn, Sr Cu, Zn, Mn, Cd, Pb Fe, Mn, Pb, Cu, Bi, Sn Cu, Pb, Cd, Zn, M o Cu, Fe, Zn Cu, Pb, Cd, Hg, Bi, Sb, Sn, T1, In, Zn Cu, Pb Fe, Cu, Bi
organophosphorus by irradiation, followed by weighing the nonhygroscopic H3P04formed. Osadchii and Maklakova (103) converted organic phosphorus into AlF' by heating the sample with aluminum powder to 500 OC; the A1P was then dissolved in HN03, and the A1 in solution was determined by titration with EDTA. Sliepcevic et al. (104) designed a combustion flask to determine phosphorus in petroleum products by covering the material with Na2C03in a platinum boat. Other workers used acid digestion and colorimetric finish for automated (105) and simplified (106)procedures. Phosphorus was also determined by atomic absorption (107-109), NMR (110), and optical emission (111) spectrometry. Fusion with Mg(N03)2-Mg0 was used in the analysis for arsenic, with colorimetric (112) or atomic absorption (113) finish. Digestion in HN03-HC104 was employed for biological materials, followed by generation of ASH, ( I 14). Similarly, antomony was determined as SbH3 (115). Determination of arsenic by high-speed anodic-stripping voltammetry (116), and by plasma emission spectrometry (117) were proposed. Anisimova and Klimova (118) combusted organoselenium compounds a t 900 OC in 02.The resulting SeOz was trapped in crushed glass moistened with H 2 0 and then dissolved in HN03 and treated with KI to liberate iodine which was reduced with excess Sz02-;the unconsumed S202- was titrated coulometrically with iodine. Selenium in biological materials was determined by atomic absorption spectrometry (119), fluorimetry (120-122), X-ray fluorescence (123), proton-induced X-ray emission (124), neutron activation (125-129), and photon activation (130). Gas chromatography was utilized to determine selenium after suitable derivatization (131-134). Organotellurium compounds were decomposed by heating in HNO and the tellurium was then determined by polaro rap%y (135). Another method employed closed flask comfustion followed by atomic absorption spectrometry (136). For the determination of boron, Debal et al. (137)reported t h a t wet oxidation followed by colorimetry was the most 46R
ANALYTICAL CHEMISTRY, VOL. 52, NO. 5, APRIL 1980
421,422 423-428 429 430-43 2 433 434 435 436-438 439 440-442 443 444-447 448 449,450
satisfactory. Other workers employed ashing a t 450 "C (138) and fluorimetric finish (139). Organosilicon compounds were decomposed by means of low-temperature radio-fre uency-discharge oxygen plasma, producing SiOz which was letermined ravimetrically (140). Up to 50% of fluorine in the sample $id not interfere.
ORGANOMETALLICS Dagaev et al. (141) proposed to analyze organoaluminum compounds by hydrolyzing the sample in 0.5 M HCIOI and, after filtration, titratin the unconsumed HC104 with 0.5 M NaOH potentiometricdy . Aluminum in biological materials could be determined by atomic absorption spectrometry by placing the sample directly into the graphite furance (142), but it was better to add NH3 t o prevent formation of volatile AlC13 (143). For the determination of berylium, ashing followed by extraction as acetylacetonate was recommended (144).
Biological samples for cadmium determination were decomposed by acid digestion, followed by extraction as complexes and atomic absorption spectrometry (145-147) or voltammetry (148). Several automated procedures for determining calcium in biological substances were proposed, using fluorimetric titration (149) or colorimetry (150-152). For the determination of calcium in plant material by atomic absorption spectrometry, Adrian and Stevens (153) found that sample preparation procedures had significant influence on the results. Guthrie et al. (154) reported on the effects of sample volume, charring conditions, type and mode of inert-gas flow, and individual graphite tubes on the background value in the determination of chromium. Copper in gasoline was measured by atomic absorption spectrometry with electrothermal atomization (155). Copper and iron in blood serum were determined by X-ray fluorescence (156). Iron was also determined by an automated
ORGANIC ELEMENTAL ANALYSIS
ferrozine method (157), atomic absorption (158),and colorimetry (159). Campiglio (160) described the analysis of or anolead compounds by potentiometric determination of Pf(I1) with ionselective electrode. Lead in petroleum products was determined by iodine monochloride (161) and voltammetric (162) methods. For the determination of lead in biological samples, colorimetry, atomic absorption (163),and luminescence (164) were employed. Collaborative study of lead determination in foods by atomic absorption spectrometry revealed considerable variations in accuracy and precision (165). Jones and Boyer (166) described a sample-homogenization procedure for canned foods. Amplification reactions based on iodimetry was utilized to analyze organomercury compounds after closed flask combustion (167). Halogenated substances were decomposed by low-temperature oxygen-plasma ( I @ ) , while silicon-containing mercurials were heated in H2S04-KMn04-K2S208 (169), followed by atomic absorption spectrometry. For the determination of mercury in biological materials, atomic absorption spectrometry (170) was shown to be more sensitive than neutron activation analysis (171). Palladium in plant material was determined colorimetrically using nitroso-N-phenyldibenzylamine as reagent (172). Platinum ammine complexes were oxidized by HC104, followed by indirect complexometric titration using EDTA (173). Platinum in DNA-platinum complexes was determined by fluorescence spectrophotometry (174). Tin in organosilicontin compounds was determined by fusion with Na202followed by colorimetry with use of catechol violet (175). Microwave-induced plasma atomic emission spectrometry was employed to determine tin in plant material after acid digestion and hydride generation (176). Titanium in organic derivatives of orthotitanic acid was determined by polarography (177). Organovanadium compounds were decomposed by H2S04-HN03, and the vanadium(V) was determined spectrophotometrically as the yellow tungstovanadophosphate complex (178). Zinc in chelates of Schiff bases was determined by atomic absorption spectrometry by dissolving the sample in dimethylformamide and aspirating the solution into an air-acetylene flame.
TRACE ANALYSIS Selected papers on trace analysis of nonmetals are given in Table I; those on the determination of metallic elements are listed in Table 11. As in the past, these publications reported on the application of the existing techniques for the analysis of a particular element in certain categories of organic material. It will be noted that biological substances were most frequently encountered. Among the metallic elements, those which are health hazards were most intensely studied.
SIMULTANEOUS DETERMINATION OF SEVERAL ELEMENTS Applying the conventional combustion techniques (2) and appropriate methods of measurement, investigators continued to develop procedures with which two or more nonmetallic elements can be determined using a single sample. These publications are summarized in Table 111. Nondestructive methods were also employed for the simultaneous determination of several nonmetallic elements. Thus Glazov (372) determined carbon and oxygen in C-H-0 compounds by means of reflected fl radiation. Henningsen et al. (373) determined carbon and oxygen and other elements by a-induced X-ray spectrometry. Lisovskii and Smakhtin (374) determined chlorine, bromine, and phosphorus in oranophosphorus compounds by neutron activation analysis. hand and Noble (375) described a method for differential measurement of tritium and iodine-125 by liquid scintillation spectrometry. Windsor and Denton (376) evaluated the application of inductively coupled plasma optical emission spectrometry for the determination of carbon, hydrogen, bromine, iodine, sulfur, phosphorus, and silicon. Numerous papers were published on the simultaneous determination of metallic elements in organic materials. As can be seen from Table IV, atomic absorption, radiochemical, and X-ray techniques were in vogue. These methods entail large capital investment and big maintenance costs. Perhaps the less expensive methods like spectrophotometry and po-
8
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Electron Spin Resonance John R. Wasson" and Jorge E. Salinas Ellestad Research Laboratories, Lithium Corporation of America, P.O. Box 795, Bessemer City, North Carolina 280 16
This review covers the published literature from July 1977 to July 1979 although a few citations of other work are also included. Thousands of articles containing ESR information were published during the two-year span covered by this 50 R
0003-2700/80/0352-50R$Ol .OO/O
review ( 1 ) . Hence, no attempt can be made a t inclusive citation, even ever so briefly, in the space available for the present effort. Rather, this review is intended to serve as a guide to the current literature and provide an eclectic selection
0 1980 American
Chemical Society
