Anal. Chem. lQ80, 58,315R-321 R SP22. Lall, R. S. Curr. Sci. 1984, 53,642-643. SP23. Lamparczyk, H. HRC CC, J. High Resoluf. Chromafogr. Chromafogr. Commun. 1985. 8,90-92. SP24. Lamparczyk, H.; Radeckl, A. Chromafographla 1984, 78, 615-618. SP25. Lehtonen, P. Chromafographia 1984, 79, 316-321. SP26. Lurie, IS.; Allen, A.C. J. Chromafogr. 1984,292, 283-294. SP27. Mekenyan, 0.; Balaban, A. T.; Bonchev, D. J. Magn. Reson. 1985,63, 1-13. SP28. Randic, M. J. Chem. Inf. Compuf. Sci. 1084,2 4 , 164-175. SP29. Randic, M.; Kraus, G.A.; Dzonova-Jerman-Blazlc, B. Sfud. Phys. Theor. Chem. 1983, 28 (Chem. Appl. Topol. Graph Theory), 192-205. SP30. Raymer, J.; Wiesler, D.; Novotny, M. J. Chromatogr. 1985, 325, 13-22. SP3I. Razinger, M.; Chretien, J. R.; Dubois, J. E. J. Chem. Inf. Compuf. Scl. 1985, 2 5 , 23-27. SP32. Rohrbaugh, R. H.; Jurs, P. C. Anal. Chem. 1985, 57, 2770-2773. SP33. Sabljic, A. J. Chromafogr., 1984,314, 1-12. SP34. Sabljic, A. J. Chromafogr., 1985,319, 1-8. SP35. Schultz, T. W.; Kier, L. B.; Durnont, J. N. Synfh. Fossll Fuel Technol., Proc. Life Sci. Symp., 5th 1984,373-386. SP36. Slngh, V. K.; Tewari, V. P.; Gupta, D. K.; Srlvastava, A. K. Tetrahedron 1984,40, 2859-2863. SP37. Small, G.W.; Jurs, P.C. Anal. Chem. 1984, 56,1314-1323. SP38. Szasz, G.;Papp, 0.;Vamos, J.; Hanko-Novak, K.; Kier, L. B. J. Chromafogr. lg83,269, 91-95. SP39. Takamoto, S. Talanfa 1985, 3 2 , 757-782. ART1FI C1AL INTELLIGENCE AI1. Adler. B.; Eitner, B.; Herrmann, A,; Sorkau, E. 237-247.
Z. Chem. 1984, 2 4 ,
AI2. Borman, B.A. Anal. Chem. W85, 57,983A-994A. AI3. Dessey, R. Anal. Chem. 1985,57, 1298A-1314A. AI4. Dessey, R. Anal. Chem. 1984, 56, 1200A-1212A. AI5. Dessey, R. Anal. Chem. 1984, 56, 1312A-1332A. AI6. Dubols, J. E.; Sobel, Y. J. Chem. Inf. Compuf. Sei. 1985, 2 5 , 326-333. A17. Dubols, J. E.; Carabedian, M.; Dagane, I.Anal. Chim. Acta 1984, 758, 2 17-233. AI8. Hippe, 2.; Debska, B.; Duliban, J.; Guzowska-Swider,B. Ser. Chem. (Uniw. im Adama Mickiewicza Poznaniu) 1984, 44, 33-51. CA 103, 141 0 3 5 ~ . AI9. Hu, X.; Wang, X. Huaxue Tongbao 1984, 3, 29-32. CA 101, 54052r. AI10. Jamroz, M.; Latek, 2. J. Mol. Sfrucf. lg84, 115, 277-280. AI11. Klaessens, J. W. A,; Katernan, G.; Vandeginste, 6.G. M. TrAC, Trends Anal. Chem. (Pers. Ed.) 1985, 4, 114-117. AI12. Klopman, G. J. Am. Chem. Soc. 1984, 106, 7315-7321. AI13. Lochmueller, C. H.; Lung, K. R.; Cousins, K. R. Anal. Lett. 1985, 78, 439-448. AI14. Lu, P.; Lu, X. Sepu. 1984, 7 , 102-109. CA 103, 115329b. AI15. Lu, P.; Lu, X. Sepu. 1984, 1 , 58-60. CA 703, 98096d. AI16. Lu, P.; Lu, X. J. Chromatogr. 1884,292, 169-188. A I l 7 . Massart, D. L.; DeSmet, M. TrAC, Trends Anal. Chem. (Pers. Ed.) 1985,4, 111-112. AI18. Massart, D. L.; Smeyers-Verbeke J. TrAC, Trends Anal. Chem. (Pers. Ed.) 1985, 4 , 50. AI19. Rosenkranz, H. S.; Mitchell, C. S.; Klopman, G. Mufaf. Res. 1985, 150, 1-1 1. AI20. Salk M.; Parsons, M. Anal. Chem. 1885,57, 715A-727A. AI21. Wipke, W. T.; Rogers, D. J. Chem. Inf. Compuf. Sci. 1984,24, 71-81.
Nuclear Magnetic Resonance Spectrometry John R. Wasson’ SYNTHECO, Inc., 1920 Industrial Pike Road, Gastonia, North Carolina 28052
This review covers the published literature from July 1983 to August 1985 although some citations of other work are also included. As noted in earlier reviews (1) it is impossible to summarize 2 years of NMR literature in so short a space. However, it is hoped that the books, reviews, and various citations will be a useful guide to the reader. The publication Spectroscopy (P.O. Box 50, Springfield, OR 97477; H. W. Lafferty, Ed.) has recently commenced and promises to be of interest and utility in various areas of spectroscopy, including NMR. Noninvasive Medical Imaging, an international journal published by Verlag Chemie Gmbh (Federal Republic of Germany) and Reviews of Magnetic Resonance in Medicine published by Pergamon Press cover specialized applications of NMR. The American Chemical Society has introduced an audiocassette course on “Fourier Transform NMR Spectroscopy”. An extensive “C13 NMR Data Base” has been made available by Science Information Services, Inc., Larchmont, NY,and City Software,Milwaukee, WI, has introduced “The NMR Simulator” for the IBM PC.
BOOKS AND REVIEWS The books on NMR spectrometry (2-39) continue to show the wealth of biological applications, with discussions of NMR imaging becoming more prevalent. Outstanding, lucid presentations of other areas have also received attention. Table I lists review articles. For convenience, the references in Table I are collected separately in the bibliography.
APPARATUS AND TECHNIQUES A teaching experiment demonstrating sensitivity enhancement by signal averaging in pulsed Fourier transform NMR has been presented (40). Integration errors in digitized magnetic resonance spectra have been evaluated (41). A simple method for determination of spin-coupling networks using selective irradiation with multiple quantum filtering has been described (42). Automatic phase correction in magnetic
For biographical material, see review on electron spin resonance. 0003-2700/86/0358-3 15R$O 1.5010
resonance using DISPA has been detailed (43). The proton deuterium COSY technique can be used to edit a 2H N IdR spectrum when overlapping resonances prevent assignment of a one-dimensional spectrum (44). A pulse sequence has been described that facilitates direct measurement in steroids and other molecules of geminal couplings (VHH) containing many methylene carbon atoms without nonequivalent H atoms without resolving the complete homonuclear coupling pattern (45). Steady-state pulse calibration (46), pulse sequences that discriminate between direct and long-range C-H couplings (47),composite pulse sequences with variable performance (&), and a 1-D technique for correlation of proton and carbon chemical shifts (49) have been reported. A pulse sequence for simplifying ‘H NMR spectra of biological tissues has been developed (50). A method for obtaining proton scalar-coupling-correlated 2D spectra in protonated solvents has been presented (51). Optimization of the 2D homonuclear RELAY experiment has been described (52). A pulse sequence has been reported (53) for selectively suppressing I3C lines of nondeuterated solvents in 13C NMR spectra. Selective spin-lattice relaxation time (TJ and transferred nuclear Overhauser effect (NOE) have been used as sensitive methods for detecting binding of ligands to macromolecules,e.g., carbobenzoxyglycine to zinc carboxypeptidase A (54). Relaxation effects on quantitation in 13C NMR spectroscopy were investigated to define prerequisite conditions for obtaining quantiative results efficiently (55). A FORTRAN program for reduction of NMR relaxation data has been described (56). Site-to-site rate constants can be determined from 2D NMR obtained with a program of phase cycling that produces pure absorption-mode spectra in both dimensions (57). A new method for obtaining isotopic fractionation data at multiple sites in rapidly exchanging systems has been described (58). Magic-angle hopping as an alternative to magic-angle spinning for solid-state NMR has been described (59). A method has been reported (60) for obtaining high-resolution NMR images in solids and also one (61) for obtaining ultrahigh-resolution multiple quantum spectra, even in solids. A general method for spatially resolved high-resolution NMR 0 1986 American Chemical Society
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Table I. Reviews topic
ref
introductory material NMR methods and techniques INDOR spin-spin coupling-theory spin-spin coupling-applications the general nuclear spin Hamiltonian 2-D NMR multipulse NMR in liquids mathematical techniques line-broadening influences and line-narrowing techniques in solid state NMR polarized p emitters for NMR probes stochastic NMR spectroscopy liquids oriented molecules mixed liquid crystals pulsed field gradient NMR-liquid state molecular organization 13C NMR multipulse sequence for the analysis of coal and petroleum products 13C CPIMAS NMR spectra isotope effects on I3C NMR shifts and coupling constants heterogeneous systems multiple resonance nuclear shielding-theoretical and physical aspects nuclear spin relaxation in fluids relaxation and molecular orientation spin-spin coupling-mechanisms heterocyclics carbanions methylene monoterpenes biological research conformational analysis rotation about C=C bond in enamines containing N-H bond optically detected magnetic resonance NMR-chiral derivatives NMR-chiral solvating agents NMR-chiral shift reagents analysis using chiral solvating agents organic analytical reagents and their metal complexes P-diketones-structure and hydrogen bonding ligand substitution reactions hydrogenated amorphous silicon complexes of molecular oxygen with organic molecules W e chemical shifts in organic compounds 12STeNMR-organotellurium compounds metal-nonmetal transition alkali metals in nonaqueous solvents solutions of metals in nonaqueous solvents carbon-functional organosilicon compounds silicon-29 NMR 29SiNMR-INEPT and DEPT techniques inorganic and organometallic compounds first transition series nuclei organo-f-element complexes sulfur, selenium, and tellurium-containing ligands analysis of explosives microemulsions solubilization equilibria-surfactants 31Pchemical shifts 31Pspin-spin coupling constants two-dimensional 31PNMR compilation of 31PNMR data multiple quantum NMR macromolecules synthetic macromolecules polymer quantitative analy~is-'~C NMR molecular orientation 316R
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NO. 5,
1 2, 3 4 5 6 7 8 9-1 1 12 13 14 15 16 17 18, 19 20 21 22 23 24
25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46,47 48 49 49 50 51 52 53 54 55 56, 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72
APRIL 1986
topic chain motion in macromolecules macromolecular conformation-13C and 2sSi MAS Deuteron NMR-chain mobility and orientation in polymers microstructure of synthetic polymers lanthanide shift reagents-polymer microstructure thermal degradation studies-polymers cross-linked polymers molecular motion in plastic crystals cross-polarization-magic-angle spinning cellulose ethers CP/MAS NMR-carbohydrates and aromatic polymers rare gas solids rotating superfluid helium-3 spin glasses phase transitions materials science dislocations in solids solid surfaces solids indirect measurement of proton TI relaxation in solids clathrates guest molecules in intercalation compounds graphite intercalation compounds inclusion compounds dynamic nuclear polarization in 13C NMR in solids librational tunneling in some ammonium compounds spin dynamics in one-dimensional systems polymer-supported reagents and catalysts adsorption and catalysis specific adsorption in oxides heterogeneous catalysts physisorbed and chemisorbed species organic compounds adsorbed on porous solids variable-temperature MAS solid-state NMR CH, (n = 0-3) groups in fossil fuel materials coal analysis analysis-petroleum residues crude oil petroleum and coal liquefaction products coal aromaticity heavy fossil fuels small particles decationized and dealuminated zeolites29Siand 27AlNMR zeolites ceramics medical studies biological research natural macromolcules living systems modern NMR-polymers, biochemistry medical uses historical review-clinical applications clinical pathology NMR and the biochemist plant metabolism in vivo protein internal dynamics-solid-state studies olig~saccharides-~~C NMR red seaweed polysaccharides carbohydrate chains of mucin-type glycoproteins antibiotics of the Vancomycin group anomeric configuration of C-nucleosides by 'H NMR and 13C NMR macrolides carbohydrate chemistry arylcyclohexylamines related to phencyclidine Clg-diterpenoid alkaloids
ref 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87, 88 89 90 91, 92 93-100 101 102 103 104 105 106 107 108 109 110,111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128, I29 130 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147
NUCLEAR MAGNETIC RESONANCE SPECTROMETRY
Table I (Continued) topic
ref
topic
ref
bioactive molecules biophysical applications of 1 7 0 NMR in vivo applications in medicine blood and urine analyses diagnostic and investigative medicine clinical applications NMR in cancer-tumors carcinogen-modified DNA model compounds neuropharmacology visual pigments and related systems chlorophylls and corrins food analysis good analysis-seed and flour water determination in the pharmaceutical industry NMR imaging paramagnetic contrast agents paramagnetic pharmaceuticals lanthanide complexes of peptides and proteins iron and gadolinium chelates-NMR contrast agents contrast agents and spectroscopic probes contrast enhancement in biomedical NMR epithelial ions phosphate covalently bound to proteins31P NMR muscle m e t a b ~ l i s m - ~ ~NMR P metabolic appli~ations--'~CNMR enzyme mechanism
148 149 150 151 152 153 154 155 156 157 158 159 160 161
enzyme catalyzed rates of reaction by 2D NMR enzymatic rates in vitro and in vivo by magnetization transfer lipid polymorphism, reverse micelles lipids in biological membranes 2H NMR fluidity of membranes ionic mechanisms and selectivity of the gramicidin transmembrane channel membrane structure-deuterium NMR bile salt micelles water diffusion through erythrocyte membranes dynamic structure of membranes--2H NMR protein structure and funtion muscle proteins 3D structure of noncrystalline polypeptides manganese(I1) carbonic anhydrase copper proteins bilins and bilin-protein linkages in phycobiliproteins enzyme me~hanisms--'~CNMR DNA-conformational states and dynamics 31P-clinical biochemistry cyclic AMP-dependent protein kinase enzyme mechani~ms-~'P and I3C NMR enzyme c~mplexes-~~P NMR chiral thiophosphates and the stereochemistry of enzymatic phosphoryl transfer chiral l60,170, phosphate estersenzymatic phosphoryl transfer reactions "P NMR-metabolic changes at cellular and organ level
174 175
162 163 164 165 166 167 168 169 170 171 172 173
176 177 178 179 180 181 182 183 184 185 186 187 188 189 190 191 192 193 194 195 196 197 198
Table 11. Analytical Applications ref
topic
-
quantitative NMR-theoretical aspects quantitative determination 13C-16N chemical bonds fatty amines and their derivatives by 13C NMR enantiomeric excess by 13C NMR proton relaxation times in normal and pathological tissues-correlation with other tissue parameters proton relaxation times-systemic effect of cancers on human sera pharmaceuticals-quantitative pulsed Fourier transform IH NMR syn-anti isomerism in the opiate hydrazones and azines-'H NMR busu1fan phenylbutazne cloxacillin dicyclomine hydrochloride phenytoin and sodium phenytoin tetracycline antibiotics and their common imp~rities--'~CNMR
1 2
3 4 5
6 7 8 9 10
11 12 13 14
-
spectroscopy has been proposed (62)that permits high-speed spectroscopic study of spatially inhomogeneous objects such as biological systems. Simultaneous measurements of ionic mobilities, transference numbers, and self-diffusion coefficients using an NMR pulsed-gradient have been presented (63). A recycled-flow Fourier transform NMR system has been evaluated (64) for structure analysis utility. A magic-angle spinner for vacuum-sealed samples has been described (65). A furnace has been developed for NMR experiments at 300-1100 K (66). A high-resolution NMR probe in which the coil and preamplifier are cooled with liquid helium has been described (67). Conversion of instrumentation from tap water cooling to cold water recirculators has been described for a Varian A-60A N M R (68). A pulsed NMR thermometer that can operate at several frequencies has been developed (69). A 100-MHz N M R probe head for hydrostatic pressures u p to 200 MPa has been described (70). A NMR probe head for investigations under hydrostatic pressures u p t o 7 kbar has
topic
ref
diethylcarbamazine citrate in tablets by 'H NMR benoxaprofen, nabilone, and cefazolicsolid state 13C NMR propoxur glutathione-intact and hemolyzed erythrocytes soil organic matter maps amber from the Dominican Republic wood and wood p~lping--'~CNMR wood tars-IH NMR and I3C NMR determination of iodine number in base stock lubricants survey of U.S. oil shales optically active perfluroinated compounds p-fluorobenzoyl chloride for characterization of active hydrogen functional groups by lgF NMR fat content in meat products herbaceous plants and their components13C NMR simultaneous determination of moisture and oil content in oilseeds
15 16 17 17a 18 19 20 21 22 23 24 25 26 27 28
been reported (71)as has capillary tude sealing for microcell NMR spectrometry (72). Dy, T b , a n d Yb shift reagents for 39KN M R have been described (73). Dy(II1) and Tm(II1) complexes with tripolyphosphate have been used as shift reagents for 43Ca NMR studies of calcium-binding proteins (74). A gadolinium(II1) P-diketonate has been employed in a simple method for determination of enantiomeric excess (75). A combined search system using IR absorption, 13CNMR, a n d mass spectra has been developed (76). A culture assembly has been described (77) which can be conveniently used in an N M R spectrometer and which supports anchorage-dependent cells for periods as long as 1 month. Anhydrous magnesium chloride in Me2SO-d, and DMF-d, has been employed t o yield phenolic hydroxyl a n d ortho proton shifts to aid signal a n d structural assignments for naturally occurring phenols (78). T h e lanthanide-inducedshift-assisted determination of proton spin-lattice relaxation ANALYTICAL CHEMISTRY, VOL. 58, NO. 5, APRIL 1986
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times has been developed (79). Europium(II1) (R)propylenediaminetetraacetate ion was shown to be a useful chiral shift reagent in the lH NMR spectroscopy of hydroxy, amino, and carboxylic acids in aqueous solution (80).
SPECTRAL ANALYSIS The statistical theory of energy levels or random matrix theory has been presented (81)in the context of the analysis of chemical shifts of spectra of large biological systems. A theoretical and experimental study was made of the relative motion of ions in solution and ex licit calculations were made for model aqueous electrolytes p82). Procedures have been reported (83) for solving eigenvalue-eigenvector problems for A3B, AIB, and more complex many-spin systems with spins of 1 and 312. The NMR shielding constants in Cu, An, Ag, and Cd complexes were studies theoretically using the ab initio finite perturbation SCF method (84). Signal to noise in derived NMR images has been investigated theoretically (85).Decomposition of lH NMR spectra into individual spin multiplets has been achieved by a simple method (86).Two new techniques based on the echo-planar imaging method for spatial mapping of the chemical shift have been presented (87). Hidden assumptions in the average structure method have been explored (88). The nuclear magnetic perturbation-response characteristics of the fourspin AMXz grouping have been derived in detail (89).The complex Ag[Eu(fod),] is a better shift reagent for substituted ammonium halides than lanthanide tris(&diketonates) (90). The 13Cchemical shifts of the halogen-sustituted methanes can be reproduced by a linear two-parameter equation (91). A short set of 13CNMR correlation tables (92),a primer on Fourier transform NMR (93), and an experiment on isomer identification (94) have been given, which are useful for instructional purposes. A table of expectation ranges of 13C NMR chemical shifts has been presented (95).The use of 13C to '?F dipolar couplings as a structural probe has been explored (96). An attached proton test technique for signal enhancement can be applied to systems with long-range heteronuclear couplings in P-O-C-H fragments (97).Assignment of proton NMR spectra and conformational analysis by 2-D heteronuclear relayed correlation NMR have been described for menthol (98). A 13Cspin-echo sequence with a single variable proton pulse coincident with the carbon refocusing pulse has been proposed which provides complete editing of a 13Cspectrum into separate quaternary, methine, methylene, and methyl subspectra (99).A modification of the INADEQUATE NMR experiment has been presented (loo),which can be used to simplify the spectra obtained or establish C-C connectivities in a simple one-dimensional way. Automated procedures have been described (101)for selecting observations to be deleted in the formation of linear models for 13Cchemical shifts of steroids. A simple software mechanism for the assignment of 31PNMR spectra has been described (102).A distance geometry program for determining the structure of small proteins and other macromolecules from NMR measurements of intramolecular proton-proton proximities in solution has been developed (103). Computer simulations of multiple-quantum NMR experiments, previously analyzed by coherent averaging theory, have been reported (104). Calculator programs for ABX analyses have been described (105). The FORTRAN program NMRSP for simulation of high-resolution NMR spectra showing fiiite passage effects has been reported (106).
SELECTED SYSTEMS HCN has been examined in various liquid crystal solvents (107)and HCN polymerization explored (108).A 2-D NMR study of decaborane has been reported (109).The "0 NMR spectra of esters have been correlated with 13C NMR and IR spectral data (110). A number of safe common agents for NMR contrast have been evaluated for human NMR imaging studies (111). Noninvasive study of high-energy metabolism in human heart by depth-resolved 3PNMR (112)and highresolution lH NMR analysis of metastatic cancer cells (113) have been reported. The solid polypeptides (chymotrypsin, insulin, lysozyme, and RNase A) have been examined by proton relaxation (114). A CP-MAS NMR study of some deactivation methods in capillary gas chromatography has been reported (115).Relationships of the 15NNMR chemical shift to the lsN-lH spin coupling constant to the IR stretching 318R
ANALYTICAL CHEMISTRY, VOL. 58, NO. 5, APRIL 1986
frequency of the amino group in saturated primary amines and anilines have been described (116). More properly analytical applications of NMR are collected in Table 11.
ACKNOWLEDGMENT The author is grateful to G. Foltz and Joann n u l l , Lithium Corporation of America, for use of library facilities. LITERATURE CITED (1) Wasson, J. R. Anal. Chem. 1984, 56, 212R-219R. (2) Oki, M. "Applications of Dynamic NMR Spectroscopy"; VCH Publ.: Deerfieid Beach, FL, 1985. (3) Emsiey, J. E., Ed. "NMR of Liquid Crystals"; Reidel: Boston, MA, 1985. (4) Ando, I.; Webb, G. "Theory of NMR Parameters"; Academic Press: Orlando, FL, 1984. (5) Emsley, J. W., Ed. "Progress in NMR Spectroscopy"; Pergamon Press: New York, 1984; Vol. 15. (6) Brocas, J.; et al. "The Permutational Approach to Dynamic Stereochemistry" McGraw-Hili: New York, 1983. (7) Levy, G. C., Ed. "Topics in C-13 NMR Spectroscopy"; Wiley: New York, 1984; Vol. 4. (8) Waugh, J. S.,Ed. "Advances in Magnetic Resonance"; Academic Press: Orlando, FL, 1983, Vol. 11. (9) Schultz, H. D., Ed., "Coal Liquifaction Products. Vol. 1. NMR Spectroscopic characterization and Product Processes"; Wiiey: New York, 1983. (10) Podo, F., Orr, J. S., Eds. "Identification and Characterlzation of Bioiogical Tissues by NMR"; lst, Super, Sanita: Rome, Italy, p 984. (11) Webb, G. A., Ed. "Specialist Periodlcal Reports. NMR", Royal SOC. Chem.: London, 1983; Voi. 12. (12) Petrakis, L., Fraissard, J. P. Eds. "Magnetic Resonance-Introduction, Advanced Topics and Applications to Fossil Energy"; Reidel: Hlngham, MA, 1984. 13) Shaw, D. "Fourier Transform NMR Spectroscopy", 2nd ed.; Elsevier: New York, 1984. 14) Webb, G. A., Ed. "Annual Reports on NMR Spectroscopy"; Academic Press: New York, 1985; Vol. 16. 15) Gorenstein, D. G., Ed., Phosphorus-31 NMR. Principles and Applications"; Academic Press: Orlando, FL, 1984. 16) Breltmaier, E.; Bauer, G. "C-13 NMR Spectroscopy-a worklng manual wlth exercises"; Harwood: New York, 1984. 17) Webb, G. A., Ed. "Nuclear Magnetic Resonance"; Royal SOC.Chem.: London, 1984; Vol. 14. 18) Richards, W. G.; Scott, P. R. "Structure and Spectra of Molecules"; Wiley: Somerset, NJ, 1985. 19) Gerstein, B. C.; Dybowski, C. R. "Transient Techniques in NMR of Soilds"; Academic Press: Orlando, FL, 1985. (20) Asahi Resarch Center Co., Ltd., Japan, Ed. "Handbook of Proton-NMR Spectra and Data"; Academic Press: Orlando, FL, 1985; 5 volumes. (21) Coyie, J. D.; Haws, E. J.; Miller, K.; Norton, K. "Interpretation of NMR Spectra-An introductory Audlovisual Program"; Wiiey: New York, 1984. (22) Abragam, A. "Principles of Nuclear Magnetism"; Oxford Universlty Press: New York, 1983. (23) Pham, 0. T.; Petiaud, R.; Waton, H. "Proton and Carbon NMR Spectra of Polymers"; Wiiey: New York, 1983; Vol. 2. (24) Pham, Q. T.; Petiaud, R.; Liauro, M. F.; Waton, H. "Proton and Carbon NMR Spectra of Polymers"; Wiiey: New York, 1984; Voi. 3. (25) Kausch, H. H., Zachmann, H. G. Eds. "Advances In Polymer Science. Vol. 66. Characterization of Polymers in the Solid State"; Springer-Verlag: Berlln, Fed. Rep. Ger., 1984. (26) Beall, P. T.; Amtey, S. R.; Kasturi, S. R. "NMR Data Handbook for Biological Applications"; Pergamon: New York, 1984. (27) Webb, G. A., Ed., "Annual Reports on NMR Spectroscopy"; Academic Press: Orlando, FL, 1984; Vol. 15. (28) Mehring, H. "Principles of Hlgh Resolution NMR in Solids"; SpringerVerlag: New York, 1982. (29) Hopf, M. A., Smith, F. W., Eds. "Magnetic Resonance in Medicine and Biology"; Karger: Basel, 1984. (30) Laszlo, P., Ed., "NMR of Newly Accessible Nulcei"; Academic Press: Orlando, FL, 1983 (Vol. 1); 1984 (Voi. 2). (3 1) Bax, A. "Two-Dimensional NMR in Liquids"; Reidel: Dordrecht, Holland, 1982. (32) Sohar, P. "NMR Spectroscopy"; CRC Press: Boca Raton, FL, 1983; Vol. 1 & 2. (33) Lambert, J. B., Riddell, f. G., Eds. "The Multinuclear Approach to NMR Spectroscopy"; Reidel: Boston, MA, 1983. (34) Harris, R. K., "NMR Spectroscopy-A Physico-Chemical View"; Pltman .. Books: -London, 1983. ' (35) Elving, P. J., Bursey, M. M., Koithoff, I.M., Eds. "Treaties on Analytical Chemistry. 2nd Edn. Part 1. Theory and Practice. Vol. 10, Sect. 1. Maanetlc Fieid and Related Methods of Analysis": Wiley Intersclence: New York, 1983. (36) Morris, P. G. "Nuclear Magnetic Resonance Imaging in Medicine and Biology"; Oxford University Press: London, 1986. (37) Roth, K. "NMR-Tomography and Spectroscopy in Medicine"; Springer-Verlag: Berlin, 1984. (38) Evans, E. A.; Warreli, D. S.; Eividge, J. A.; Jones, J. R. "Handbook of Tritium NMR Spectroscopy and Applications"; Wiley: New York, 1985. (39) "Proton NMR Collectlon: 1981-1984, Supplementary Numerical Molecular Weight Index"; Sadtler Research Laboratories: Philadelphia, PA, 1984. (40) Rabenstein, D. L. J. Chem. Educ. 1984, 6 7 , 909-13. (41) Herring, F. H.;Phillips, P. S. J. Magn. Reson. 1985, 62, 19-28. (42) Bolton, P. H. J. Am. Chem. SOC.1984, 706, 4299-300.
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Gas Chromatography Ray E. Clement* Ontario Ministry of the Environment, Laboratory Services Branch, P.O. Box 213, Rexdale, Ontario, Canada M9W 5Ll
Francis I. Onuska National Water Research Institute, Canada Centre for Inland Waters, Burlington, Ontario, Canada L9R 4A6
Frank J. Yang Walnut Creek Division, Varian Instrument Group, Walnut Creek, California 94598
Gary A. Eiceman Department of Chemistry, New Mexico State University, Las Cruces, New Mexico 88003
Herbert H. Hill, Jr. Department of Chemistry 4630, Washington State University, Pullman, Washington 99164
INTRODUCTION This review of fundamental developments in the field of gas chromatography (GC) covers the years 1984-1985. The principal method of literature review was by use of the biweekly Chemical Abstracts Service CA Selects for GC. Some publications occurring late in 1983 and not referenced in the previous review of this series (1A) are also included here. Format changes have been introduced to acknowledge recent trends in GC development. Inorganic GC is not included as a separate section. Several extensive reviews of this area have appeared elsewhere (2A-4A). Stronger emphasis is placed on fundamental developments, and previous applications-oriented sections have been dropped. Other sections were combined to eliminate overlapping coverage, and more prominent treatment of supercritical fluid chromatography is given because of the many new developments in this rapidly growing area.
COLUMN THEORY AND TECHNIQUES The general theory is presented for coupled columns of any type that allows calculation of all necessary data for opti0003-2700/86/0358-321R$06.50/0
mization of relative lengths on the basis of readily determined quantities. This procedure requires one to optimize separations via the window analytical technique according to Purcell and Williams (1B). Golovnya (2B) described generally applicable equations for retention data as functions of numerical parameters and homologues. Jennings reviewed gas chromatographic theory (3B). Fernandez-Sanchez (4B)evaluated the liquid loading in GC packings by an extraction method. Kazuma (5B) examined effects of pore diameter on diffusive sample retention. As the ratio of the mean free path of the carrier gas to the pore diameter of the packing gets larger, the diffusive sample retention becomes more effective. Toth and Zala (6B) proposed new equations for the calculation of constants of the logarithmic adjusted retention times vs. carbon number function for consecutive homologous series. Nguyen (7B) proposed application of the Fraser-Suzuki function for the calculation of statistical moments of gas chromatographic curves. The influence of the integration limits on the statistical moments was examined. Berezkin and Retunsky (8B)derived a modified equation for the calculation of theoretical plate number and sorbent selection on the basis of retention indices. Dondi (9B) studied the EdgeworthCramer series peak handling method to detect the onset of 0 1986 American Chemical Society
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