Acetone chemical ionization mass spectrometry

Mass Spectrometry Reviews

Volumn 16, Issue 5, 1997, Pages 259-281

  Prabhakar, S ^a   Vairamani, M ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001228658     PISSN: 02777037     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2787(1997)16:5<259::AID-MAS2>3.0.CO;2-G     Document Type: Article

References (106)

1. Albert, A.; Serjeant, E. P. In Ionization Constants of Acids and Bases; Methuen: London, 1962, pp. 128-131.
2. Benezra, S. A.; Bursey, M. M. "Steric inhibition of gaseous ionic acetylation," J. Am. Chem. Soc. 1972, 94, 1024.
3. Budzikiewicz, H. "Studies in CI mass spectrometry. XI. Structure elucidation by ion-molecule reactions in the gas phase: the location of carbon, carbon-double and triple bonds," Fresenius's. Anal. Chem. 1985, 321, 150-158.
4. Budzikiewicz, H.; Djerassi, C.; Williams, D. H. In Mass Spectrometry of Organic Compounds; Holden-Day: San Francisco, 1967, pp. 94-128.
5. Burinsky, D. J.; Campana, J. E. "Gas phase electrophilic addition reactions of chlorinated alkyl ions," Org. Mass Spectrom. 1988, 23, 613-619.
6. Burinsky, D. J.: Campana, J. E.; Cooks, R. G. "Biomolecular condensation reactions in the gas phase. The schiff base synthesis," Int. J. Mass Spectrom. Ion Proc. 1984, 62, 303-315.
7. Bursey, M. M.; Elwood, T. A.; Hoffman, M. K.; Lehman, T. A.; Tesarek, J. M. "Analytical ion cyclotron resonance spectromelry. Acetylation as a chemical ionization technique," Anal. Chem. 1970, 42, 1370-1374.
8. Bursey, M. M.; Hass, J. R.; Stern, R. L. "Stereospecific reactivity by ion cyclotron resonance spectrometry: Optimization of reactivity differences in two isomeric esters," Anal. Chem. 1975, 47, 1452-1455.
9. Bursey, M. M.; Hoffman, M. K. "An approach to stereochemical analysis by ion cyclotron resonance. Distinguishing exo- and endo-norborneol," Can. J. Chem. 1971, 49, 3395-3398.
10. Bursey, M. M.; Kao, J.; Henion, J. D.; Parker, C. E.; Huang, T. S. "Analytical ion cyclotron resonance spectrometry. Stereochemical effects in some cyclic ketones," Anal. Chem. 1974, 46, 1709-1712.
11. Catalan, J.; Mo, O.; Perez, P.; Yanez, M. "Proton affinities and preferred protonation sites in 3- and 4-substituted pyridines. Prediction from 1s orbital energies," J. Am. Chem. Soc. 1979, 101, 6520-6524.
12. Chatfield, D. A.; Bursey, M. M. "The acetylation of some monosubstituted oxygen- and halogen-containing aromatic compounds by gaseous ions derived from acetone and 2,3-butanedione," Int. J. Mass Spectrom. Ion Phys. 1975a, 18, 239-248.
13. Chatfield, D. A.; Bursey, M. M. "Gaseous ionic acetylation of cresols," J. Am. Chem. Soc. 1975b, 97, 3600-3603.
14. Chatfield, D. A.; Bursey, M. M. "The acetylation of some aromatic compounds containing nitrogen substituents using gaseous ions derived from acetone and 2,3-butanedione," Int. J. Mass Spectrom. Ion Phys. 1976a, 20, 101-106.
15. Chatfield, D. A.; Bursey, M. M. "Rates of gas-phase ionic acetylation of some alkylbenzenes by acetyl cations formed from acetone and butane-2,3-dione," J. Chem. Soc. Faraday Trans, 1 1976b, 72, 417-421.
16. Chatfield, D. A.; Bursey, M. M. "Gaseous ion acetylation of some substituted anisoles. Evidence for an intermediate π-complex," J. Am. Chem. Soc. 1976c, 98, 6492-6495.
17. Clemens, D.; Munson, B. "Selective reagents in chemical ionization mass spectrometry: Trimethylsilyl adduct ions," Anal. Chem. 1985, 57, 2022-2027.
18. +," Org. Mass Spectrom. 1978, 13, 158-162.
19. Cooks, R. G.; Patrick, J. S.; Kotiaho, T.; McLuckey, S. A. "Thermochemical determinations by kinetic method," Mass Spec. Rev. 1994, 13, 287-339.
20. Cope, A. C.; Peterson, P. E. "Proximity effects. XVII. Products and rates of solvolysis of cyclooctenyl derivatives," J. Am. Chem. Soc. 1959, 81, 1643-1650.
21. Daishima, S.; Iida, Y. "Chemical ionization mass spectra of nitrogen heteroaromatics," Shitsuryo Bunseki 1983, 31, 281-287.
22. Denisov, Y. V.; Puchkov, V. A.; Vul'fon, N. S.; Agadzhanyan, T. E.: Antonov, V. K.; Shemyakin, M. M. "Massspectrometric study of the transannular amide-amide reaction with cyclopeptides" Zh. Obshch. Khim. 1968, 38, 770-776.
23. Dixon, W. T.; Murphy, D. "Determination of acid dissociation constants of some phenol radical cations," J. Chem. Soc. Faraday Trans. 2 1978, 74, 432-439.
24. Dzidic, I.; McCloskey, J. A. "Influence of remote functional groups in chemical ionization mass spectra of longchain compounds," J. Am. Chem. Soc. 1971, 93, 4955-4956.
25. Eberlin, M. N.; Cooks, R. G. "Gas-phase oxirane addition to acylium ions on reaction with 1,3-dioxolanes elucidated by tandem and triple stage mass spectrometric experiments," Org. Mass Spectrom. 1993, 28, 679-687.
26. Eliel, E. L. In Stereochemistry of Carbon Compounds; McGraw-Hill: New York, 1962, pp. 253-265.
27. Ferrer - Correia, A. J. V.; Jennings, K. R.; Sharma, D. K. S. "The use of ion-molecule reactions in the mass spectrometric location of double bonds," Org. Mass Spectrom. 1976, 11, 867-872.
28. Fetchtner, T. W.; Winnik, B.; Tevesz, M. J. S. "Gas phase reactions of 1,2:5,6-di-O-isopropylidine-α-D-gluco and allofuranose with electrophiles derived from acetone," J. Carbohydr. Chem. 1996, 15, 1147-1159.
29. Field, F. H. "Chemical ionization mass spectrometry. XII. Alcohols," J. Am. Chem. Soc. 1970, 92, 2672-2676.
30. +," J. Mass Spectrom. 1996, 31, 1086-1092.
31. Gaffney, J. S.; Pierce, R. C.; Friedman, L. "Ammonia chemical ionization of some free amino acids and underivatized peptides," Int. J. Mass Spectrom. Ion Phys. 1977, 25, 439-454.
32. Greco, F.; Liguori, A.; Sindona, G.; Uccella, N. "Gas phase proton affinities of deoxyribonucleosides and related nucleobases by fast atom bombardment tandem mass spectrometry," J. Am. Chem. Soc. 1990, 112, 9092-9096.
33. Gulacar, F. O.; Mermoud, F.; Winkler, F. J.; Buchs, A. "Ammonia chemical ionization mass spectrometry of alcohols: structural, stereochemical, molecular size and temperature effects," Helv. Chim. Acta. 1984, 67, 488-501.
34. Harrison, A. G. In Chemical Ionization Mass Spectrometry; CRC Press: Boca Raton, Florida, 1983, pp. 63-127.
35. Hass, J. R.; Nixon, W. B.; Bursey, M. M. "Acetylation as a chemical ionization technique in medium-pressure chemical ionization mass spectrometry," Anal. Chem. 1977, 49, 1071-1073.
36. Hedin, P. A.; Phillips, V. A. "Chemical ionization (methane) mass spectrometry of sugars and their derivatives," J. Agric. Food Chem. 1991, 39, 1106-1109.
37. Henion, J. D.; Kao, J.; Nixon, W. B.; Bursey, M. M. "Analytical ion cyclotron resonance spectrometry increased discrimination between stereoisomers by ion-molecule reaction with 1,2-dicyclopropylethanedione," Anal. Chem. 1975, 47, 689-692.
38. Henion, J. D.; Sammons, M. O.; Parker, C. E.; Bursey, M. M. "Failure of fundamental rate constant expressions for the gaseous ionic acetylation of 2-alkylpyridines," Tet. Lett. 1973, 49, 4925-4928.
39. Herzschuh, R.; Epsch, K. "Analysis of hydrocarbons by mass spectrometry. V. Relation of electron-induced fragmentation of monocyclic hydrocarbons to ring size," J. Prakt. Chem. 1980, 522, 21-27.
40. Hoffman, M. K.; Elwood, T. A.; Lehman, T. A.; Bursey, M. M. "Mechanism of acetyl transfer to oxygen bases in ion-molecule reactions of 2,3-butanedione," Tet. Lett. 1970, 4021-4024.
41. Hoke, S. H., II; Yang, S. S.; Cooks, R. G.; Hrovat, D. A.; Borden, W. T. "Proton affinities of free radicals measured by the kinetic method," J. Am. Chem. Soc. 1994, 116, 4888-4892.
42. Hop, C. E. C. A.; Dakubu, M.; Holmes, J. L. "Do the aminopyridine molecular ions display aniline- or pyridinetype behaviour?" Org. Mass Spectrom. 1988, 23, 609-612.
43. Horton, D.; Wander, J. D.; Foltz, R. L. "Analysis of sugar derivatives by chemical ionization mass spectrometry," Carbohydr. Res. 1974, 36, 75-96.
44. Hunt, D. F.; Harvey, T. M.; Brumley, W. C.; Ryan, J. F., III; Russel, J. W. "Nitric oxide chemical ionization mass spectrometry of alcohols," Anal. Chem. 1982, 54, 492-496.
45. Hunt, D. F.; Ryan, J. F., III. "Chemical ionization mass spectrometry studies. I. Identification of alcohols," Tet. Lett. 1971, 4535-4538.
46. + with alcohols," Spectroscopy 1987, 5, 111-116.
47. Jalonen, J.; Taskinen, J. "Organic chemistry of gas-phase ions. Part 1. Effect of the protonation site in stereoisomeric norbornenols," J. Chem. Soc. Perkin Trans 2 1985, 1833-1838.
48. Jelus, B.; Dalrymple, D. L.; Michnowicz, J.; Munson, B. "Chemical ionization mass spectra of some 2-norbornyl derivatives," Org. Mass Spectrom. 1978, 13, 163-166.
49. Jennings, K. R. In Gas Phase Ion Chemistry, Vol. 2, Bower, M. T., Ed.; Academic Press: New York, 1979, pp. 124-151.
50. Joutsiniemi, K.; Vainiotalo, P.; Morgenstern, O.; Klemann, A. "Mass spectrometric behaviour of 1 -imino-substituted pyrazolo [1,2-a]-[1,2,4]triazoles under electron and chemical ionization," J. Heterocyclic Chem. 1997, 34, 381-384.
51. Kamar, A.; Young, A.B.; March, R. E. "A comparative ion chemistry study of acetone, diacetone alcohol, and mesityl oxide," Can. J. Chem. 1986, 64, 1979-1988.
52. Kao, J.; Simonton, C. A., III; Bursey, M. M. "Analytical ion cyclotron resonance spectrometry. Stereochemical factors and a functional group interaction in some norbornyl systems," Org. Mass Spectrom. 1976, 11, 140-147.
53. Keough, K.; DeStefano, A. J. "Factors affecting reactivity in ammonia chemical ionization mass spectrometry," Org. Mass Spectrom. 1981, 16, 527-533.
54. Kiryushkin, A. A.; Fales, H. M.; Axenrod, T.; Gilbert, E. J.; Milne, G. W. A. "Chemical ionization mass spectrometry of complex molecules VI. Peptides," Org. Mass Spectrom. 1971, 5, 19-31.
55. Larson, J. W.; McMahon, T. B. "Formation, thermochemistry and related stabilities of proton-bound dimers of oxygen n-donor bases from ion cyclotron resonance solventexchange equilibria measurements," J. Am. Chem. Soc. 1982, 104, 6255-6261.
56. Lee, E. P. F.; Dyke, J. M. "Ab initio molecular orbital calculations on the protonation of acetone monomer and dimer," J. Chem. Soc. Faraday Trans. 1992, 88, 2111-2119.
57. Lehtela, P.; Smolander, R.; Vainiotalo, P. "Mass spectrometric behaviour of simple oxazolidines under electron impact and chemical ionization," Org. Mass Spectrom. 1994, 29, 647-653.
58. Leinonen, A.; Vainiotalo, P. "Chemical ionization mass spectra of simple 1,3-dioxolanes and their sulphur analogues recorded with methane, isobutane, ammonia and acetone as reagent gas," Org. Mass Spectrom. 1994, 29, 295-302.
59. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. "Gas-phase ion and neutral thermochemistry," J. Phys. Ref. Data 1988, 17, Suppl 1.
60. Lias, S. G.; Liebman, J. F.; Levin, R. D. "Evaluated gas phase basicities and proton affinities of molecules; Heats of formation of protonated molecules," J. Phys. Chem. Ref. Data 1984, 13, 695-808.
61. 11SH," J. Am. Chem. Soc. 1974, 96, 359-364.
62. Lide, D. R. In Handbook of Chemistry and Physics, 74th Edition; CRC Press; Florida, 1993, 9-42 to 9-50.
63. Lossing, F. P.; Holmes, J. L. "Stabilization energy and ion size in carbocations in the gas phase," J. Am. Chem. Soc. 1984, 106, 6917-6920.
64. Maquestiau, A.; Flammang, R.; Nielsen, L. "A study of some cations formed in the ammonia chemical ionization of ketones using mass analysed ion kinetic energy spectrometry," Org. Mass Spectrom. 1980, 15, 376-379.
65. March, R. E.; Young, A. B. "An investigation of the structures of isomeric ions derived from acetone, diacetone alcohol, and mesityl oxide," Can. J. Chem. 1988, 66, 591-597.
66. Meot-Ner, M. "Ion thermochemistry of low-volatility compounds in the gas phase 2. Intrinsic basicities and hydrogen-bonded dimers of nitrogen heterocyclics and nucleic bases," J. Am. Chem. Soc. 1979, 101, 2396-2403.
67. Meot-Ner, M.; Field, F. H. "Chemical ionization mass spectrometry XX. Energy effects and virtual ion temperature in the decomposition kinetics of amino acids and amino acid derivatives," J. Am. Chem. Soc. 1973, 95, 7207-7211.
68. Milne, G. W. A.; Axenrod, T.; Fales, H. M. "Chemical ionization mass spectrometry of complex molecules IV. Aminoacids," J. Am. Chem. Soc. 1970, 92, 5170-5175.
69. Munson, B.; Feng, T.; Ward, H. D.; Murray, R. K., Jr. "Isobutane chemical ionization mass spectra of unsaturated alcohols," Org. Mass Spectrom. 1987, 22, 606-609.
70. Munson, M. S. B.; Field, F. H. "Chemical ionization mass spectrometry. I. General introduction," J. Am. Chem. Soc. 1966, 88, 2621-2630.
71. Nakata, H.; Hoshino, Y.; Takeda, N.; Tatematsu, A. "Ammonium adduct ion in ammonia chemical ionization mass spectrometry. 2. Mechanism of elimination of neutrals from the ammonium adduct ion," Org. Mass Spectrom, 1985, 20, 467-470.
72. Pachuta, S. J.; Isern-Flecha, I.; Cooks, R. G. "Charge stripping and the site of cationization of substituted aromatic compounds," Org. Mass Spectrom. 1986, 21, 1-5.
73. Pakarinen, J. M. H.; Vainiotalo, P. "The protonation site of 2-methoxyethanol under chemical ionization: An experimental and theoretical study," Rapid Commun. Mass. Spectrom. 1996, 10, 1901-1904.
74. Partanen, T.; Vainiotalo, P.; Stajer, G.; Bernath, G.; Pihalaja, K. "Electron and chemical ionization mass spectrometry in stereochemical differentiation of some 1,3-amino alcohols," Org. Mass Spectrom. 1994, 29, 126-132.
75. Pearson, R. G. "Hard and soft acids and bases," J. Am. Chem. Soc. 1963, 85, 3533-3539.
76. Podda, G.; Maccioni, A.; Daolio, S.; Traldi, P. "Mass spectrometric synthesis II. The reaction of catechol with acetone in a protic medium," J. Heterocyclic Chem. 1984, 21, 557-560.
77. Pykalainen, M.; Vainiotalo, A.; Pakkanen, T. A.; Vainiotalo, P. "Ion-molecule reactions of simple amines with carbonyl compounds in the gas phase. An experimental and theoretical study of enamine formation," J. Mass Spectrom. 1996, 31, 716-726.
78. Rice, J. M.; Dudek, G. O. "Mass spectra of nucleic acid derivatives II. Guanine, adenine and related compounds," J. Am. Chem. Soc. 1967, 89, 2719-2725.
79. Rice, J. M.; Dudek, G. O.; Barber, M. "Mass spectra of nucleic acid derivatives pyrimidines," J. Am. Chem. Soc. 1965, 87, 4569-4575.
80. Roussis, S. G.; Fedora, J. W. "Determination of alkenes in hydrocarbon matrices by acetone chemical ionization mass spectrometry," Anal. Chem. 1997, 69, 1550-1556.
81. + ions formed from different neutral species," Org. Mass Spectrom. 1981, 16, 393-396.
82. Srinivas, R.; Vairamani, M.; Vishwanadha Rao, G. K.; Mirza, U. A. "Acrylonitrile: A new chemical ionization reagent," Org. Mass Spectrom. 1989, 24, 435-438.
83. + chemical ionization conditions," Org. Mass Spectrom. 1984a, 19, 363-369.
84. + under chemical ionization conditions. 1. Formation of protonated unsubstituted imines," Org. Mass Spectrom. 1981, 16, 45-47.
85. Tabet, J. C.; Tondeur, Y.; Hirano, Y.; Wegmann, A.; Tecon, P.; Djerassi, C. "Ion-molecule reaction in the gas phase. 4. Stereospecific nucleophilic substitution under ammonia chemical ionization conditions from diastereomeric methyl and benzyl ethers of 3-hydroxy steroids," Org. Mass Spectrom. 1984b, 19, 473-481.
86. Tsang, C. W.; Harrison, A. G. "Chemical ionization of amino acids," J. Am. Chem. Soc. 1976, 98, 1301-1308.
87. Tu, Y.; Chen, Y.; Wu, L. "CI mass spectra of substituted phenols with acetone as reagent," Org. Mass Spectrom. 1989, 24, 285.
88. Turecek, F.; Smutek, M.; Hanus, V. "Elimination of water from the molecular ion of cyclohexanol," Org. Mass Spectrom. 1981, 16, 483-489.
89. Ulrich, J.; Teould, R.; Massot, R.; Cornu, A. "Mass spectrometric study of the fragmentation of uracil and thymine derivatives," Org. Mass Spectrom. 1969, 2, 1183-1199.
90. Vairamani, M. "Nitromethane as a substitute for nitric oxide in chemical ionization," Org. Mass Spectrom. 1990, 25, 271-273.
91. Vairamani, M. "Acetone chemical ionization studies. VII. Acetylation of some aromatic compounds," Org. Mass Spectrom. 1993, 28, 1498-1503.
92. Vairamani, M.; Mirza, U. A.; Srinivas, R. "Unusual positive ion reagents in chemical ionization mass spectrometry," Mass Spectrom. Rev. 1990, 9, 235-238.
93. Vairamani, M.; Prabhakar, S.; Prasada Raju, N.; Vishwanadha Rao, G. K. "Acetone chemical ionization studies. VIII. Pyridine derivatives," Eur. Mass Spectrom. 1995, 1, 539-543.
94. Vairamani, M.; Rajeev, M. S.; Siva Kumar, K. V. "Transannular interaction in the gas phase," Rapid Commun. Mass Spectrom. 1991, 5, 35-36.
95. + under chemical ionization," Org. Mass Spectrom. 1992, 27, 57-58.
96. Vairamani, M.; Saraswathi, M.; Siva Kumar, K. V. "Acetone chemical ionization studies III. Displacement reactions in alkyl acetates," Org. Mass. Spectrom. 1992, 27, 27-30.
97. Vairamani, M.; Siva Kumar, K. V. "Acetone chemical ionization studies VI: Hexenyl acetates," Org. Mass Spectrom. 1993, 28, 689-692.
98. Vairamani, M.; Siva Kumar, K. V.; Vishwanadha Rao, G. K. "Acetone chemical ionization studies: Olefines," Org. Mass Spectrom. 1990, 25, 363-367.
99. Vairamani, M.; Siva Kumar, K. V.; Vishwanadha Rao, G. K. "Acetone chemical ionization studies: Part IV. Alcohols," Indian J. Chem. 1992, 31B, 9-14.
100. Vairamani, M.; Srinivas, R.; Vishwanadha Rao, G. K. "Ethylene glycol: A chemical ionization reagent," Ind. J. Chem. 1988, 27B, 264-265.
101. + ions from substituted pyridines by collisionally activated dissociation mass spectrometry," Org. Mass Spectrom. 1983, 18, 331-334.
102. Vogel, P. In Carbocation Chemistry Vol. 21; Elsevier: Amsterdam, 1985, pp. 225-321.
103. Wang, G.; Sha, Y.; Xu, Z.; Pan, J. "Acetone chemical ionization mass spectrometry of monosaccharides," Anal. Chem. 1985, 57, 2283-2286.
104. Winkler, F. J.; Gulacar, F. O.; Mermound, F.; Buchs, A. "Temperature dependence of the isobutane chemical ionization mass spectra of open-chain and cyclic alcohols; Structural, stereochemical and molecular size effects. A revaluation of the isobutane chemical ionization of alcohols," Helv. Chim Acta. 1983, 66, 929-942.
105. Wilson, M.S.; McCloskey, J. A. "Chemical ionization mass spectra of nucleosides. Mechanisms of ion formation and estimations of proton affinities," J. Am. Chem. Soc. 1975, 97, 3436-3444.
106. Wood, K. V.; Burinsky, D. J.; Cameron, D.; Cooks, R. G. "Site of gas-phase cation attachment. Protonation, methylation and ethylation of aniline, phenol, and thiophenol," J. Org. Chem. 1983, 48, 5236-5242.