Abstract
Peculiarities of interaction of H+, Me3C+, and Me3Si+ ions with functional groups of molecules in the gas phase have been studied. Proton tends to form chelates with virtually all of the functional groups studied, whereas Me3Si+ ions exhibit no capacity for chelation. Using isomeric xylenes as examples it was shown that Me3Si+ ions (unlike Me3C+ ions) experience virtually no steric hindrance when they react with nucleophilic centers. Effects of functional groups present in molecules of nitriles on the generation of [M+Me3C]+ adducts in the gas phase and the Ritter reaction in solution were estimated.
Similar content being viewed by others
References
V. I. Kadentsev, D. Sc. (Chem.) Thesis, N. D. Zelinsky Institute of Organic Chemistry of the RAS, Moscow, 1990 (in Russian).
J. Winkler and F. W. McLafferty,Tetrahedron, 1974,30, 71.
K. P. Lim and F. W. Lampe,Int. J. Mass Spectrom. and Ion Phys., 1989,92, 53.
C. A. Maryanoff, G. W. Coldwell, and Y. Chang,Org. Mass Spectrom., 1988,23, 129.
V. I. Kadentsev, L. I. Belen'kii, N. G. Kolotyrkina, and O. S. Chizhov,Izv. Akad. Nauk SSSR, Ser. Khim., 1982, 85 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1982,31, 72 (Engl. Transl.)].
V. I. Kadentsev, A. V. Krokhin, O. S. Chizhov, and V. V. Ershov,Izv. Akad. Nauk SSSR, Ser. Khim., 1978, 1033 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1978,27, 894 (Engl. Transl.)].
M. Attina, F. Cacace, G. Ciarahni, and P. Giacomello,J. Am. Chem. Soc., 1977,99, 5022.
O. S. Chizhov, V. I. Kadentsev, and A. A. Stomakhin,Org. Mass Spectrom., 1991,26, 757.
O. S. Chizhov, V. I. Kadentsev, and A. A. Stomakhin,Org. Mass Spectrom., 1992,27, 699.
W. J. Pietro, S. K. Pollack, and W. J. Henre,J. Am. Chem. Soc., 1979,101, 7126.
R. Walder and J. L. Franklin,Int. J. Mass Spectrom. and Ion Phys., 1980,36, 85.
L. I. Krimen and D. Cota,Org. React., 1969,7, 213.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1767–1773, September, 1995.
This work was carried out with financial support from the International Science Foundation (Grant MA7 000) and the Russian Foundation for Basic Research (Project No. 93-03-18033).
Rights and permissions
About this article
Cite this article
Kadentsev, V.I., Kolotyrkina, N.G., Stomakhin, A.A. et al. Peculiarities of interaction of H+, Me3C+, and Me3Si+ ions with multifunctional molecules in the gas phase. Russ Chem Bull 44, 1698–1704 (1995). https://doi.org/10.1007/BF01151294
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF01151294