Abstract
Intramolecular charge transfer processes in a series of thetrans-isomers of styryl derivatives of pyridines and quinolines, their hydrochlorides and molecular complexes with BF3 have been studied by electronic and IR spectroscopy. Electron donor groups involved in direct resonance conjugation with the N-oxide group intensify these processes, while electron acceptor nitro groups somewhat weaken them. Protons and BF3 coordinate to the oxygen of the N→O group to form strong 1∶1 complexes, except in the cases of 4-(4-dimethylaminostyryl)quinoline and pyridine N-oxides, in which a second acceptor molecule adds to the amino group.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
V. P. Andreev and A. V. Ryzhakov, Khim. Geterotsikl. Soedin., No. 12, 1662 (1993).
V. P. Andreev and A. V. Ryzhakov, Khim. Geterotsikl. Soedin., No. 8, 1087 (1994).
V. P. Andreev, A. V. Ryzhakov, A. K. Morozov, O. O. Alekseeva, and L. L. Rodina, Khim. Geterotsikl. Soedin., No. 6, 760 (1995).
V. P. Andreev, A. V. Ryzhakov, and S. V. Tekanov, Khim. Geterotsikl Soedin., No. 4, 518 (1995).
V. I. Ivanskii, Chemistry of Heterocyclic Compounds [in Russian], Vysshaya Shkola, Moscow (1978), p. 254.
L. I. Bellamy, The Infrared Spectra of Complex Molecules, Vol. 1, Chapman-Hall, London (1975), p. 335.
J. W. Daly and B. Witkop, J. Org. Chem.,27, 4104 (1962).
G. Silverstein, G. Bassler, and T. Morril, Spectroscopic Identification of Organic Compounds [Russian translation], Mir, Moscow (1977), pp. 326, 405, 493, 539.
E. Ochiai, Aromatic Amine Oxides, Elsevier, Amsterdam (1967), pp. 89, 139.
A. R. Katritzky, J. Chem. Soc., No. 6, 2049 (1959).
P. N. Gates and E. F. Mooney, J. Nucl. Chem.,30, 839 (1968).
S. P. Ponomarenko, Yu. A. Borovikov, G. S. Borovikova, T. K. Nikolaenko, and V. P. Makovetskii, Ukr. Khim. Zh.,59, 883 (1993).
A. R. Katritzky, A. J. Boulton, and D. J. Short, J. Chem. Soc., No. 8, 2954 (1960).
A. R. Katritzky, A. J. Boulton, and D. J. Short, J. Chem. Soc. No. 4, 1519 (1960).
A. R. Katritzky, A. J. Boulton, and D. J. Short, J. Chem. Soc., No. 4, 1516 (1960).
V. P. Andreev, E. G. Korvachyova, and I. L. Rodina, 11th International Conference on Organic Synthesis (ICOS-11), Book of Abstracts, Amsterdam (1996). p. 452.
V. P. Andreev, E. G. Kalistratova, and A. V. Ryzhakov, Khim. Geterotsikl. Soedin., No. 4, 516 (1996).
E. D. Parker and A. Furst, J. Org. Chem.,23, 201 (1958).
B. A. Burs and J. H. Bickerton, J. Am. Chem. Soc.,67, 2261 (1945).
Additional information
Petrozavodsk State University, Petrozavodsk 185640, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, 1093–1102, August, 1998.
Rights and permissions
About this article
Cite this article
Andreev, V.P., Batotsyrenova, E.G., Ryzhakov, A.V. et al. Intramolecular charge transfer processes in a series of styryl derivatives of pyridine and quinoline N-oxides. Chem Heterocycl Compd 34, 941–949 (1998). https://doi.org/10.1007/BF02311331
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02311331