Abstract
It was shown on the basis of X-ray structural and NMR data that the (sp 2→sp 3) rehybridization of the oxygen atom of the N→O group can take place in reactions of heteroaromatic N-oxides with Lewis and Bronsted-Lowry acids. The hybridization type depends on the ligand and acceptor natures, composition of a complex, and spatial stresses arising during the complex formation.
Similar content being viewed by others
References
Karayannis, N.M., Pytlewski, L.L., and Mikulski, C.M., Coord. Chem. Rev., 1973, vol. 11, p. 93.
Albini, A. and Pietra, S., Heterocyclic N-Oxides, Raton B. and Arbor A., Eds., Boston: CRC Press, 1991.
Litvinenko, L.M. and Oleinik, N.M., Mekhaniazmy deistviya organicheskikh katalizatorov. Osnovnyi i nukleofil’nyi kataliz (Mechanism of the Operation of Organic Catalysts. Basic and Nucleophilic Catalysis), Kiev: Naukova Dumka, 1984.
Savelova, V.A., Popov, A.F., Solomoichenko, T.N., Sadovskii, Yu.A., Piskunova, Zh.P., and Lobanova, O.V., Zh. Org. Khim., 2000, vol. 36, no. 10, p. 1502.
Rybachenko, V.I., Chotii, K.Yu., Kovalenko, V.V., and Schroder, G., Zh. Obshch. Khim., 2001, vol. 71, no. 5, p. 839.
Schroder, G., Rybachenko, V.I., Chotii, K.Yu., Kovalenko, V.V., Grebenyuk, L.V., Lenska, B., and Eitner, K., Zh. Obshch. Khim., 2003, vol. 73, no. 3, p. 486.
Andreev, V.P. and Nizhnik, Ya.P., Koord. Khim., 2007, vol. 33, no. 9, p. 703.
Kliegel, W., Schumacher, U., Rettig, S.J., and Trotter, J., Can. J. Chem., 1991, vol. 69, p. 1212.
Sorensen, G.O., Tang-Pedersen, A., and Pedersen, E.J., J. Mol. Struct., 1983, vol. 101, nos. 3–4, p. 263.
Rybakov, V.B., Semenova, T.A., Aleshina, L.A., Andreev, V.P., Nizhnik, Y.P., and Chernyshev, V.V., Acta Cryst., E, 2004, vol. 60, p. 901.
Ivashevskaja, S.N., Aleshina, L.A., Andreev, V.P., Nizhnik, Y.P., Chernyshev, V.V., and Schenk, H., Acta Cryst., C, 2002, vol. 58, p. 300.
Ivashevskaja, S.N., Aleshina, L.A., Andreev, V.P., Nizhnik, Y.P., and Chernyshev, V.V., Acta Cryst., E, 2002, vol. 58, p. 721.
Ivashevskaja, S.N., Aleshina, L.A., Andreev, V.P., Nizhnik, Y.P., and Chernyshev, V.V., Acta Cryst., E, 2002, vol. 58, p. 920.
Andreev, V.P. and Ryzhakov, A.V., Khim. Geterotsikl. Soed., 1994, no. 8, p. 1087.
Andreev, V.P., Batotsyrenova, E.G., Ryzhakov, A.V., and Rodina, L.L., Khim. Geterotsikl. Soed., 1998, no. 8, p. 1093.
Andreev, V.P., Nizhnik, Ya.P., Tunina, S.G., and Belashev, B.Z., Khim. Geterotsikl. Soed., 2002, no. 5, p. 634.
Allen, F.H., Acta Cryst., B, 2002, vol. 58, p. 380.
Farrugia, L.J., J. Appl. Cryst., 1997, vol. 30, p. 565.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © V.P. Andreev, V.V. Vapirov, Ya.P. Nizhnik, L.A. Aleshina, T.A. Semenova, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 5, pp. 830–840.
Rights and permissions
About this article
Cite this article
Andreev, V.P., Vapirov, V.V., Nizhnik, Y.P. et al. Change in the hybridization of the N→O group oxygen atom upon complex formation of pyridine and quinoline N-oxides with v-acceptors. Russ J Gen Chem 78, 973–983 (2008). https://doi.org/10.1134/S1070363208050241
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363208050241