Abstract
Formation of a hydrogen bond between molecules of a proton donor (phenol, pyrrole, N-methylanilines) and a solvent decreases the sensitivity of the XH stretching frequency to the polarity/polarizability of solvents. A change in the bond configuration in the amine moiety of N-methylaniline and related compounds upon formation of a solvation H complex is manifested in that the absolute terms of the solvatochromic equations for inert and protophilic media are different. The spectroscopic effect from the geometric reorganization of molecules is determined by their structure and the capability to act as hydrogen bond donors. Multicentered hydrogen bond with π bases affects the geometry of the amine fragment of N-substituted anilines to a lesser extent than does two-centered H bond with onium bases.
Similar content being viewed by others
REFERENCES
Fedorov, S.V., Krivoruchka, I.G., Shulunova, A.M., Sherstyannikova, L.V., Trofimova, O.M., Vokin, A.I., and Turchaninov, V.K., Zh. Obshch. Khim., 2005, vol. 75, no.1, p. 111.
Kamlet, M.J. and Taft, R.W., J. Chem. Soc., Perkin Trans. 2, 1979, no. 3, p. 337.
Kamlet, M.J. and Abboud, J.-L., Abraham, M.H., and Taft, R.W., J. Org. Chem., 1983, vol. 48, no.17, p. 2877.
Schreiber, V.M., J. Mol. Struct., 1989, vol. 197, nos.1–3, p. 73.
Zaitsev, B.E., Fain, V.Ya., Kliot, L.Ya., Sheban, G.V., Bondareva, O.V., and Mikhailova, T.A., Zh. Obshch. Khim., 1988, vol. 58, no.7, p. 1641.
Zaitsev, B.E., Fain, V.Ya., Sheban, G.V., Kliot, L.Ya., and Mikhailova, T.A., Zh. Obshch. Khim., 1991, vol. 61, no.1, p. 206.
Bellamy, L.J. and Hallam, H.E., Trans. Faraday Soc., 1959, vol. 55, no.2, p. 220.
Moritz, A.G., Spectrochim. Acta, 1960, vol. 16, no.4, p. 1176.
Bellamy, L.J., Eglinton, G., and Morman, J.F., J. Chem. Soc., 1961, no. 11, p. 4762.
Osawa, E. and Yoshida, Z., Spectrochim. Acta, Part A, 1967, vol. 23, no.7, p. 2029.
Dyall, L.K. and Kemp, J.E., Spectrochim. Acta, 1966, vol. 22, no.3, p. 483.
Strohbusch, F. and Zimmermann, H., Ber. Bunsenges. Phys. Chem., 1967, vol. 71, no.6, p. 567.
Lautie, A., Laytie, M.F., Gruger, A., and Fakhri, S.A., Spectrochim. Acta, Part A, 1980, vol. 36, no.1, p. 85.
Nozari, M.S. and Drago, R.S., J. Am. Chem. Soc., 1970, vol. 92, no.24, p. 7086.
Abraham, M.H., Grellier, P.L., Abboud, J.-L.M., Doherty, R.M., and Taft, R.W., Can. J. Chem., 1988, vol. 66, no.11, p. 2673.
Dyall, L.K. and Kemp, J.E., Spectrochim. Acta, 1966, vol. 22, no.3, p. 467.
Yokoyama, T., Taft, R.W., and Kamlet, M.J., J. Chem. Soc., Perkin Trans. 2, 1987, no. 7, p. 875.
Gonzalez, G. and Clavijo, E., J. Chem. Soc., Perkin Trans. 2, 1985, no. 11, p. 1751.
Dyall, L.K., Aust. J. Chem., 1967, vol. 20, no.1, p. 93.
Author information
Authors and Affiliations
Additional information
__________
Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 4, 2005, pp. 642–649.
Original Russian Text Copyright © 2005 by Vokin, Oznobikhina, Shulunova, Ustinov, Bozhenkov, Levkovskaya, Turchaninov.
For communication XXV, see [1].
Rights and permissions
About this article
Cite this article
Vokin, A.I., Oznobikhina, L.P., Shulunova, A.M. et al. Solvatochromism of Heteroaromatic Compounds: XXVI. Solvent Effect on the Solvatochromic Parameters of IR Bands of N-Methylanilines and Related Hydrogen Bond Donors. Russ J Gen Chem 75, 605–612 (2005). https://doi.org/10.1007/s11176-005-0280-4
Received:
Issue Date:
DOI: https://doi.org/10.1007/s11176-005-0280-4