Abstract
N-(4-Methyl-2-nitrophenyl)acetamide molecule forms a complex with a protophilic solvent, stabilized by a bifurcate H bond and existing in a labile equilibrium with the nonspecifically solvated molecule. The position of the equilibrium is affected by temperature, phase state, and protophilic properties of the medium. Three-centered solvation H complexes of N-(4-methyl-2-nitrophenyl)acetamide are characterized by nonlinear dependence of the NH stretching frequency on the energy of the complex formation and by the positive specific “dioxane” effect.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Vokin, A.I., Shulunova, A.M., Khil'ko, M.Ya., Lopyrev, V.A., and Turchaninov, V.K., Zh. Obshch. Khim., 2003, vol. 73,no. 7, p. 1206.
Dyall, L.K. and Kemp, J.E., Spectrochim. Acta, 1966, vol. 22,no. 3, p. 467.
Rae, I.D., Can. J. Chem., 1968, vol. 46,no. 15, p. 2589.
Bartels-Keith, J.R. and Cieciuch, R.F.W., Can. J. Chem., 1968, vol. 46,no. 15, p. 2593.
Brown, R.F.C., Radom, L., Sternhell, S., and Rae, I.D., Can. J. Chem., 1968, vol. 46,no. 15, p. 2577.
Lutskii, A.E., Dolzhenko, Yu.I., and Mitichkin, A.I., Zh. Obshch. Khim., 1980, vol. 50,no. 10, p. 2346.
Taylor, R., Kennard, O., and Versichel, W., J. Am. Chem. Soc., 1984, vol. 106,no. 1, p. 244.
Dyall, L.K. and Kemp, J.E., Spectrochim. Acta, 1966, vol. 22,no. 3, p. 483.
Dabrowska, U. and Urbanski, T., Spectrochim. Acta, 1965, vol. 21,no. 10, p. 1765.
Bureiko, S.F., Golubev, N.S., Pihlaja, K., and Mattinen, I., Zh. Strukt. Khim., 1991, vol. 32,no. 1, p. 87.
Wandas, M., Pawelka, Z., and Puszko, A., J. Heterocyclic Chem., 2000, vol. 37,no. 2, p. 335.
Turchaninov, V.K., Murzina, N.M., Vokin, A.I., Aksamentova, T.N., and Trofimov, B.A., Zh. Obshch. Khim., 2001, vol. 71,no. 2, p. 261.
Skvortsov, I.M., Fedorov, E.E., and Mushtakova, S.P., Zh. Fiz. Khim., 1986, vol. 60,no. 8, p. 2065.
Khafizov, F.T., Breus, V.A., Kiselev, O.E., Solomonov, B.N., and Konovalov, A.I., Zh. Obshch. Khim., 1990, vol. 60,no. 4, p. 721.
Kamlet, M.J., Abboud, J.-L., Abraham, M.H., and Taft, R.W., J. Org. Chem., 1983, vol. 48,no. 17, p. 2877.
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.
Schreiber, V.M., J. Mol. Struct., 1989, vol. 197,nos. 1–;3, p. 73.
Yokoyama, T., Taft, R.W., and Kamlet, M.J., J. Chem. Soc., Perkin Trans. 2, 1987, no. 7, p. 875.
Minkin, V.I., Osipov, O.A., and Zhdanov, Yu.A., Dipol'nye momenty v organicheskoi khimii (Dipole Moments in Organic Chemistry), Leningrad: Khimiya, 1968.
Exner, O., Koudelka, J., and Vasickova, S., Coll. Czech. Chem. Commun., 1983, vol. 48,no. 3, p. 735.
Osipov, O.A., Minkin, V.I., and Garnovskii, A.D., Spravochnik po dipol'nym momentam (Handbook on Dipole Moments), Moscow: Vysshaya Shkola, 1971.
Smith, J.W. and Walshaw, S.M., J. Chem. Soc., 1959, no. 12, p. 3784.
Lutskii, A.E. and Kondratenko, B.P., Zh. Fiz. Khim., 1959, vol. 33,no. 9, p. 2017.
Turchaninov, V.K., Vokin, A.I., Aksamentova, T.N., Krivoruchka, I.G., Shulunova, A.M., and Andriyankova, L.V., Zh. Obshch. Khim., 2003, vol. 73,no. 5, p. 786.
Vokin, A.I., Sherstyannikova, L.V., Krivoruchka, I.G., Aksamentova, T.N., Krylova, O.V., and Turchaninov, V.K., Zh. Obshch. Khim., 2003, vol. 73,no. 6, p. 1028.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery, J.A., Stratmann, R.E., Burant, J.C., Dapprich, S., Millam, J.M., Daniels, A.D., Kudin, K.N., Strain, M.C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G.A., Ayala, P.Y., Cui, Q., Morokuma, K., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortiz, J.V., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Gonzalez, C., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Andres, J.L., Gonzalez, C., Head-Gordon, M., Replogle, E.S., and Pople, J.A., GAUSSIAN 98, Rev. A.6, Pittsburgh: Gaussian, 1998.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Krivoruchka, I.G., Vokin, A.I., Aksamentova, T.N. et al. Solvatochromism of Heteroaromatic Compounds: XXII. Effect of Bifurcate Hydrogen Bond on the IR Spectrum and Dipole Moment of N-(4-Methyl-2-nitrophenyl)acetamide in Solution. Russian Journal of General Chemistry 74, 120–127 (2004). https://doi.org/10.1023/B:RUGC.0000025179.71808.49
Issue Date:
DOI: https://doi.org/10.1023/B:RUGC.0000025179.71808.49