Skip to main content
SpringerLink
Log in

Molecular Structure of Complexes with Bifurcated Hydrogen Bond: I. N-(4-Methyl-2-nitrophenyl)acetamide

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

According to the results of HF/6-31G* and B3LYP/6-31G* nonempirical calculations, N-(4-methyl- 2-nitrophenyl)acetamide in the synperiplanar and antiperiplanar conformations gives stable complexes with protophilic solvents, which are stabilized by bifurcated (three-center) hydrogen bond. The complexes are characterized by (1) opposite variations of the interatomic distances and angles corresponding to intra- and intermolecular components of the bifurcated hydrogen bond, (2) extension of the intramolecular component and a more pronounced shortening of the intermolecular component with increase in the strength of the three-center H-complex, and (3) nonlinear and nonmonotonic relation between the NH stretching vibration frequency and the energy of complex formation.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. Lutskii, A.E., Prezhdo, V.V., Degtereva, L.I., and Gordienko, V.G., Usp. Khim., 1982, vol. 51, no. 8, pp. 1398-1423.

    Google Scholar 

  2. Bureiko, S.F., Golubev, N.S., Pikhlaya, K., and Mattinen, I., Zh. Strukt. Khim., 1991, vol. 32, no. 1, pp. 87-92.

    Google Scholar 

  3. Albrecht, G. and Corey, R.B., J. Am. Chem. Soc., 1939, vol. 61, no. 5, pp. 1087-1103.

    Google Scholar 

  4. Taylor, R., Kennard, O., and Versichel, W., J. Am. Chem. Soc., 1984, vol. 106, no. 1, pp. 244-248

    Google Scholar 

  5. Jeffrey, G.A. and Maluszynska, H., J. Mol. Struct., 1986, vol. 147, nos. 1–2, pp. 127-142.

    Google Scholar 

  6. Jeffrey, G.A. and Mitra, J., J. Am. Chem. Soc., 1984, vol. 106, no. 19, pp. 5546-5553.

    Google Scholar 

  7. Jeffrey, G.A. and Maluszynska, H., Acta Crystallogr., Sec. B, 1990, vol. 46, no. 4, pp. 546-549.

    Google Scholar 

  8. Dyall, L.K. and Kemp, J.E., Spectrochim. Acta, 1966, vol. 22, no. 3, pp. 467-482.

    Google Scholar 

  9. Magee, M.D. and Walker, S., Can. J. Chem., 1972, vol. 50, no. 17, pp. 2799-2805.

    Google Scholar 

  10. Bureiko, S.F., Oktyabr'skii, V.P., and Pikhlaya, K., Kinet. Katal., 1993, vol. 34, no.3, pp. 430-435.

    Google Scholar 

  11. Bureiko, S.F., Khim. Fiz., 1993, vol. 12, no. 7, pp. 926-933.

    Google Scholar 

  12. Bureiko, S.F. and Oktiabr'sky, V.P., J. Mol. Struct., 1995, vol. 349, nos. 1–3, pp. 53-56.

    Google Scholar 

  13. Bureiko, S.F., Golubev, N.S., and Pihlaja, K., J. Mol. Struct., 1999, vol. 480, nos. 1–3, pp. 297-302

    Google Scholar 

  14. Turchaninov, V.K., Murzina, N.M., Vokin, A.I., Aksamentova, T.N., and Trofimov, B.A., Russ. J. Gen. Chem., 2001, vol. 71, no. 2, pp. 234-242.

    Google Scholar 

  15. Schreiber, V., Koll, A., Kulbida, A., and Majerz, I., J. Mol. Struct., 1995, vol. 348, nos. 1–3, pp. 365-368.

    Google Scholar 

  16. Rozas, I., Alkorta, I., and Elguero, J., J. Phys. Chem. A, 1998, vol. 102, no. 48, pp. 9925-9932.

    Google Scholar 

  17. Goutev, N. and Matsuura, H., J. Phys. Chem. A, 2001, vol. 105, no. 19, pp. 4741-4748.

    Google Scholar 

  18. Forbes, E.J., Morgan, K.J., and Newton, J., J. Chem. Soc., 1963, no. 2, pp. 835-839.

  19. Rae, I.D., Can. J. Chem., 1968, vol. 46, no. 15, pp. 2589-2592.

    Google Scholar 

  20. Moore, J.C., Yeadon, A., and Palmer, R.A., J. Crystallogr. Spectrosc. Res., 1983, vol. 13, no. 4, pp. 279-292.

    Google Scholar 

  21. Fletton, R.A., Lancaster, R.W., Harris, R.K., Kenwright, A.M., Packer, K.J., Waters, D.N., and Yeadon, A., J. Chem. Soc., Perkin Trans. 2, 1986, no. 11, pp. 1705-1709.

  22. Taylor, R. and Kennard, O., Acc. Chem. Res., 1984, vol. 17, no. 9, pp. 320-326.

    Google Scholar 

  23. Bellamy, L.J. and Hallam, H.E., Trans. Faraday Soc., 1959, vol. 55, pp. 220-224.

    Google Scholar 

  24. Richards, J.H. and Walker, S., Trans. Faraday Soc., 1961, vol. 57, no. 3, pp. 406-411.

    Google Scholar 

  25. Dabrowska, U. and Urbanski, T., Spectrochim. Acta, 1965, vol. 21, no. 10, pp. 1765-1771.

    Google Scholar 

  26. Lutskii, A.E. and Degtereva, L.I., Zh. Obshch. Khim., 1979, vol. 49, no. 6, pp. 1369-1375.

    Google Scholar 

  27. Epshtein, L.M., Beloborodov, V.L., Ashkinad-ze, L.D., Golovchenko, L.S., Rokhlina, E.M., Kravtsov, D.N., and Kazitsyna, L.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1979, no. 9, pp. 1963-1968.

  28. Schreiber, V.M., J. Mol. Struct., 1989, vol. 197, pp. 73-85.

    Google Scholar 

  29. Seguin, J.-P., Guillaume-Vilport, F., Uzan, R., and Doucet, J.-P., J. Chem. Soc., Perkin Trans. 2, 1986, no. 6, pp. 773-779.

  30. Simperler, A. and Mikenda, W., Monatsh. Chem., 1997, vol. 128, no. 10, pp. 969-980.

    Google Scholar 

  31. Simperler, A., Lampert, H., and Mikenda, W., J. Mol. Struct., 1998, vol. 448, nos. 2–3, pp. 191-199.

    Google Scholar 

  32. 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 PA: Gaussian, 1998.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    I. G. Krivoruchka, A. I. Vokin & V. K. Turchaninov

Authors
  1. I. G. Krivoruchka
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. I. Vokin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. K. Turchaninov
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Krivoruchka, I.G., Vokin, A.I. & Turchaninov, V.K. Molecular Structure of Complexes with Bifurcated Hydrogen Bond: I. N-(4-Methyl-2-nitrophenyl)acetamide. Russian Journal of Organic Chemistry 38, 1456–1461 (2002). https://doi.org/10.1023/A:1022544102994

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1022544102994

Keywords

Search

Navigation