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Intramolecular interactions in series of oxazole, oxadiazole, and triazole derivatives

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Abstract

A comparison of the PMR spectra of 5-phenyl-2-methyl derivatives of oxazole, 1,3,4-oxadiazole, and 1, 3, 4-triazole with the spectrum of toluene leads to the conclusion that the electron-acceptor character of the heterocycles drops off in the order oxadiazole >oxazole>triazole. The conduction of electronic effects of the substituents by the oxazole ring is at the level of benzene; the 1, 3, 4-oxadiazole ring accomplishes the transmission somewhat better, and the 1,3,4-triazole ring more weakly, than in the case of benzene. The formation of H-complexes with a 1∶1 composition in a system consisting of the azole, phenol, and carbon tetrachloride was investigated by means of IR spectroscopy. The relative n-donor strength, of the heterocycles decreases in the series triazole >oxazole> oxadiazole. The effectiveness of transmission of electronic influence of the substituents in the phenyl radical on the pyridine nitrogen atom, which is the center of complexation, decreases in the series oxazole >oxadiazole>triazole.

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References

  1. S. H. Mareus, W. F. Reynds, and S. T. Miller, J. Org. Chem.,31, No. 6, 1872 (1996).

    Google Scholar 

  2. Yu. A. Zhdanov and V. I. Minkin, Correlation Analysis in Organic Chemistry [in Russian], Izd. Rostov. Univ., Rostov-na-Donu (1966).

    Google Scholar 

  3. A. P. Sadimenko, A. D. Garnovskii, V. N. Sheinker, and O. A. Osipov, Khim. Geterotsikl. Soedin., No. 3, 1299 (1983).

    Google Scholar 

  4. V. A. Chernyshev, V. N. Sheinker, A. D. Garnovskii, and O. A. Osipov, Zh. Obshch. Khim.,47, No. 3, 637 (1977).

    Google Scholar 

  5. V. N. Sheinker, A. D. Garnovskii, V. A. Chernyshev, and O. A. Osipov, Zh. Obshch. Khim.,54, No. 3, 670 (1984).

    Google Scholar 

  6. V. N. Sheinker, A. D. Garnovskii, V. A. Chernyshev, O. A. Osipov, and V. A. Chetverikova, Zh. Obshch. Khim.,54, No. 5, 1176 (1984).

    Google Scholar 

  7. V. N. Sheinker, V. S. Troilina, E. G. Merinova, A. D. Garnovskii, and O. A. Osipov, Zh. Obshch. Khim.,58, No. 1, 194 (1988).

    Google Scholar 

  8. I. P. Gol'dshtein, I. A. Misurkin, N. V. Varentsova, I. E. Palaeva, É. S. Shcherbakova, and E. N. Gur'yanova, Zh. Obshch. Khim.,51, No. 9, 2087 (1981).

    Google Scholar 

  9. L. D. Khamaganova, A. N. Fedotov, I. P. Gol'dshtein, E. S. Domnina, and N. D. Abramova, Zh. Fiz. Khim.,64, No. 2, 575 (1990).

    Google Scholar 

  10. E. N. Gur'yanova, I. P. Gol'dshtein, and I. P. Romm, The Donor-Acceptor Bond [in Russian], Khimiya, Moscow (1973), p. 349.

    Google Scholar 

  11. A. F. Pozharskii, Theoretical Principles of the Chemistry of Heterocycles [in Russian], Khimiya, Moscow (1985).

    Google Scholar 

  12. N. A. Popova, B. M. Krasovitskii, N. S. Pivnenko, and Yu. N. Surov, Khim. Geterotsikl. Soedin., No. 6, 816 (1997).

    Google Scholar 

  13. J. Lange and H. Tondys, Pol. J. Pharmacol. Pharm.,27, No. 1, 203 (1975).

    Google Scholar 

  14. H. A. Having, J. Wildeman, and A. M. van Leusen, Tetrahedron Lett., No. 2, 143 (1976).

    Google Scholar 

  15. Joshikazu Ibata and Ryohi Sato, Chem. Lett., No. 10, 1129 (1978).

    Google Scholar 

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Khar'kov State University, Khar'kov 310077. Institute of Single Crystals, Academy of Sciences of the Ukraine, Khar'kov 310001. Translated from Khimiya Geterotsiklicheskikh, Soedinenii, No. 6, pp. 811–815, June, 1997.

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Ponomarev, O.A., Surov, Y.N., Pivnenko, N.S. et al. Intramolecular interactions in series of oxazole, oxadiazole, and triazole derivatives. Chem Heterocycl Compd 33, 707–711 (1997). https://doi.org/10.1007/BF02291804

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