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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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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DOI: https://doi.org/10.1007/BF02291804