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

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.

How to Cite
Ponomarev, O. A.; Surov, Y. N.; Pivnenko, N. S.; Popova, N. A.; Fedyunyaeva, I. A. Chem. Heterocycl. Compd. 1997, 33, 707. [Khim. Geterotsikl. Soedin. 1997, 811.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02291804