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13C, 14N, 15N and 17O NMR spectra of nitropyrroles and nitroimidazoles

✍ Scribed by E. Lippmaa; M. Mägi; S. S. Novikov; L. I. Khmelnitski; A. S. Prihodko; O. V. Lebedev; L. V. Epishina

Publisher
John Wiley and Sons
Year
1972
Tongue
English
Weight
459 KB
Volume
4
Category
Article
ISSN
0749-1581

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✦ Synopsis

Carbon, nitrogen and oxygen NMR spectra of some nitro derivatives of pyrrole and imidazole have been investigated. The 13C chemical shifts of para-carbons and the 170 chemical shifts of the nitro group correlate qualitatively with the electron densities on these carbon and oxygen atoms, which in turn depend upon the degree of conjugation of the nitro groups with the heterocyclic ring. Conjugation of several nitro groups with the benzene ring is in most cases not impaired by mutual interactions and the 13C shifts show good additivity. Such additivity is much worse in pyrrole and imidazole derivatives. Taken together with the diamagnetic nature of these deviations from additivity, this leads to a possible conclusion about the less pronounced conjugation of the nitro groups with the heterocyclic ring in heterocyclic dinitro derivatives.

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