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Investigation of Benzimidazoles. 5—transmission of the substituent effects in 2-substituted 5(6)-nitrobenzimidazoles studied by 1H, 13C and 15N NMR spectroscopy

✍ Scribed by V. A. Lopyrev; L. I. Larina; T. I. Vakul'skaya; M. F. Larin; E. F. Shibanova; I. A. Titova; M. G. Voronkov; E. E. Liepin'sh

Publisher
John Wiley and Sons
Year
1985
Tongue
English
Weight
360 KB
Volume
23
Category
Article
ISSN
0749-1581

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✦ Synopsis

The iniluence of substituents on the 'H, "C and 15N NMR chemical shifts of 2-substituted 5(6)nitrobenzimidazoles and their analogues labelled with 15N in the nitro group was investigated. It was found that the substituent effects are transmitted to the carbon and hydrogen nuclei in positions 4-7 mainly by the resonance mechanism, but to the nitro-nitrogen atom with approximately equal contributions from the resonance and inductive components. Comparison of the transmission of substituent effects in nitrobenzimidazoles with para and meta derivatives of nitrobenzene showed that the nitro group seems to be more tightIy conjugated with the benzimidazole fragment than with the benzene ring.

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