Author:
Blackburn Barry J.,Ankrom Douglas W.,Hutton Harold M.
Abstract
Carbon-13 nmr chemical shift assignments are reported for a series of 5-substituted benzimidazoles, 2-methylbenzimidazole, and 5,6-dimethylbenzimidazole. By employing the three-parameter equation of Smith and Proulx, the chemical shifts of all the ring carbons of the 5-substituted compounds are correlated with F and R of Swain and Lupton and Q of Schaefer; only the ipso carbon, C-5, has chemical shifts with a correlation coefficient less than 0.953. These correlations are compared with those obtained from the Swain–Lupton and Taft relationships; in general those from the latter two approaches are found to be less satisfactory. Correlations of the same chemical shifts with excess charge density values, calculated at the INDO level of approximation, are also presented.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
15 articles.
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