Autor: |
Trofimov, B. A., Golovanova, N. I., Mikhaleva, A. I., Korostova, S. E., Vasil'ev, A. N., Balabanova, L. N. |
Zdroj: |
Chemistry of Heterocyclic Compounds; July 1977, Vol. 13 Issue: 7 p739-742, 4p |
Abstrakt: |
The relative basicities of a series of N-vinylpyrroles and some of their analogs with saturated substituents attached to the nitrogen atom were investigated (the ?vOH shifts in the IR spectrum of phenol were measured). The vOH values were measured in the interval 100–150 cm-1. Alkyl substituents in the 2 and 3 positions raise the basicity of the pyrrole ring, while a phenyl substituent in the 2 position lowers it. N-Vinyl-pyrroles are ~25% less basic than their limiting analogs-N-ethyl- and N-(2'-alkylthioethyl)pyrroles. The inductive effect of the substituent makes the major contribution to the basicities of the investigated pyrroles. The ?vOH values for N-vinyl-2,3-diphenylpyrrole are not in conformity with the general tendencies and constitute evidence for the appreciable contribution of continuous conjugation through the double bond, the pyrrole ring, and the benzene ring in the 3 position. |
Databáze: |
Supplemental Index |
Externí odkaz: |
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