Premium
Multinuclear NMR and ab initio MO studies of 7‐methyl‐7 H ‐pyrrolo [2,3‐ b ]pyridine and related compounds
Author(s) -
Minakata Satoshi,
Itoh Shinobu,
Komatsu Mitsuo,
Ohshiro Yoshiki,
Yokomichi Yasunori
Publication year - 1993
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610060303
Subject(s) - chemistry , pyridine , ab initio , nuclear magnetic resonance spectroscopy , chemical shift , ab initio quantum chemistry methods , computational chemistry , basis set , crystallography , spectroscopy , stereochemistry , molecule , density functional theory , organic chemistry , physics , quantum mechanics
The contribution of the polarized resonance structures to 7‐methyl‐7 H ‐pyrrolo[2,3,‐ b ]pyridine and 4‐methyl‐4 H ‐pyrrolo [3,2‐ b ] pyridine, which have recently attracted much attention in physico‐chemical studies, was considered based on multinuclear ( 1 H, 13 C and 15 N) NMR spectroscopy and MO calculation. Comparison of the chemical shifts of the compounds with those of other relevant compounds and the effects of concentration and solvents observed by multinuclear NMR suggested that the contribution of the non‐polarized structures to both compounds predominates over that of the polarized structures. This result was also supported by ab initio MO calculations using the 6–31G basis set.