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NMR studies on the restricted rotation of 1‐[2‐(1‐phenyl) propyl]‐2,5‐dimethylpyrrole derivatives
Author(s) -
Kashima Choji,
Maruyama Tatsuya,
Fujioka Yoko,
Harada Kazuo
Publication year - 1988
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.610010402
Subject(s) - chemistry , conformational isomerism , substituent , pyrrole , nitrogen atom , group (periodic table) , carbon 13 nmr , proton nmr , stereochemistry , computational chemistry , rotation (mathematics) , carbon atom , medicinal chemistry , ring (chemistry) , organic chemistry , molecule , geometry , mathematics
From the 1 H‐NMR spectra of the various pyrrole compounds, 1‐substituted 2,5‐dimethylpyrroles having two substituent groups on the carbon adjacent to the nitrogen atom were found to be very much hindered compounds. 1‐[(1‐Substituted)‐2‐phenylethyl]‐2,5‐dimethylpyrroles showed the restricted rotation, and the phenyl group of the most stable conformer was in close proximity to the pyrrole group due to dipole interaction. These NMR observations were supported by force field conformational analysis.