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Determination of aromaticity indices of thiophene and furan by nuclear magnetic resonance spectroscopic analysis of their phenyl esters
Author(s) -
Lee Chang Kiu,
Yu Ji Sook,
Lee HyeJin
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390615
Subject(s) - chemistry , furan , benzoates , aromaticity , thiophene , chloroform , chemical shift , sulfoxide , organic chemistry , medicinal chemistry , molecule
A series of m ‐ and p ‐substituted phenyl benzoates, 2‐thienoates, and 2‐furoates were prepared and their 1 H and 13 C nmr spectroscopic characteristics were examined. In general, good correlations were observed between the chemical shift values of protons and carbons of the acyl aromatic rings and the Hammett σ. Plots of the chemical shift values of the carbonyl carbons of the benzoates against those of the 2‐thienoates and 2‐furoates gave an excellent correlation and the values of the slopes are 0.85 and 0.75, respectively, in dimethyl sulfoxide‐ d 6 and 0.90 and 0.78, respectively, in chloroform‐ d . The values could be considered as a set of aromaticity indices.