Determination of aromaticity indices of thiophene and furan by nuclear magnetic resonance spectroscopic analysis of their phenyl esters

A series of m- and p-substituted-phenyl benzoates, 2-thienoates, and 2-furoates were prepared and their H-1 and C-13 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 sigma. 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.