Effect of Substituents on the Interaction of some Phenols and Thiophenols with Ketones and Nitrobenzene through Ultrasonic Velocity Measurements

Abstract

Effect of substituents on the intermolecular interactions of
phenols with ketones or nitrobenzene has been studied through
ultrasonic velocity measurements.  0- and p-Ch!nrophenols show
stronger interaction than phenols which is in agreement with the
fact that they are more acidic than phenols. However, m-isomer
shows abnormal behaviour. In the case of cresols and 2.6-dimethylphenol,
the interaction is weak when compared to phenol. Here too,
the m-cresol does not fall in line with  o- and p-isomers. This study
is extended to substituted thiophenols also in place of phenols. A
similar trend is seen in the case of chlorothiophenols as found in
the case of chlorophenols. In thiocresols. the interaction is so weak
that the differences in the strength of interaction among 0-,  m- and
p-isomers do not merit discussion. An explanation based on structural
arrangements is offered for the deviation shown by the
m-isomer from the acidity trend in the strength of interaction.