Abstract
The hyperconjugative effect of the methyl group in the para and ortho position of the benzene ring is studied as a function of the medium. The ionization and solution enthalpies of ortho and para toluic acids have been measured in H 2O/DMSO mixtures. A study of the ortho effects by means of the linear combination of the ordinary polar, proximity polar and steric effects has also been performed. The methyl group both in ortho and para position seems to be forced out by the benzene ring at X dmso = 0.5 mole fraction with a consequent decrease of hyperconjugation effect. A study of enthalpic and entropic contributions to substituent and reaction constants and the proton transfer process from ortho and para derivatives to benzoic acid, compared with the same process in the gaseous phase are also presented.
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