Abstract
The hydrogen-bonded complexes between phenol derivatives and methyl acrylate, methyl trans-crotonate and methyl trans-cinnamate were studied using the interactive molecular modelling program PCMODEL which uses the features of Allinger's MMX force field, including pi-valence electron self-consistent field (Pi-VESCF) calculations. The results successfully reproduce experimental Δ H values associated with the formation of the hydrogen-bonded complexes and account for the experimentally observed dependences of Δ H on the electron releasing/withdrawing abilities of the substituents in the phenol aromatic ring or in the ester. In addition, the conformational change in the ester moiety of the hydrogen-bonded complexes gives rise to energetically similar hydrogen bonds, in agreement with previous infrared spectroscopic results. In general, the results obtained confirm or expand the previous spectroscopic or quantum mechanical results of M. Dulce G. Faria (J. Mol. Struct., 263 (1991) 87; Vib. Spectrosc., 2 (1991) 43, 107), and lead to the possibility of successfully applying the MMX/Pi-VESCF method to the study of hydrogen-bonded complexes involving other biochemically important molecules.
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