Abstract
The vicinal effect on chlorination reactions of diols was investigated by computational methods. Applying density functional theory (DFT) combined with polarizable continuum model (PCM) and explicit solvent molecules, we demonstrated the effect of hydration on the leaving and vicinal hydroxyl group in SN2 reactions of selected alcohols. Our results point out to the importance of intermolecular hydrogen bonds as a stabilizing factor in reaction pre-complexes and alcohols with vicinal hydroxyl groups, highlighting the importance of solute-solvent network formation. This indicates the significance of adequately describing the solvent in the study of reaction mechanisms, in special when the interaction with solute molecules and ions are strong. Also, we found a “vinical effect” on the reactivity, in other words, alcohols with vicinal hydroxyl groups exhibit higher activation energies when compared to related monoalcohols. Moreover, 1,3-propanediol and 1,3-butanediol present the highest activation energies.
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