A quantum chemical approach to the water assisted neutral hydrolysis of ethyl acetate and its derivatives
1999; Royal Society of Chemistry; Volume: 1; Issue: 6 Linguagem: Inglês
10.1039/a808558g
ISSN1463-9084
Autores Tópico(s)Free Radicals and Antioxidants
ResumoA quantum chemical approach to the neutral water assisted hydrolysis of ethyl acetate and its halogenated derivatives in the gas phase is presented. Calculations of a cluster containing one ester and two water molecules were accomplished with the progam Gaussian 94 at the semi-empirical AM1 and the abinitio RHF/3-21G and RHF/6-31+G(d) computational levels. For each method the Gibbs energies of several key structures along the reaction path were calculated after full geometry optimization. For the proposed first reaction step a transition state with tetrahedral structure at the carbonyl carbon of the ester was found, thus corroborating experimental studies. The computed Gibbs energy of activation of the first reaction reveals a similar influence of polar substituents on this reaction as found by experiments in the liquid phase.
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