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Issue 33, 2013
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Modeling the mechanism of glycosylation reactions between ethanol, 1,2-ethanediol and methoxymethanol

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Abstract

The mechanism of the SN2 model glycosylation reaction between ethanol, 1,2-ethanediol and methoxymethanol has been studied theoretically at the B3LYP/6-311+G(d,p) computational level. Three different types of reactions have been explored: (i) the exchange of hydroxyl groups between these model systems; (ii) the basic catalysis reactions by combination of the substrates as glycosyl donors (neutral species) and acceptors (enolate species); and (iii) the effect on the reaction profile of an explicit H2O molecule in the reactions considered in (ii). The reaction force, the electronic chemical potential and the reaction electronic flux have been characterized for the reaction path in each case. Energy calculations show that methoxymethanol is the worst glycosyl donor model among the ones studied here, while 1,2-ethanediol is the best, having the lowest activation barrier of 74.7 kJ mol−1 for the reaction between this one and the ethanolate as the glycosyl acceptor model. In general, the presence of direct interactions between the atoms involved in the penta-coordinated TS increases the activation energies of the processes.

Graphical abstract: Modeling the mechanism of glycosylation reactions between ethanol, 1,2-ethanediol and methoxymethanol

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Publication details

The article was received on 09 May 2013, accepted on 24 Jun 2013 and first published on 25 Jun 2013


Article type: Paper
DOI: 10.1039/C3CP51963E
Citation: Phys. Chem. Chem. Phys., 2013,15, 14026-14036
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    Modeling the mechanism of glycosylation reactions between ethanol, 1,2-ethanediol and methoxymethanol

    L. M. Azofra, I. Alkorta, A. Toro-Labbé and J. Elguero, Phys. Chem. Chem. Phys., 2013, 15, 14026
    DOI: 10.1039/C3CP51963E

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