A DFT study on the chiral synthesis of R-phenylacetyl carbinol within the quantum chemical cluster approach

被引：5

作者：

Alvarado, Omar ^{[1
]}

Lizana, Ignacio ^{[1
]}

Jana, Gonzalo ^{[2
]}

Tunon, Inaki ^{[3
]}

Delgado, Eduardo ^{[1
]}

机构：

[1] Univ Concepcion, Dept Fis Quim, Fac Ciencias Quim, Concepcion, Chile

[2] Univ Andres Bello, Fac Ciencias Exactas, Sede Concepcion, Dept Ciencias Quim, Santiago, Chile

[3] Univ Valencia, Dept Quim Fis, E-46100 Burjassot, Spain

来源：

CHEMICAL PHYSICS LETTERS | 2017年 / 677卷

关键词：

ALPHA-HYDROXY KETONES; ACETOHYDROXYACID SYNTHASE; CARBOLIGATION REACTION; ESCHERICHIA-COLI; ENZYME; INTERMEDIATE; SUBSTRATE; CATALYSIS;

D O I：

10.1016/j.cplett.2017.03.066

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The reaction pathway leading to R-phenylacetyl carbinol within the quantum chemical cluster approach is addressed by means of density functional theory (DFT) calculations. The study includes calculation of Fukui functions, activation free energies, and potential energy surface scans, both in gas and solution phase. The protonation states of the nitrogen atoms of the pyrimidine moiety are determined. The reaction appears to be slightly exergonic (Delta G(0) = -5.6 and -4.0 kcal/mol for gas and solution phase, respectively) following a concerted synchronous mechanism having activation free energy barriers of 16.2 and 13.3 kcal/mol, in gas phase and solution phase, respectively. (C) 2017 Published by Elsevier B.V.

引用

页码：30 / 34

页数：5

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