Quantum chemical study of the structure and properties of citrinin

被引：8

作者：

Appell, Michael ^{[1
]}

Moravec, David ^{[2
]}

Bosma, Wayne B. ^{[2
]}

机构：

[1] ARS, Bacterial Foodborne Pathogens & Mycol Res Unit, USDA, Natl Ctr Agr Utilizat Res, Peoria, IL 61604 USA

[2] Bradley Univ, Dept Chem & Biochem, Peoria, IL 61625 USA

来源：

MOLECULAR SIMULATION | 2012年 / 38卷 / 04期

关键词：

citrinin; tautomer; density functional theory; thermodynamics; natural bond orbital; DENSITY-FUNCTIONAL THEORY; PROTON-TRANSFER; SOLID-STATE; ACID; ENOLS; OPTIMIZATION; MOLECULES;

D O I：

10.1080/08927022.2011.619984

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：

Detailed structures and electronic properties of three tautomeric forms of the toxin citrinin were investigated using several quantum calculation methods. Energetic preference of the predominant p- and o-quinone methide tautomeric forms is dependent on the method of calculation. A previously unstudied carboxylic acid enol tautomer was calculated to be surprisingly stable in vacuo, being within 2.5 kcal mol(-1) at the B3LYP/6-311++G(2d,2p) level of theory. Despite differences in bond nature and connectivity of tautomers, the natural bond orbital analysis revealed that tautomeric forms share similar natural charges and natural electron configurations. Calculated bond lengths corresponded with experimentally observed values and assignments for the calculated infrared vibrational frequencies are reported.

引用

页码：284 / 292

页数：9

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