Quantum chemical studies of azoles 2. Thermodynamic stability of neutral molecules and intermediates formed during electrophilic substitution of 1,2- and 1,3-azoles

被引：0
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作者：
L. I. Belen´kii
I. D. Nesterov
N. D. Chuvylkin
机构：
[1] Russian Academy of Sciences,N. D. Zelinsky Institute of Organic Chemistry
来源：
Russian Chemical Bulletin | 2014年 / 63卷
关键词：
1,2-azoles; 1,3-azoles; electrophilic substitution; quantum chemical calculations; DFT/B3LYP/6-31G(D) method;
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摘要：
The thermodynamic stability of 1,2- and 1,3-azole molecules, as well as of cationic and bipolar (carbenoid) intermediates in the gas phase and in aqueous solution formed by electrophilic substitution (proton as a model electrophile) was compared based on the analysis of quantum chemical calculations performed at the DFT/B3LYP/6-31G(D) level of theory with zero-point energy corrections. The differences in the chemical behavior of the isomeric 1,2- and 1,3-azole pairs, viz., pyrazole—imidazole, isoxazole—oxazole, and isothiazole—thiazole, were considered.
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页码：2236 / 2242
页数：6
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