Nearest-Neighbor and Non-Nearest-Neighbor Interactions between Substituents in the Benzene Ring. Experimental and Theoretical Study of Functionally Substituted Benzamides

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• 作者：Sergey P. VerevkinVladimir N. Emel’yanenko ; Ruslan N. Nagrimanov
• 刊名：Journal of Physical Chemistry A
• 出版年：2016
• 出版时间：December 15, 2016
• 年：2016
• 卷：120
• 期：49
• 页码：9867-9877
• 全文大小：451K
• ISSN：1520-5215

文摘

Standard molar enthalpies of formation of 2- and 4-hydroxybenzamides were measured by combustion calorimetry. Vapor pressures of benzamide and 2-hydroxybenzamide were derived by the transpiration method. Standard molar enthalpies of sublimation or vaporization of these compounds at 298 K were obtained from vapor pressure temperature dependence. Thermochemical data on benzamides with hydroxyl, methyl, methoxy, amino, and amide substituents were collected, evaluated, and tested for internal consistency. The high-level G4 quantum-chemical method was used for mutual validation of the experimental and theoretical gas-phase enthalpies of formation. Sets of nearest-neighbor and non-nearest-neighbor interactions between substituents in the benzene ring have been evaluated. A simple incremental procedure has been suggested for a quick appraisal of the vaporization and gas-phase formation enthalpies of the substituted benzamides.