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Aspects of the Aromaticity of Anthranil
Author(s) -
Matos M. Agostinha R.,
Miranda Margarida S.,
Morais Victor M. F.,
Liebman Joel F.
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400158
Subject(s) - chemistry , isothermal microcalorimetry , aromaticity , standard enthalpy of formation , enthalpy , isodesmic reaction , enthalpy of fusion , calorimetry , thermochemistry , enthalpy of atomization , enthalpy of vaporization , sublimation (psychology) , organic chemistry , computational chemistry , thermodynamics , standard enthalpy change of formation , melting point , molecule , psychology , psychotherapist , physics
The standard ( p ° = 0.1 MPa) molar enthalpy of formation of liquid anthranil was measured at T = 298.15 K by static bomb calorimetry and the standard molar enthalpy of vaporization at T = 298.15 K was obtained using Calvet microcalorimetry. These values were used to derive the standard molar enthalpy of formation of anthranil in the gaseous phase. Thermochemical and quantum chemical comparisons were made to interrelate anthranil and its isomers, 1,2‐benzisoxazole, benzoxazole and 2‐cyanophenol, and the monocyclic heterocycles, isoxazole and oxazole. Comparisons with benzofurazan and isobenzofuran were also made. Additionally nucleus‐independent chemical shifts were used as an aromaticity index. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)