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Matos, M. A. R.; Miranda, M. S.; Morais, V. M. F.; Liebman, J. F., Eur. J. Org. Chem. 2004, 3340. Direct calorimetric and phase change enthalpy measurements resulted in an enthalpy of formation of gaseous anthranil of 180.8 ± 2.1 kJ/mol while a combined analysis from reaction calorimetry and quantum chemical calculations resulted in an enthalpy of formation of benz[d]isoxazole of 138.9 ± 4.3 kJ/mol. Direct combustion calorimetry could not be applied to this latter species because of its instability and reluctant lack of sample purity.
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Hussein, A.; Akasheh, T. S., Dirasat-Univ. Jordan; 1985, 12, 65. More precisely, we have the enthalpy of formation of its diphenyl derivative, 203 ± 10 kJ/mol. From equating the difference of the diphenyl and parent heterocycles with that of p-terphenyl and benzene results in the quoted 7 ± 13 kJ/mol. Balepin, A. A.; Lebedev, V. P.; Miroshnichenko, E. A.; Koldobskii, G. I.; Ostovskii, V. A.; Larionov, B. P.; Gidaspov, B. P.; Lebedev, Yu. A., Svoistva Veshchestv. Str. Mol. 1977, 93. The value for terphenyl is 279 ± 6.3 kJ/mol. The archival value for benzene is 82.6 ± 0.7 kJ/mol. Much the same is found using the generally applicable dephenylation enthalpy of ca. 97 kJ/mol suggested in Slayden, S. W., Liebman, J. F., Chem Rev.; 2001, 101, 541.
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Hussein, A.; Akasheh, T. S., Dirasat-Univ. Jordan; 1985, 12, 65. More precisely, we have the enthalpy of formation of its diphenyl derivative, 203 ± 10 kJ/mol. From equating the difference of the diphenyl and parent heterocycles with that of p-terphenyl and benzene results in the quoted 7 ± 13 kJ/mol. Balepin, A. A.; Lebedev, V. P.; Miroshnichenko, E. A.; Koldobskii, G. I.; Ostovskii, V. A.; Larionov, B. P.; Gidaspov, B. P.; Lebedev, Yu. A., Svoistva Veshchestv. Str. Mol. 1977, 93. The value for terphenyl is 279 ± 6.3 kJ/mol. The archival value for benzene is 82.6 ± 0.7 kJ/mol. Much the same is found using the generally applicable dephenylation enthalpy of ca. 97 kJ/mol suggested in Slayden, S. W., Liebman, J. F., Chem Rev.; 2001, 101, 541.
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We have been perhaps too generous. The value suggested p-difluorobenzene in ref. 71 and the contemporary, archival one differ by 100's of kJ/mol!
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