Thermochemical study of the isomeric compounds: 3-acetylbenzonitrile and benzoylacetonitrile |
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| Institution: | 1. Centro de Investigação em Química, Department of Chemistry and Biochemistry, Faculty of Science, University of Porto, Rua do Campo Alegre, 687, P-4169-007 Porto, Portugal;2. Instituto de Ciências Biomédicas Abel Salazar, ICBAS, University of Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal;1. Department of Chemistry, Ankara University, 06100 Tandogan, Ankara, Turkey;2. Department of Chemistry, Anadolu University, 26470 Yeniba?lar, Eski?ehir, Turkey;3. Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey;1. Far Eastern Federal University, Vladivostok, Russia;2. Institute of Chemistry, Far-Eastern Branch, Russian Academy of Sciences, Vladivostok, Russia;1. Far Eastern Federal University, Vladivostok, Russia;2. Institute of Chemistry FEBRAS, Vladivostok, Russia;1. LATA2M, Laboratoire de Thermodynamique Appliquée et Modélisation Moléculaire, University of Tlemcen, Post Office Box 119, Tlemcen 13000, Algeria;2. Laboratoire Multimatériaux et Interfaces, UMR 5615, Université de Lyon, Université Claude Bernard Lyon1, 69622 Villeurbanne, France;3. Université de Saint Etienne, Jean Monnet, F-42023 Saint Etienne – Université de Lyon, F-42023 Saint Etienne, France |
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| Abstract: | The standard (p° = 0.1 MPa) molar enthalpies of formation of 3-acetylbenzonitrile and benzoylacetonitrile, in the crystalline phase, were derived from the respective standard massic energies of combustion measured by static bomb combustion calorimetry, in oxygen, at T = 298.15 K. The standard molar enthalpies of sublimation, at T = 298.15 K, were measured by Calvet microcalorimetry. From the above experimentally determined enthalpic parameters, the standard molar enthalpies of formation in the gaseous phase, at T = 298.15 K, are found to be: (52.4 ± 2.1) kJ · mol?1 and (74.8 ± 2.5) kJ · mol?1 for 3-acetylbenzonitrile and benzoylacetonitrile, respectively.Molecular structures were computed using highly accurate ab initio techniques. Standard molar enthalpies of formation of the experimentally studied compounds were derived using an appropriate set of working reactions. Very good agreement between the calculated and the experimental values was obtained, so the calculations were extended to the estimates of the standard molar enthalpies of formation of 2- and 4-acetylbenzonitriles whose study was not performed experimentally.Our results were further interpreted and rationalized in terms of the enthalpic stability and compared to other relevant disubstituted benzenes. |
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| Keywords: | Energy of combustion Enthalpy of formation Enthalpy of sublimation Theoretical calculations 3-Acetylbenzonitrile Benzoylacetonitrile |
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