Destabilization in the isomeric nitrobenzonitriles: an experimental thermochemical study |
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| Institution: | 1. Instituto de Quı́mica Fı́sica “Rocasolano,” CSIC, Serrano 119, 28006 Madrid, Spain;2. Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD 21250, USA;1. Kafkas University, Department of Chemical Engineering, Faculty of Engineering and Architecture, 36300 Kars, Turkey;2. Kafkas University, Department of Electrical and Electronics Engineering, Faculty of Engineering and Architecture, 36300 Kars, Turkey;3. Kafkas University, Department of Chemistry, Faculty of Sciences and Arts, 36300 Kars, Turkey;4. International Scientific Research Centre, Baku State University, 1148 Baku, Azerbaijan;5. Scientific and Technological Application and Research Center, Aksaray University, 68100 Aksaray, Turkey;6. Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey;1. Department of Chemistry, Wayne State University, Detroit, MI 48202, USA;2. Cardiovascular Research Institute, Wayne State University School of Medicine, Detroit, MI 48202, USA;3. Proteomics Core Facility, Institute of Environmental Health Sciences, Wayne State University, Detroit, MI 48202, USA;1. Department of Chemistry, Faculty of Science, The Maharaja Sayajirao University of Baroda, Vadodara 390002, India;2. Department of Zoology, Faculty of Science, The Maharaja Sayajirao University of Baroda, Vadodara 390002, India;1. Key Laboratory of Cloud-Precipitation Physics and Severe Storms (LACS), Institute of Atmospheric Physics, Chinese Academy of Sciences, Beijing, 100029, China;2. University of Chinese Academy of Sciences, Beijing, 100049, China;3. Earth System Science Center, University of Alabama in Huntsville, Huntsville, AL, USA;1. University of the Science, Philadelphia, PA 19104, USA;2. DuPont Corporate Center for Analytical Science, Wilmington, DE 19898, USA |
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| Abstract: | The enthalpies of combustion and of sublimation, respectively, of the three isomeric nitrobenzonitriles have been measured: o-, {(−3456.3±2.9), (88.1±1.4)} kJ·mol−1; m-, {(−3442.8±3.3), (92.8±0.3)} kJ·mol−1; p-, {(−3448.2±3.6), (91.1±1.3)} kJ·mol−1. In turn, from these values, the standard molar enthalpies of formation for the condensed and gaseous state, respectively, have been derived: o-, {(130.1±3.1), (218.2±3.4)} kJ·mol−1; m-, {(116.5±3.5), (209.3±3.5)} kJ·mol−1; p-, {(122.0±3.8), (213.1±4.0)} kJ·mol−1. Destabilization energies associated with the presence of the two electron-withdrawing groups have been determined, for o-, m-, and p-nitrobenzonitrile, {(17.6±4.1), (8.7±4.2), and (12.5±4.6)} kJ·mol−1, respectively, and are consistent with those obtained for the corresponding sets of isomeric methyl benzenedicarboxylates, dicyanobenzenes, dinitrobenzenes, and (neutral and ionized) nitrobenzoic acids. |
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