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Thermochemistry and quantum chemical calculations of two dibenzocycloalkane nitriles

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Abstract

The energies of combustion and fusion of 5-cyano-5H-dibenzo[a,d]cycloheptene (1) and (5E,11E)-dibenzo[a,e]cyclooctene-5,11-dicarbonitrile (2) were measured by means of microbomb calorimetry and DSC, respectively. The derived enthalpies of formation in solid state are 320 ± 18 for nitrile 1 and 470 ± 31 kJ mol−1 for nitrile 2, respectively. The experimental enthalpies of formation are discussed in relationship with values calculated at the G3(MP2)//B3LYP level of quantum chemical theory, by means of group additivity and isodesmic reactions. The two nitriles are not stabilized by dibenzoannelation.

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Authors and Affiliations

  1. Laboratory of General Chemistry, Polytechnic University of Bucharest, str. Polizu 1, Bucharest, Romania

    Ştefan Perişanu

  2. Institute of Physical Chemistry ‘‘I.G. Murgulescu’’ of the Romanian Academy, Bucharest, Romania

    Iulia Contineanu & Ana Neacşu

  3. Instituto de Química Física ‘Rocasolano’, CSIC, Serrano 119, 28006, Madrid, Spain

    Rafael Notario & Maria Victoria Roux

  4. Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, 1000 Hilltop Circle, Baltimore, MD, 21250, USA

    Joel F. Liebman & Bryan J. Dodson

Authors
  1. Ştefan Perişanu
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  2. Iulia Contineanu
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  3. Ana Neacşu
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  4. Rafael Notario
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  5. Maria Victoria Roux
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  6. Joel F. Liebman
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  7. Bryan J. Dodson
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Correspondence to Ştefan Perişanu.

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Perişanu, Ş., Contineanu, I., Neacşu, A. et al. Thermochemistry and quantum chemical calculations of two dibenzocycloalkane nitriles. Struct Chem 22, 89–94 (2011). https://doi.org/10.1007/s11224-010-9691-x

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  • DOI: https://doi.org/10.1007/s11224-010-9691-x

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