Abstract
An authors’ methodology based on the graph theory was used to construct the complete set of group separation reactions (homodesmic reactions, HDRs) for 12 cyclic and bicyclic derivatives of cyclopropane and cyclopropene. The standard absolute enthalpies of all participants of the HDRs were calculated using the composite methods G3 and G4. It was shown that the heat of an HDR is determined by the difference between the strain energy Es of the cyclic compound and the energy of sp3–sp3gauche interactions in the HDR products. The additivity rule was shown to hold for the gauche effect, which made it possible to determine the Es values for the compounds and to trace their dependence on the structural features of C3 cyclic hydrocarbons.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0076–0085, January, 2020.
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Akhmetshina, E.S., Khursan, S.L. Application of group separation reaction formalism for analysis of non-valence effects of organic compounds: three-carbon rings. Russ Chem Bull 69, 76–83 (2020). https://doi.org/10.1007/s11172-020-2725-7
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DOI: https://doi.org/10.1007/s11172-020-2725-7