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Constructing a Complete Set of Homodesmic Reactions Using the Depth-First Search Procedure

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Abstract

A graph-theoretical algorithm based on the depth-first search (DFS) procedure of graph analysis is proposed for determining a complete set of homodesmic reactions (HDRs) of organic compounds. The complete set of HDRs is constructed decomposing the molecular graph of a compound into a series of simpler components. Based on the resulting DFS algorithm, a program for plotting the HDR basis is devised that includes automated generation of the structures of homodesmic reaction participants and primary thermochemical analysis (i.e., calculating the heat effects of HDRs from absolute enthalpies of reactants obtained via user-selected quantum chemistry). The work of the algorithm is illustrated by the example of vinylcyclopropane. The use of complete sets of HDRs for the thermochemical analysis of molecular energetics is studied to determine its advantages: high precision; the possibility of controlling the reproducibility of data and screening out inconsistent or erroneous thermochemical data; quantitative consideration of the nonvalence structural effects in organic compounds; and block analysis of the thermochemistry of structurally similar organic compounds, which is analogous to the familiar concept of active thermochemical tables.

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ACKNOWLEDGMENTS

All quantum chemical calculations were made using equipment at the Chemistry shared resource center of the Ufa Institute of Chemistry and the Agidel regional shared resource center of the Ufa Federal Research Center.

Funding

This work was performed as part of a State Task for the Ufa Institute of Chemistry, topic no. AAAA-A20-120012090030-6. It was supported by the Russian Foundation for Basic Research, project no. 18-07-00584 A.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    S. L. Khursan

  2. Bashkir State University, 450076, Ufa, Russia

    A. S. Ismagilova & A. I. Akhmet’yanova

  3. Ufa State Petroleum Technological University, 450000, Ufa, Russia

    F. T. Ziganshina

Authors
  1. S. L. Khursan
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  2. A. S. Ismagilova
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  3. F. T. Ziganshina
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  4. A. I. Akhmet’yanova
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Corresponding authors

Correspondence to S. L. Khursan, A. S. Ismagilova, F. T. Ziganshina or A. I. Akhmet’yanova.

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Translated by K. Utegnov

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Khursan, S.L., Ismagilova, A.S., Ziganshina, F.T. et al. Constructing a Complete Set of Homodesmic Reactions Using the Depth-First Search Procedure. Russ. J. Phys. Chem. 95, 1386–1393 (2021). https://doi.org/10.1134/S0036024421070141

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  • DOI: https://doi.org/10.1134/S0036024421070141

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