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A theoretical study on C–H bond dissociation enthalpies of oxygen-containing fused heterocyclic compounds

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Abstract

The C–H bond dissociation enthalpies (BDEs) of 27 N, O, S-containing mono-heterocyclic compounds were assessed by the composite high-level ab initio methods G4 and G3B3. After comparing the theoretical C–H BDEs of 32 N, O, S-containing heterocyclic compounds by using 10 density functional theory methods with experimental ones, we found that the BMK method provided the lowest root of mean square error of 7.2 kJ/mol. Subsequently, we calculated the C–H BDEs of oxygen-containing fused heterocyclic compounds at different positions by the BMK method. The results indicated that there are large BDE differences between the C(sp 3)–H bonds. In order to find the essence of the C–H BDE differences, NBO and molecular orbital analyses were conducted. In addition, the substituent effects on C–H BDEs in oxygen-containing fused heterocyclic compounds were discussed. Finally, we found two linear relationships between the BDEs and qO/e in the oxygen-containing fused heterocyclic compounds for different substituents, and the corresponding correlation coefficient squares (R 2) were 0.8551 and 0.9379, respectively.

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Acknowledgments

This study was financed by the graduate research and innovation fundings (13KY0402, 14KY0403). We also thank Shanghai Supercomputer Center for the computational resources.

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  1. Department of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, 201620, China

    Ying Xing Wang & Wen Rui Zheng

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  1. Ying Xing Wang
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Correspondence to Wen Rui Zheng.

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Wang, Y.X., Zheng, W.R. A theoretical study on C–H bond dissociation enthalpies of oxygen-containing fused heterocyclic compounds. Res Chem Intermed 41, 7207–7225 (2015). https://doi.org/10.1007/s11164-014-1807-2

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