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

A theoretical study on C–H bond dissociation enthalpies of oxygen-containing fused heterocyclic... 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

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

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Publisher
Springer Netherlands
Copyright
Copyright © 2014 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-014-1807-2
Publisher site
See Article on Publisher Site

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.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Sep 20, 2014

References

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