CONFORMATIONAL FEATURES OF MONOCHLORO-SUBSTITUTED TETRAHYDROPYRANS ACCORDING TO DATA FROM <i>ab initio</i> CALCULATIONS AND <sup>35</sup> Cl NQR

Authors

  • В. П. Фешин Institute of Technical Chemistry, Urals Branch of the Russian Academy of Sciences, Perm
  • Л. И. Жижина Institute of Technical Chemistry, Urals Branch of the Russian Academy of Sciences, Perm
  • Е. В. Фешина Institute of Technical Chemistry, Urals Branch of the Russian Academy of Sciences, Perm

DOI:

https://doi.org/10.1007/8366

Keywords:

chlorine-substituted tetrahydropyrans, axial and equatorial bonds, conformational energy, RHF/6-31G(d) and MP2/6-31G(d) calculations

Abstract

Nonempirical quantum-chemical calculations of 2-, 3-, and 4-chloro-substituted tetrahydropyrans by the RHF/6-31G(d) and MP2/6-31G(d) methods showed that their conformational energy increases in the transition from the 4- to the 3-chloro-substituted compound, while in the transition to the 2-substituted compound the sign changes. In each of these isomers  the axial C–Cl and C–H bonds, situated in the geminal position in relation to the oxygen atom, are longer, while the electron density at their Cl and H atoms is higher than in the corresponding equatorial bonds.

How to Cite
Feshin, V. P.; Zhizhina, L. I.; Feshina, E. V. Chem. Heterocycl. Compd. 2005, 41, 168. [Khim. Geterotsikl. Soedin. 2005, 196.]

For this article in the English edition, see DOI 10.1007/s10593-005-0121-8

 

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Published

2023-11-30

Issue

No. 2 (2005)

Section

Original Papers