MOLECULAR STRUCTURE OF COMPLEXES WITH A BIFURCATED HYDROGEN BOND. 5. DIMERS OF 3-HYDROXY-2-METHYL-4-PYRONE IN INERT MEDIA

Authors

  • С. А. Муха A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk
  • Н. Н. Чипанина A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk
  • И. В. Стерхова A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk
  • Т. Н. Аксаментова A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk
  • С. А. Медведева A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk
  • В. К. Турчанинов A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk

DOI:

https://doi.org/10.1007/7740

Keywords:

3-hydroxy-2-methyl-4-pyrone, dimers, maltol, bifurcated hydrogen bond, DFT quantum-chemical calculations, IR spectra

Abstract

According to the data from IR spectroscopy  and quantum-chemical calculations (B3LYP/6-31G**, B3LYP/6-311G*), in the vapor and in dichloroethane the synperiplanar conformer of 3-hydroxy-2-methyl-4-pyrone (maltol) exists in equilibrium with two types of dimers. The hydrogen atom of the hydroxy group of one them participates in the formation of a three-center bifurcated hydrogen bond. The second isomer is formed by means of two such H  bonds, the intramolecular component of which is substantially weakened while the intermolecular component is so strong that it approximates in character to a two-center hydrogen bond.

How to Cite
Mukha, S. A.; Chipanina, N. N.; Sterkhova, I. V.; Aksamentova, T. N.; Medvedeva, S. A.; Turchaninov, V. K.  Chem. Heterocycl. Compd. 2006, 42, 1404. [Khim. Geterotsikl. Soedin. 2006, 1635.]

For this article in the English edition see DOI 10.1007/s10593-006-0256-2


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Published

2023-04-25

Issue

No. 11 (2006)

Section

Original Papers