Structural Chemistry

, Volume 21, Issue 5, pp 1005–1011

Intramolecular S···O chalcogen bond in thioindirubin

  • Oleg V. Shishkin
  • Irina V. Omelchenko
  • Andrei L. Kalyuzhny
  • Boris V. Paponov
Original Research

DOI: 10.1007/s11224-010-9638-2

Cite this article as:
Shishkin, O.V., Omelchenko, I.V., Kalyuzhny, A.L. et al. Struct Chem (2010) 21: 1005. doi:10.1007/s11224-010-9638-2

Abstract

Results of X-ray diffraction study and quantum-chemical calculations revealed that molecular conformation of thioindirubin molecule creates suitable conditions for formation of intramolecular C–H···O and S···O interactions. Analysis of molecular electrostatic potential (MEP) demonstrates existence of two areas of positive MEP (σ-holes) in the outermost part of the sulfur atom on the continuation of the lines of the C–S bonds. One of these σ-holes is oriented toward region of negative MEP around the oxygen atom of carbonyl group. Such situation corresponds to formation of σ-hole or chalcogen bond. Existence of both types of bonding interactions is confirmed by topological analysis of electron density distribution using “Atoms in Molecules” (AIM) theory. Energies of the C–H···O hydrogen bond and the S···O σ-hole bond derived from AIM and NBO theories are very close.

Keywords

Thioindirubin X-ray diffraction study σ-hole bonding AIM NBO MEP 

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Oleg V. Shishkin
    • 1
    • 2
  • Irina V. Omelchenko
    • 1
  • Andrei L. Kalyuzhny
    • 2
  • Boris V. Paponov
    • 2
  1. 1.STC “Institute for Single Crystals”, National Academy of Science of UkraineKharkivUkraine
  2. 2.V. M. Karazin Kharkiv National UniversityKharkivUkraine

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