Affordable Access

Publisher Website

Conformational equilibrium and intramolecular hydrogen bond of 4′X and 4X substituted 2′(OH)chalcones

Authors
Journal
Journal of Molecular Structure THEOCHEM
0166-1280
Publisher
Elsevier
Publication Date
Volume
493
Identifiers
DOI: 10.1016/s0166-1280(99)00239-0
Keywords
  • Conformational Equilibrium
  • Intramolecular Hydrogen Bond
  • Structure
  • 2′(Oh)
  • 4′X-Chalcones And 2′(Oh)
  • 4X-Chalcones
  • Calculations Am1
Disciplines
  • Physics

Abstract

Abstract By using the AM1 method on 4X and 4′X substituted 2′(OH)chalcones (X=H, OH, F, Cl, CH 3, CH 3O, N(CH 3) 2, and NO 2), certain currently unclear structural characteristics, conformational equilibria, intramolecular hydrogen bonds and UV spectroscopic properties had been clarified. The compounds studied have non-planar structures. The 2′(OH),4′Xchalcones only present the trans- s- cis conformation. trans- s- cis and trans- s- trans conformers of 2′(OH),4X-chalcones have a comparable thermodynamic stability. For these chalcones, a conformational equilibrium at 298 K exists, with 91% of the trans- s- cis form. The proposal of analyzing the intramolecular hydrogen bond of 2′(OH),4X-chalcones as an intramolecular proton-transfer reaction, is acceptable because the results and theoretical prediction of this study agree well with available UV spectroscopic experimental data.

There are no comments yet on this publication. Be the first to share your thoughts.