Tautomeric properties, conformations and structure of 2-hydroxyacetophenone methanesulfonylhydrazone


Alyar S., Ozmen U. O. , Karacan N., Şentürk O. S. , UDACHIN K. A.

JOURNAL OF MOLECULAR STRUCTURE, vol.889, pp.144-149, 2008 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 889
  • Publication Date: 2008
  • Doi Number: 10.1016/j.molstruc.2008.01.048
  • Title of Journal : JOURNAL OF MOLECULAR STRUCTURE
  • Page Numbers: pp.144-149

Abstract

The compound, 2-hydroxyacetophenone methanesulfonylhydrazone (apmsh) has been synthesized and its crystal structure has been investigated by X-ray analysis. The compound crystallizes in the monoclinic space group P21/c and the following unit cell parameters: a = 20.9496(15) angstrom, b = 4.9849(4) angstrom, c = 10.2300(8) angstrom; alpha = 90 degrees, beta = 98.2750(10)degrees, gamma = 90 degrees; V = 1057.21(14) angstrom 3 and Z = 1. The molecular geometry of the apmsh in the ground state has been calculated using the restricted Hartree-Fock with HF/6-31G** and density functional method with B3LYP/6-31G** basis set. The optimized bond lengths and bond angles obtained by using B3LYP/6-31G** are in better agreement with the experimental values than those by using RHF/6-31G**. The conformers located at minima by PM3 semi-empirical calculation were re-optimized by using B3LYP/6-31G** method. Quantum-chemical calculations indicate that enol-imine tautomeric form is favored and the most stable conformer in gas phase is approximately 6 kcal/mol stable than next conformer. (C) 2008 Elsevier B.V. All rights reserved.