Tautomeric properties, conformations and structure of 2-hydroxyacetophenone methanesulfonylhydrazone

S. Alyar, Ü Özdemir Özmen, N. Karacan*, O. Ş Şentürk, K. A. Udachin

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

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) Å, b = 4.9849(4) Å, c = 10.2300(8) Å; α = 90°, β = 98.2750(10)°, γ = 90°; V = 1057.21(14) Å3 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.

Original languageEnglish
Pages (from-to)144-149
Number of pages6
JournalJournal of Molecular Structure
Volume889
Issue number1-3
DOIs
Publication statusPublished - 29 Oct 2008

Funding

This research was supported by TUBITAK Research Fund under Project No: 104T390. We thanks Steacie Institute for Molecular Sciences for X-ray.

FundersFunder number
TUBITAK Research Fund104T390

    Keywords

    • Conformational analysis
    • Crystal structure
    • DFT
    • HF
    • Sulfonyl hydrazone
    • Tautomerism

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