Tautomeric properties, conformations and structure of 2-hydroxyacetophenone methanesulfonylhydrazone

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

doi:10.1016/j.molstruc.2008.01.048

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

26 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 language	English
Pages (from-to)	144-149
Number of pages	6
Journal	Journal of Molecular Structure
Volume	889
Issue number	1-3
DOIs	https://doi.org/10.1016/j.molstruc.2008.01.048
Publication status	Published - 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.

Funders	Funder number
TUBITAK Research Fund	104T390

Keywords

Conformational analysis
Crystal structure
DFT
HF
Sulfonyl hydrazone
Tautomerism

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10.1016/j.molstruc.2008.01.048

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title = "Tautomeric properties, conformations and structure of 2-hydroxyacetophenone methanesulfonylhydrazone",

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) {\AA}, b = 4.9849(4) {\AA}, c = 10.2300(8) {\AA}; α = 90°, β = 98.2750(10)°, γ = 90°; V = 1057.21(14) {\AA}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.",

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AU - Alyar, S.

AU - Özmen, Ü Özdemir

AU - Karacan, N.

AU - Şentürk, O. Ş

AU - Udachin, K. A.

PY - 2008/10/29

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N2 - 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.

AB - 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.

KW - Conformational analysis

KW - Crystal structure

KW - DFT

KW - HF

KW - Sulfonyl hydrazone

KW - Tautomerism

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Tautomeric properties, conformations and structure of 2-hydroxyacetophenone methanesulfonylhydrazone

Abstract

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