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Journal of Structural Chemistry

, Volume 59, Issue 7, pp 1596–1609 | Cite as

Tautomerism in the Sulfonamide Moiety: Synthesis, Experimental and Theoretical Characterizations

  • Z. Ettehadi
  • A. Davoodnia
  • M. Khashi
  • S. Ali Beyramabadi
Article
  • 8 Downloads

Abstract

Following our previous work, we synthesized N-(7-methyl-5,6-diphenyl-2-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzensulfonamides to study the sulfonylimine-sulfonamide tautomerism. This goal is performed using the density functional theory (DFT). Four plausible isomers including the keto and enol sulfonamide as well as Z and E sulfonimide are considered for each of compounds. The DFT calculations are carried out at the B3LYP/6-31+G(d,p) level of theory. The optimized geometric parameters such as bond lengths and bond angles are calculated. The computed IR vibrational frequencies and 1H NMR chemical shifts are in good agreement with the experimental data. The structure of all compounds is confirmed on the basis of their full spectral data. In all three compounds, the Z-sulfonimide form is more stable than the other isomers. A high energy gap between the frontier orbitals confirms the stability of the compounds.

Keywords

pyrrolo[2,3-d]pyrimidine DMAP DFT tautomerism intramolecular proton transfer 

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Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • Z. Ettehadi
    • 1
  • A. Davoodnia
    • 1
  • M. Khashi
    • 2
  • S. Ali Beyramabadi
    • 1
  1. 1.Department of Chemistry, Mashhad BranchIslamic Azad UniversityMashhadIran
  2. 2.Young Researchers and Elite Club, Mashhad BranchIslamic Azad UniversityMashhadIran

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