Investigation of tautomeric behavior of 3-amino-4-[4-(dimethylamino)phenyl]-4,5-dihydro-1,2,5-thiadiazole 1,1-dioxide using Fourier Transform infrared and nuclear magnetic resonance spectroscopic methods: A density functional theory supported study

ERTÜRK A. G., Gümüş S., DİKMEN G., ALVER Ö.

CHEMICAL PHYSICS LETTERS, vol.661, pp.151-156, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 661
  • Publication Date: 2016
  • Doi Number: 10.1016/j.cplett.2016.08.047
  • Journal Name: CHEMICAL PHYSICS LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.151-156
  • Keywords: Sulfamide derivatives, Infrared spectroscopy, NMR spectroscopy, Tautomeric forms, IN-VITRO ANTIBACTERIAL, BIOLOGICAL EVALUATION, AB-INITIO, INHIBITORS, CHEMISTRY, SPECTRA, DESIGN, ENZYME
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

Sulfonamide derivatives have been widely incorporated in different types of studies, particularly in bioorganics and medicinal chemistry. Molecular conformation or tautomeric forms of molecules are directly related to their pharmaceutical and biological activities. In the scope of this work two possible tautomeric forms of 3-amino-4-[4-(dimethylamino)phenyl]-4,5-dihydro-1,2,5-thiadiazole 1,1-dioxide (C10R14N4O2S) molecule were tried to be identified by employing infrared and nuclear magnetic resonance spectroscopic methods. Obtained spectroscopic results suggest that 3-amino-4-[4-(diniethylamino)phenyl]-4,5-dihydro-1,2,5-thiadiazole 1,1-dioxide in its powder form shows the traces of both conformers (amino and imino) while in its liquid state in deuterated dimethyl sulfoxide it is mainly in imino form. (C) 2016 Elsevier B.V. All rights reserved.