The possible tautomerism of the potential rotary switch 2-(2-(2-Hydroxy-4-nitrophenyl)hydrazono)-1-phenylbutane-1,3-dione

Silvia Hristova, Fadhil S. Kamounah, Nevse Molla, Poul Erik Hansen, Daniela Nedeltcheva, Liudmil Antonov

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Abstract

The title compound is potentially tautomeric and its tautomerism was studied by means of molecular spectroscopy (1H and 13C NMR and UV–Vis) in DMSO as well as by quantum chemical calculations (M06-2X/TZVP). The detailed assignment of the NMR signals supported by the theoretical calculations clearly shows that the previous interpretation, available in the literature, about the coexistence of two tautomeric forms is not correct. The compound exists as major and minor isomer of a single tautomeric form. In addition, a 2-methoxy derivative (the OH group replaced by a methoxy group) is also investigated and show similar trends.
OriginalsprogEngelsk
TidsskriftDyes and Pigments
Vol/bind144
Sider (fra-til)249-261
Antal sider13
ISSN0143-7208
DOI
StatusUdgivet - 2017

Emneord

  • isotope effects
  • UV
  • DFT calculations
  • solvent effects
  • rotary switch

Citer dette