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

TY - JOUR

T1 - The possible tautomerism of the potential rotary switch 2-(2-(2-Hydroxy-4-nitrophenyl)hydrazono)-1-phenylbutane-1,3-dione

AU - Hristova, Silvia

AU - Kamounah, Fadhil S

AU - Molla, Nevse

AU - Hansen, Poul Erik

AU - Nedeltcheva, Daniela

AU - Antonov, Liudmil

PY - 2017

Y1 - 2017

N2 - 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.

AB - 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.

KW - DFT

KW - Hydrazone

KW - NMR

KW - Rotary switch

KW - Tautomerism

KW - UV–Vis spectroscopy

U2 - 10.1016/j.dyepig.2017.05.021

DO - 10.1016/j.dyepig.2017.05.021

M3 - Journal article

AN - SCOPUS:85019863992

SN - 0143-7208

VL - 144

SP - 249

EP - 261

JO - Dyes and Pigments

JF - Dyes and Pigments

ER -