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

doi:10.1016/j.dyepig.2017.05.021

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 tidsskrift › Tidsskriftartikel › Forskning › peer 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.

Originalsprog	Engelsk
Tidsskrift	Dyes and Pigments
Vol/bind	144
Sider (fra-til)	249-261
Antal sider	13
ISSN	0143-7208
DOI	https://doi.org/10.1016/j.dyepig.2017.05.021
Status	Udgivet - 2017

Emneord

DFT calculations
UV
isotope effects
rotary switch
solvent effects

Link til dokument

10.1016/j.dyepig.2017.05.021

Citer dette

@article{33946c362643462e86618aa939dd741d,

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

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.",

keywords = "DFT calculations, UV, isotope effects, rotary switch, solvent effects, DFT calculations, NMR, UV–Vis spectroscopy, hydrazone, isotope effects, rotary switch, tautomerism",

author = "Silvia Hristova and Kamounah, {Fadhil S.} and Nevse Molla and Hansen, {Poul Erik} and Daniela Nedeltcheva and Liudmil Antonov",

year = "2017",

doi = "10.1016/j.dyepig.2017.05.021",

language = "English",

volume = "144",

pages = "249--261",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Pergamon Press",

}

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 calculations

KW - UV

KW - isotope effects

KW - rotary switch

KW - solvent effects

KW - DFT calculations

KW - NMR

KW - UV–Vis spectroscopy

KW - hydrazone

KW - isotope effects

KW - rotary switch

KW - tautomerism

U2 - 10.1016/j.dyepig.2017.05.021

DO - 10.1016/j.dyepig.2017.05.021

M3 - Journal article

SN - 0143-7208

VL - 144

SP - 249

EP - 261

JO - Dyes and Pigments

JF - Dyes and Pigments

ER -