Enol-imino−Keto-enamine Tautomerism in a Diazepine Derivative: How Decisive Are the Intermolecular Interactions in the Equilibrium?

The strange tautomeric equilibrium behavior exhibited by a new o-hydroxyphenyl diazepine derivative when the compound is analyzed both in solution and solid state opens the structural study of the enol-imino-keto-enamine forms and the influence of the intermolecular interactions in their equilibrium...

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Autores principales: Rocha, Mariana, Gil, Diego Mauricio, Echeverría, Gustavo Alberto, Piro, Oscar Enrique, Jios, Jorge Luis, Ulic, Sonia Elizabeth
Formato: Articulo
Lenguaje:Inglés
Publicado: 2019
Materias:
Ciencias Exactas
Física
Química
diazepine derivative
tautomerism
NMR spectroscopy
molecular interactions
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/124102
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-124102
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Ciencias Exactas
Física
Química
diazepine derivative
tautomerism
NMR spectroscopy
molecular interactions
spellingShingle Ciencias Exactas
Física
Química
diazepine derivative
tautomerism
NMR spectroscopy
molecular interactions
Rocha, Mariana
Gil, Diego Mauricio
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
Ulic, Sonia Elizabeth
Enol-imino−Keto-enamine Tautomerism in a Diazepine Derivative: How Decisive Are the Intermolecular Interactions in the Equilibrium?
topic_facet Ciencias Exactas
Física
Química
diazepine derivative
tautomerism
NMR spectroscopy
molecular interactions
description The strange tautomeric equilibrium behavior exhibited by a new o-hydroxyphenyl diazepine derivative when the compound is analyzed both in solution and solid state opens the structural study of the enol-imino-keto-enamine forms and the influence of the intermolecular interactions in their equilibrium. The expected enol-imino form, in which the enol is part of a phenyl system and a strong O-H···N intramolecular hydrogen bond is established, results the most stable tautomer in gas phase (theoretical calculations) and was detected by NMR spectroscopy when the compound was dissolved in aprotic solvents. Nevertheless, the keto-enamine form, in which the keto group integrates a cyclohexadienone moiety and the aromaticity of the phenol is lost, was the only tautomer in the crystal lattice according to single-crystal X-ray diffraction, vibrational spectroscopy, and diffuse reflectance results. The last form was also found as the main tautomer in UV-vis and NMR spectroscopy when a protic solvent was employed.
format Articulo
Articulo
author Rocha, Mariana
Gil, Diego Mauricio
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
Ulic, Sonia Elizabeth
author_facet Rocha, Mariana
Gil, Diego Mauricio
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
Ulic, Sonia Elizabeth
author_sort Rocha, Mariana
title Enol-imino−Keto-enamine Tautomerism in a Diazepine Derivative: How Decisive Are the Intermolecular Interactions in the Equilibrium?
title_short Enol-imino−Keto-enamine Tautomerism in a Diazepine Derivative: How Decisive Are the Intermolecular Interactions in the Equilibrium?
title_full Enol-imino−Keto-enamine Tautomerism in a Diazepine Derivative: How Decisive Are the Intermolecular Interactions in the Equilibrium?
title_fullStr Enol-imino−Keto-enamine Tautomerism in a Diazepine Derivative: How Decisive Are the Intermolecular Interactions in the Equilibrium?
title_full_unstemmed Enol-imino−Keto-enamine Tautomerism in a Diazepine Derivative: How Decisive Are the Intermolecular Interactions in the Equilibrium?
title_sort enol-imino−keto-enamine tautomerism in a diazepine derivative: how decisive are the intermolecular interactions in the equilibrium?
publishDate 2019
url http://sedici.unlp.edu.ar/handle/10915/124102
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bdutipo_str Repositorios
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