Hydrogen Bonds, Tautomers, and Conformation in 2-Hydroxyphenyl 2-hydroxy-2-(β-naphthyl)vinyl Ketone

Single crystal X-ray diffraction and IR spectroscopy have been used to study the conformation of 2-hydroxyphenyl 2-hydroxy-2-(α-naphthyl)vinyl ketone in solid state. It was found that one of the two possible enol tautomeric forms is stabilized in the crystal. The 1-hydroxy-3-oxo-1,3-propenylene moie...

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Detalles Bibliográficos
Autores principales: Echeverría, Gustavo Alberto, Jios, Jorge Luis, Autino, Juan Carlos, Punte, Graciela María del Carmen
Formato: Articulo
Lenguaje:Español
Publicado: 2000
Materias:
Química
Keto-enol tautomerism
single crystal X-ray diffraction
intra- and intermolecular hydrogen bond
resonance-assisted hydrogen bonds
IR data
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/133521
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-133521
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Español
topic Química
Keto-enol tautomerism
single crystal X-ray diffraction
intra- and intermolecular hydrogen bond
resonance-assisted hydrogen bonds
IR data
spellingShingle Química
Keto-enol tautomerism
single crystal X-ray diffraction
intra- and intermolecular hydrogen bond
resonance-assisted hydrogen bonds
IR data
Echeverría, Gustavo Alberto
Jios, Jorge Luis
Autino, Juan Carlos
Punte, Graciela María del Carmen
Hydrogen Bonds, Tautomers, and Conformation in 2-Hydroxyphenyl 2-hydroxy-2-(β-naphthyl)vinyl Ketone
topic_facet Química
Keto-enol tautomerism
single crystal X-ray diffraction
intra- and intermolecular hydrogen bond
resonance-assisted hydrogen bonds
IR data
description Single crystal X-ray diffraction and IR spectroscopy have been used to study the conformation of 2-hydroxyphenyl 2-hydroxy-2-(α-naphthyl)vinyl ketone in solid state. It was found that one of the two possible enol tautomeric forms is stabilized in the crystal. The 1-hydroxy-3-oxo-1,3-propenylene moiety, O=C—CH=C—OH, shows a strong intramolecular H bond with a definite character of reasonance-assisted hydrogen bond in spite of being in competition with ring intermolecular hydrogen bonds. The comparison of the present results with solution NMR data indicates that the molecular geometry in solid state and in solution are similar.
format Articulo
Articulo
author Echeverría, Gustavo Alberto
Jios, Jorge Luis
Autino, Juan Carlos
Punte, Graciela María del Carmen
author_facet Echeverría, Gustavo Alberto
Jios, Jorge Luis
Autino, Juan Carlos
Punte, Graciela María del Carmen
author_sort Echeverría, Gustavo Alberto
title Hydrogen Bonds, Tautomers, and Conformation in 2-Hydroxyphenyl 2-hydroxy-2-(β-naphthyl)vinyl Ketone
title_short Hydrogen Bonds, Tautomers, and Conformation in 2-Hydroxyphenyl 2-hydroxy-2-(β-naphthyl)vinyl Ketone
title_full Hydrogen Bonds, Tautomers, and Conformation in 2-Hydroxyphenyl 2-hydroxy-2-(β-naphthyl)vinyl Ketone
title_fullStr Hydrogen Bonds, Tautomers, and Conformation in 2-Hydroxyphenyl 2-hydroxy-2-(β-naphthyl)vinyl Ketone
title_full_unstemmed Hydrogen Bonds, Tautomers, and Conformation in 2-Hydroxyphenyl 2-hydroxy-2-(β-naphthyl)vinyl Ketone
title_sort hydrogen bonds, tautomers, and conformation in 2-hydroxyphenyl 2-hydroxy-2-(β-naphthyl)vinyl ketone
publishDate 2000
url http://sedici.unlp.edu.ar/handle/10915/133521
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AT jiosjorgeluis hydrogenbondstautomersandconformationin2hydroxyphenyl2hydroxy2bnaphthylvinylketone
AT autinojuancarlos hydrogenbondstautomersandconformationin2hydroxyphenyl2hydroxy2bnaphthylvinylketone
AT puntegracielamariadelcarmen hydrogenbondstautomersandconformationin2hydroxyphenyl2hydroxy2bnaphthylvinylketone
bdutipo_str Repositorios
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