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

Autores
Echeverría, Gustavo Alberto; Jios, Jorge Luis; Autino, Juan Carlos; Punte, Graciela María del Carmen
Año de publicación
2000
Idioma
español castellano
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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.
Facultad de Ciencias Exactas
Materia
Química
Keto-enol tautomerism
single crystal X-ray diffraction
intra- and intermolecular hydrogen bond
resonance-assisted hydrogen bonds
IR data
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/133521
Acceder
id SEDICI_5e22560fb630c7e36de8f7a4d6efee2b
oai_identifier_str oai:sedici.unlp.edu.ar:10915/133521
network_acronym_str SEDICI
repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling Hydrogen Bonds, Tautomers, and Conformation in 2-Hydroxyphenyl 2-hydroxy-2-(β-naphthyl)vinyl KetoneEcheverría, Gustavo AlbertoJios, Jorge LuisAutino, Juan CarlosPunte, Graciela María del CarmenQuímicaKeto-enol tautomerismsingle crystal X-ray diffractionintra- and intermolecular hydrogen bondresonance-assisted hydrogen bondsIR dataSingle 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.Facultad de Ciencias Exactas2000info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf367-373http://sedici.unlp.edu.ar/handle/10915/133521spainfo:eu-repo/semantics/altIdentifier/issn/1040-0400info:eu-repo/semantics/altIdentifier/issn/1572-9001info:eu-repo/semantics/altIdentifier/doi/10.1023/a:1026522105977info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/Creative Commons Attribution 4.0 International (CC BY 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-29T11:31:47Zoai:sedici.unlp.edu.ar:10915/133521Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-29 11:31:47.28SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv Hydrogen Bonds, Tautomers, and Conformation in 2-Hydroxyphenyl 2-hydroxy-2-(β-naphthyl)vinyl Ketone
title Hydrogen Bonds, Tautomers, and Conformation in 2-Hydroxyphenyl 2-hydroxy-2-(β-naphthyl)vinyl Ketone
spellingShingle Hydrogen Bonds, Tautomers, and Conformation in 2-Hydroxyphenyl 2-hydroxy-2-(β-naphthyl)vinyl Ketone
Echeverría, Gustavo Alberto
Química
Keto-enol tautomerism
single crystal X-ray diffraction
intra- and intermolecular hydrogen bond
resonance-assisted hydrogen bonds
IR data
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
dc.creator.none.fl_str_mv Echeverría, Gustavo Alberto
Jios, Jorge Luis
Autino, Juan Carlos
Punte, Graciela María del Carmen
author Echeverría, Gustavo Alberto
author_facet Echeverría, Gustavo Alberto
Jios, Jorge Luis
Autino, Juan Carlos
Punte, Graciela María del Carmen
author_role author
author2 Jios, Jorge Luis
Autino, Juan Carlos
Punte, Graciela María del Carmen
author2_role author
author
author
dc.subject.none.fl_str_mv Química
Keto-enol tautomerism
single crystal X-ray diffraction
intra- and intermolecular hydrogen bond
resonance-assisted hydrogen bonds
IR data
topic Química
Keto-enol tautomerism
single crystal X-ray diffraction
intra- and intermolecular hydrogen bond
resonance-assisted hydrogen bonds
IR data
dc.description.none.fl_txt_mv 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.
Facultad de Ciencias Exactas
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.
publishDate 2000
dc.date.none.fl_str_mv 2000
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Articulo
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://sedici.unlp.edu.ar/handle/10915/133521
url http://sedici.unlp.edu.ar/handle/10915/133521
dc.language.none.fl_str_mv spa
language spa
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/1040-0400
info:eu-repo/semantics/altIdentifier/issn/1572-9001
info:eu-repo/semantics/altIdentifier/doi/10.1023/a:1026522105977
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
dc.format.none.fl_str_mv application/pdf
367-373
dc.source.none.fl_str_mv reponame:SEDICI (UNLP)
instname:Universidad Nacional de La Plata
instacron:UNLP
reponame_str SEDICI (UNLP)
collection SEDICI (UNLP)
instname_str Universidad Nacional de La Plata
instacron_str UNLP
institution UNLP
repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
repository.mail.fl_str_mv alira@sedici.unlp.edu.ar
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score 13.070432

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