Enol-imino-keto-enamine tautomerism in a diazepine derivative: How decisive are the intermolecular interactions in the equilibrium?
- Autores
- Rocha, Mariana; Gil, Diego Mauricio; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis; Ulic, Sonia Elizabeth
- Año de publicación
- 2019
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- The strange tautomeric equilibrium behaviour exhibited by a new o-hydroxyphenyl diazepine derivative, when the compound is analysed both in solution and solid state, open 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-enamino form in which the keto group integrate a cyclohexadienone moiety and the aromaticity of the phenol is loss, 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.
Fil: Rocha, Mariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Gil, Diego Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Piro, Oscar Enrique. Universidad Nacional de La Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Jios, Jorge Luis. Universidad Nacional de La Plata; Argentina. Comision de Investigaciones Cientificas de la Provincia de Buenos Aires. Unidad Plapimu Laseisic.; Argentina
Fil: Ulic, Sonia Elizabeth. Universidad Nacional de La Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina - Materia
-
O-HYDROXYPHENYL-1,4-DIAZEPINE
ENOL-IMINO-KETO-ENAMINE TAUTOMERISM
INTERMOLECULAR INTERACTIONS
STRUCTURAL STUDY - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/119057
Ver los metadatos del registro completo
id |
CONICETDig_8e35eddadba1aaf60ae2d3ccb6167857 |
---|---|
oai_identifier_str |
oai:ri.conicet.gov.ar:11336/119057 |
network_acronym_str |
CONICETDig |
repository_id_str |
3498 |
network_name_str |
CONICET Digital (CONICET) |
spelling |
Enol-imino-keto-enamine tautomerism in a diazepine derivative: How decisive are the intermolecular interactions in the equilibrium?Rocha, MarianaGil, Diego MauricioEcheverría, Gustavo AlbertoPiro, Oscar EnriqueJios, Jorge LuisUlic, Sonia ElizabethO-HYDROXYPHENYL-1,4-DIAZEPINEENOL-IMINO-KETO-ENAMINE TAUTOMERISMINTERMOLECULAR INTERACTIONSSTRUCTURAL STUDYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The strange tautomeric equilibrium behaviour exhibited by a new o-hydroxyphenyl diazepine derivative, when the compound is analysed both in solution and solid state, open 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-enamino form in which the keto group integrate a cyclohexadienone moiety and the aromaticity of the phenol is loss, 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.Fil: Rocha, Mariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaFil: Gil, Diego Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaFil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; ArgentinaFil: Piro, Oscar Enrique. Universidad Nacional de La Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; ArgentinaFil: Jios, Jorge Luis. Universidad Nacional de La Plata; Argentina. Comision de Investigaciones Cientificas de la Provincia de Buenos Aires. Unidad Plapimu Laseisic.; ArgentinaFil: Ulic, Sonia Elizabeth. Universidad Nacional de La Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaAmerican Chemical Society2019-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/119057Rocha, Mariana; Gil, Diego Mauricio; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis; et al.; Enol-imino-keto-enamine tautomerism in a diazepine derivative: How decisive are the intermolecular interactions in the equilibrium?; American Chemical Society; Journal of Organic Chemistry; 84; 17; 8-2019; 11042-110530022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/10.1021/acs.joc.9b01533info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.9b01533info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:40:33Zoai:ri.conicet.gov.ar:11336/119057instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:40:33.347CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Enol-imino-keto-enamine tautomerism in a diazepine derivative: How decisive are the intermolecular interactions in the equilibrium? |
title |
Enol-imino-keto-enamine tautomerism in a diazepine derivative: How decisive are the intermolecular interactions in the equilibrium? |
spellingShingle |
Enol-imino-keto-enamine tautomerism in a diazepine derivative: How decisive are the intermolecular interactions in the equilibrium? Rocha, Mariana O-HYDROXYPHENYL-1,4-DIAZEPINE ENOL-IMINO-KETO-ENAMINE TAUTOMERISM INTERMOLECULAR INTERACTIONS STRUCTURAL STUDY |
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? |
dc.creator.none.fl_str_mv |
Rocha, Mariana Gil, Diego Mauricio Echeverría, Gustavo Alberto Piro, Oscar Enrique Jios, Jorge Luis Ulic, Sonia Elizabeth |
author |
Rocha, Mariana |
author_facet |
Rocha, Mariana Gil, Diego Mauricio Echeverría, Gustavo Alberto Piro, Oscar Enrique Jios, Jorge Luis Ulic, Sonia Elizabeth |
author_role |
author |
author2 |
Gil, Diego Mauricio Echeverría, Gustavo Alberto Piro, Oscar Enrique Jios, Jorge Luis Ulic, Sonia Elizabeth |
author2_role |
author author author author author |
dc.subject.none.fl_str_mv |
O-HYDROXYPHENYL-1,4-DIAZEPINE ENOL-IMINO-KETO-ENAMINE TAUTOMERISM INTERMOLECULAR INTERACTIONS STRUCTURAL STUDY |
topic |
O-HYDROXYPHENYL-1,4-DIAZEPINE ENOL-IMINO-KETO-ENAMINE TAUTOMERISM INTERMOLECULAR INTERACTIONS STRUCTURAL STUDY |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
The strange tautomeric equilibrium behaviour exhibited by a new o-hydroxyphenyl diazepine derivative, when the compound is analysed both in solution and solid state, open 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-enamino form in which the keto group integrate a cyclohexadienone moiety and the aromaticity of the phenol is loss, 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. Fil: Rocha, Mariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina Fil: Gil, Diego Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina Fil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina Fil: Piro, Oscar Enrique. Universidad Nacional de La Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina Fil: Jios, Jorge Luis. Universidad Nacional de La Plata; Argentina. Comision de Investigaciones Cientificas de la Provincia de Buenos Aires. Unidad Plapimu Laseisic.; Argentina Fil: Ulic, Sonia Elizabeth. Universidad Nacional de La Plata; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina |
description |
The strange tautomeric equilibrium behaviour exhibited by a new o-hydroxyphenyl diazepine derivative, when the compound is analysed both in solution and solid state, open 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-enamino form in which the keto group integrate a cyclohexadienone moiety and the aromaticity of the phenol is loss, 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. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-08 |
dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion 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://hdl.handle.net/11336/119057 Rocha, Mariana; Gil, Diego Mauricio; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis; et al.; Enol-imino-keto-enamine tautomerism in a diazepine derivative: How decisive are the intermolecular interactions in the equilibrium?; American Chemical Society; Journal of Organic Chemistry; 84; 17; 8-2019; 11042-11053 0022-3263 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/119057 |
identifier_str_mv |
Rocha, Mariana; Gil, Diego Mauricio; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis; et al.; Enol-imino-keto-enamine tautomerism in a diazepine derivative: How decisive are the intermolecular interactions in the equilibrium?; American Chemical Society; Journal of Organic Chemistry; 84; 17; 8-2019; 11042-11053 0022-3263 CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/10.1021/acs.joc.9b01533 info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.9b01533 |
dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
eu_rights_str_mv |
openAccess |
rights_invalid_str_mv |
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
dc.format.none.fl_str_mv |
application/pdf application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
American Chemical Society |
publisher.none.fl_str_mv |
American Chemical Society |
dc.source.none.fl_str_mv |
reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
reponame_str |
CONICET Digital (CONICET) |
collection |
CONICET Digital (CONICET) |
instname_str |
Consejo Nacional de Investigaciones Científicas y Técnicas |
repository.name.fl_str_mv |
CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
repository.mail.fl_str_mv |
dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar |
_version_ |
1844613283215048704 |
score |
13.070432 |