Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring

Two novel tetrafluorinated 1,5-benzodiazepinones were synthesized and their X-ray structures determined. 6,7,8,9-Tetrafluoro-4- methyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one crystallizes in the monoclinic P21/c space group and 6,7,8,9-tetrafluoro-1,4- dimethyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one...

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Autores: Pérez-Torralba, Marta, Claramunt, Rosa M., García, M. Ángeles, López, Concepción, Torralba, M. Carmen, Torres, M. Rosario, Alkorta, Ibon, Elguero, José
Tipo de recurso: artículo
Fecha de publicación:2013
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/89134
Acceso en línea:http://hdl.handle.net/10261/89134
Access Level:acceso abierto
Palabra clave:Benzodiazepinones
DFT
GIAO calculations
inversion barriers
multinuclear NMR
tautomerism
X-ray structures
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spelling Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ringPérez-Torralba, MartaClaramunt, Rosa M.García, M. ÁngelesLópez, ConcepciónTorralba, M. CarmenTorres, M. RosarioAlkorta, IbonElguero, JoséBenzodiazepinonesDFTGIAO calculationsinversion barriersmultinuclear NMRtautomerismX-ray structuresTwo novel tetrafluorinated 1,5-benzodiazepinones were synthesized and their X-ray structures determined. 6,7,8,9-Tetrafluoro-4- methyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one crystallizes in the monoclinic P21/c space group and 6,7,8,9-tetrafluoro-1,4- dimethyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one in the triclinic P−1 space group. Density functional theory studies at the B3LYP/6-311++G(d,p) level were carried out on these compounds and on four non-fluorinated derivatives, allowing to calculate geometries, tautomeric energies and ring-inversion barriers, that were compared with the experimental results obtained by static and dynamic NMR in solution and in solid state.This work has been financed by the Spanish MICINN (CTQ2009-13129-C02-02 and CTQ2010-16122) and by the Comunidad Autónoma de Madrid (Project MADRISOLAR2, ref S2009/PPQ-1533)Peer reviewedBeilstein-Institut für Literatur der Organischen Chemie201420142013info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501http://hdl.handle.net/10261/89134reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttp://dx.doi.org/10.3762/bjoc.9.253info:eu-repo/semantics/openAccessoai:digital.csic.es:10261/891342026-05-22T06:33:51Z
dc.title.none.fl_str_mv Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring
title Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring
spellingShingle Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring
Pérez-Torralba, Marta
Benzodiazepinones
DFT
GIAO calculations
inversion barriers
multinuclear NMR
tautomerism
X-ray structures
title_short Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring
title_full Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring
title_fullStr Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring
title_full_unstemmed Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring
title_sort Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring
dc.creator.none.fl_str_mv Pérez-Torralba, Marta
Claramunt, Rosa M.
García, M. Ángeles
López, Concepción
Torralba, M. Carmen
Torres, M. Rosario
Alkorta, Ibon
Elguero, José
author Pérez-Torralba, Marta
author_facet Pérez-Torralba, Marta
Claramunt, Rosa M.
García, M. Ángeles
López, Concepción
Torralba, M. Carmen
Torres, M. Rosario
Alkorta, Ibon
Elguero, José
author_role author
author2 Claramunt, Rosa M.
García, M. Ángeles
López, Concepción
Torralba, M. Carmen
Torres, M. Rosario
Alkorta, Ibon
Elguero, José
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Benzodiazepinones
DFT
GIAO calculations
inversion barriers
multinuclear NMR
tautomerism
X-ray structures
topic Benzodiazepinones
DFT
GIAO calculations
inversion barriers
multinuclear NMR
tautomerism
X-ray structures
description Two novel tetrafluorinated 1,5-benzodiazepinones were synthesized and their X-ray structures determined. 6,7,8,9-Tetrafluoro-4- methyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one crystallizes in the monoclinic P21/c space group and 6,7,8,9-tetrafluoro-1,4- dimethyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one in the triclinic P−1 space group. Density functional theory studies at the B3LYP/6-311++G(d,p) level were carried out on these compounds and on four non-fluorinated derivatives, allowing to calculate geometries, tautomeric energies and ring-inversion barriers, that were compared with the experimental results obtained by static and dynamic NMR in solution and in solid state.
publishDate 2013
dc.date.none.fl_str_mv 2013
2014
2014
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/89134
url http://hdl.handle.net/10261/89134
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv http://dx.doi.org/10.3762/bjoc.9.253
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Beilstein-Institut für Literatur der Organischen Chemie
publisher.none.fl_str_mv Beilstein-Institut für Literatur der Organischen Chemie
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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