Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: Syntheses, crystal structures and melting points correlation

Autores
Di Salvo, Florencia; Camargo, Beatriz; García, Yolanda; Teixidor, Francesc; Viñas, Clara; Planas, José Giner; Light, Mark E.; Hursthouse, Michael B.
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The syntheses of new o-carboranyl alcohols bearing N-aromatic rings, 1-[R(hydroxy)methyl]-2-methyl-1,2-dicarba-closo-dodecaborane (R = 6-methyl-2-pyridyl 1b, 3-pyridyl 1c, 2-quinolyl 1e, 4-quinolyl 1f), 1-[R(hydroxy)methyl]-1,2-dicarba-closo-dodecaborane (R = 2-pyridyl 2a, 6-methyl-2-pyridyl 2b, 3-pyridyl 2c, 4-pyridyl 2d, 2-quinolyl 2e, 4-quinolyl 2f)), are reported. The crystal structures of all compounds, except that for 1b, are reported and compared with those related compounds previously synthesized by us (1-[R(hydroxy)methyl]-2-methyl-1,2-dicarba-closo-dodecaborane (R = 2-pyridyl 1a, 4-pyridyl 1d)). We provide an analysis of these compounds by means of X-ray crystallography, NMR/IR spectroscopies, thermal analyses and gas phase calculations in the context of crystal engineering. The results show that the crystal packings of these alcohols are dominated by the supramolecular O-H⋯N heterosynthon, but also include other weaker interactions such as C-H⋯O hydrogen bonds, H⋯H contacts and some degree of (C/B)-H⋯π interactions. There are four types of O-H⋯N hydrogen bonded chains, two giving rise to high melting point compounds (1c, 1d, 1f, 2c, 2d, and 2f) and two affording lower melting point compounds (1a, 2a and 2b). The lowest melting compounds (1e and 2e) show no such infinite O-H⋯N hydrogen bonding networks and only intramolecular O-H⋯N hydrogen bonds. We correlate the presence of the infinite O-H⋯N hydrogen bonding network in the crystal structure for the pyridine derivatives with their melting points. Gas phase calculations show that the energy for the O-H⋯N interactions in hydrogen bonded dimers is in the range 4-8 kcal mol-1.
Fil: Di Salvo, Florencia. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; España. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
Fil: Camargo, Beatriz. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; España
Fil: García, Yolanda. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; España
Fil: Teixidor, Francesc. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; España
Fil: Viñas, Clara. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; España
Fil: Planas, José Giner. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; España
Fil: Light, Mark E.. University of Southampton; Reino Unido
Fil: Hursthouse, Michael B.. University of Southampton; Reino Unido
Materia
Boron Clusters
O-Carboranylalcohols
Supremolecular Structure
Intermolecular Interactions
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/74334
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/74334
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: Syntheses, crystal structures and melting points correlationDi Salvo, FlorenciaCamargo, BeatrizGarcía, YolandaTeixidor, FrancescViñas, ClaraPlanas, José GinerLight, Mark E.Hursthouse, Michael B.Boron ClustersO-CarboranylalcoholsSupremolecular StructureIntermolecular Interactionshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The syntheses of new o-carboranyl alcohols bearing N-aromatic rings, 1-[R(hydroxy)methyl]-2-methyl-1,2-dicarba-closo-dodecaborane (R = 6-methyl-2-pyridyl 1b, 3-pyridyl 1c, 2-quinolyl 1e, 4-quinolyl 1f), 1-[R(hydroxy)methyl]-1,2-dicarba-closo-dodecaborane (R = 2-pyridyl 2a, 6-methyl-2-pyridyl 2b, 3-pyridyl 2c, 4-pyridyl 2d, 2-quinolyl 2e, 4-quinolyl 2f)), are reported. The crystal structures of all compounds, except that for 1b, are reported and compared with those related compounds previously synthesized by us (1-[R(hydroxy)methyl]-2-methyl-1,2-dicarba-closo-dodecaborane (R = 2-pyridyl 1a, 4-pyridyl 1d)). We provide an analysis of these compounds by means of X-ray crystallography, NMR/IR spectroscopies, thermal analyses and gas phase calculations in the context of crystal engineering. The results show that the crystal packings of these alcohols are dominated by the supramolecular O-H⋯N heterosynthon, but also include other weaker interactions such as C-H⋯O hydrogen bonds, H⋯H contacts and some degree of (C/B)-H⋯π interactions. There are four types of O-H⋯N hydrogen bonded chains, two giving rise to high melting point compounds (1c, 1d, 1f, 2c, 2d, and 2f) and two affording lower melting point compounds (1a, 2a and 2b). The lowest melting compounds (1e and 2e) show no such infinite O-H⋯N hydrogen bonding networks and only intramolecular O-H⋯N hydrogen bonds. We correlate the presence of the infinite O-H⋯N hydrogen bonding network in the crystal structure for the pyridine derivatives with their melting points. Gas phase calculations show that the energy for the O-H⋯N interactions in hydrogen bonded dimers is in the range 4-8 kcal mol-1.Fil: Di Salvo, Florencia. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; España. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; ArgentinaFil: Camargo, Beatriz. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; EspañaFil: García, Yolanda. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; EspañaFil: Teixidor, Francesc. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; EspañaFil: Viñas, Clara. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; EspañaFil: Planas, José Giner. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; EspañaFil: Light, Mark E.. University of Southampton; Reino UnidoFil: Hursthouse, Michael B.. University of Southampton; Reino UnidoRoyal Society of Chemistry2011-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/74334Di Salvo, Florencia; Camargo, Beatriz; García, Yolanda; Teixidor, Francesc; Viñas, Clara; et al.; Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: Syntheses, crystal structures and melting points correlation; Royal Society of Chemistry; CrystEngComm; 13; 19; 10-2011; 5788-58061466-8033CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/c1ce05449jinfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/Content/ArticleLanding/2011/CE/c1ce05449jinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:39:51Zoai:ri.conicet.gov.ar:11336/74334instacron: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 10:39:51.884CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: Syntheses, crystal structures and melting points correlation
title Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: Syntheses, crystal structures and melting points correlation
spellingShingle Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: Syntheses, crystal structures and melting points correlation
Di Salvo, Florencia
Boron Clusters
O-Carboranylalcohols
Supremolecular Structure
Intermolecular Interactions
title_short Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: Syntheses, crystal structures and melting points correlation
title_full Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: Syntheses, crystal structures and melting points correlation
title_fullStr Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: Syntheses, crystal structures and melting points correlation
title_full_unstemmed Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: Syntheses, crystal structures and melting points correlation
title_sort Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: Syntheses, crystal structures and melting points correlation
dc.creator.none.fl_str_mv Di Salvo, Florencia
Camargo, Beatriz
García, Yolanda
Teixidor, Francesc
Viñas, Clara
Planas, José Giner
Light, Mark E.
Hursthouse, Michael B.
author Di Salvo, Florencia
author_facet Di Salvo, Florencia
Camargo, Beatriz
García, Yolanda
Teixidor, Francesc
Viñas, Clara
Planas, José Giner
Light, Mark E.
Hursthouse, Michael B.
author_role author
author2 Camargo, Beatriz
García, Yolanda
Teixidor, Francesc
Viñas, Clara
Planas, José Giner
Light, Mark E.
Hursthouse, Michael B.
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Boron Clusters
O-Carboranylalcohols
Supremolecular Structure
Intermolecular Interactions
topic Boron Clusters
O-Carboranylalcohols
Supremolecular Structure
Intermolecular Interactions
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 syntheses of new o-carboranyl alcohols bearing N-aromatic rings, 1-[R(hydroxy)methyl]-2-methyl-1,2-dicarba-closo-dodecaborane (R = 6-methyl-2-pyridyl 1b, 3-pyridyl 1c, 2-quinolyl 1e, 4-quinolyl 1f), 1-[R(hydroxy)methyl]-1,2-dicarba-closo-dodecaborane (R = 2-pyridyl 2a, 6-methyl-2-pyridyl 2b, 3-pyridyl 2c, 4-pyridyl 2d, 2-quinolyl 2e, 4-quinolyl 2f)), are reported. The crystal structures of all compounds, except that for 1b, are reported and compared with those related compounds previously synthesized by us (1-[R(hydroxy)methyl]-2-methyl-1,2-dicarba-closo-dodecaborane (R = 2-pyridyl 1a, 4-pyridyl 1d)). We provide an analysis of these compounds by means of X-ray crystallography, NMR/IR spectroscopies, thermal analyses and gas phase calculations in the context of crystal engineering. The results show that the crystal packings of these alcohols are dominated by the supramolecular O-H⋯N heterosynthon, but also include other weaker interactions such as C-H⋯O hydrogen bonds, H⋯H contacts and some degree of (C/B)-H⋯π interactions. There are four types of O-H⋯N hydrogen bonded chains, two giving rise to high melting point compounds (1c, 1d, 1f, 2c, 2d, and 2f) and two affording lower melting point compounds (1a, 2a and 2b). The lowest melting compounds (1e and 2e) show no such infinite O-H⋯N hydrogen bonding networks and only intramolecular O-H⋯N hydrogen bonds. We correlate the presence of the infinite O-H⋯N hydrogen bonding network in the crystal structure for the pyridine derivatives with their melting points. Gas phase calculations show that the energy for the O-H⋯N interactions in hydrogen bonded dimers is in the range 4-8 kcal mol-1.
Fil: Di Salvo, Florencia. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; España. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
Fil: Camargo, Beatriz. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; España
Fil: García, Yolanda. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; España
Fil: Teixidor, Francesc. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; España
Fil: Viñas, Clara. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; España
Fil: Planas, José Giner. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de los Materiales de Barcelona; España
Fil: Light, Mark E.. University of Southampton; Reino Unido
Fil: Hursthouse, Michael B.. University of Southampton; Reino Unido
description The syntheses of new o-carboranyl alcohols bearing N-aromatic rings, 1-[R(hydroxy)methyl]-2-methyl-1,2-dicarba-closo-dodecaborane (R = 6-methyl-2-pyridyl 1b, 3-pyridyl 1c, 2-quinolyl 1e, 4-quinolyl 1f), 1-[R(hydroxy)methyl]-1,2-dicarba-closo-dodecaborane (R = 2-pyridyl 2a, 6-methyl-2-pyridyl 2b, 3-pyridyl 2c, 4-pyridyl 2d, 2-quinolyl 2e, 4-quinolyl 2f)), are reported. The crystal structures of all compounds, except that for 1b, are reported and compared with those related compounds previously synthesized by us (1-[R(hydroxy)methyl]-2-methyl-1,2-dicarba-closo-dodecaborane (R = 2-pyridyl 1a, 4-pyridyl 1d)). We provide an analysis of these compounds by means of X-ray crystallography, NMR/IR spectroscopies, thermal analyses and gas phase calculations in the context of crystal engineering. The results show that the crystal packings of these alcohols are dominated by the supramolecular O-H⋯N heterosynthon, but also include other weaker interactions such as C-H⋯O hydrogen bonds, H⋯H contacts and some degree of (C/B)-H⋯π interactions. There are four types of O-H⋯N hydrogen bonded chains, two giving rise to high melting point compounds (1c, 1d, 1f, 2c, 2d, and 2f) and two affording lower melting point compounds (1a, 2a and 2b). The lowest melting compounds (1e and 2e) show no such infinite O-H⋯N hydrogen bonding networks and only intramolecular O-H⋯N hydrogen bonds. We correlate the presence of the infinite O-H⋯N hydrogen bonding network in the crystal structure for the pyridine derivatives with their melting points. Gas phase calculations show that the energy for the O-H⋯N interactions in hydrogen bonded dimers is in the range 4-8 kcal mol-1.
publishDate 2011
dc.date.none.fl_str_mv 2011-10
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/11336/74334
Di Salvo, Florencia; Camargo, Beatriz; García, Yolanda; Teixidor, Francesc; Viñas, Clara; et al.; Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: Syntheses, crystal structures and melting points correlation; Royal Society of Chemistry; CrystEngComm; 13; 19; 10-2011; 5788-5806
1466-8033
CONICET Digital
CONICET
url http://hdl.handle.net/11336/74334
identifier_str_mv Di Salvo, Florencia; Camargo, Beatriz; García, Yolanda; Teixidor, Francesc; Viñas, Clara; et al.; Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: Syntheses, crystal structures and melting points correlation; Royal Society of Chemistry; CrystEngComm; 13; 19; 10-2011; 5788-5806
1466-8033
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/c1ce05449j
info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/Content/ArticleLanding/2011/CE/c1ce05449j
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
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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
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score 13.070432

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