Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols

Autores
Tsang, Min Ying; Di Salvo, Florencia; Teixidor, Francesc; Viñas, Clara; Planas, José Giner; Choquesillo Lazarte, Duane; Vanthuyne, Nicolas
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Ten structurally related racemic 2-pyridylmethyl alcohols containing an o-carborane core (1,2-closo-C2B10H10; rac-1a) or m-carborane (1,7-closo-C2B10H10; rac-2a) or p-carborane (1,7-closo-C2B10H10; rac-3a) and their enantiopure forms (R- and S-1a or R- and S-2a or R- and S-3a), as well as an iodo derivative of rac-3a (rac-4a) and a non-carborane derivative (C6H5; rac-5) have been studied by single crystal X-ray crystallography. All racemic and enantiopure structures show O-H⋯N hydrogen bonded homochiral 21-helical networks, except that for rac-3a, which forms O-H⋯N hydrogen bonded trimers. A comparison of these X-ray structures with that for others found in the Cambridge Structural Database for chiral 2-pyridyl alcohols-either in racemic or enantiopure forms-that form O-H⋯N hydrogen bonded homochiral 21-helical networks reveals a possible relationship between the torsion angle of the hydrogen bond donor and acceptor groups in these molecules and the hydrogen bonded supramolecular helices formed in the solid state.
Fil: Tsang, Min Ying. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de Los Materiales de Barcelona; España
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: 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: Choquesillo Lazarte, Duane. Universidad de Granada; España. Consejo Superior de Investigaciones Científicas; España
Fil: Vanthuyne, Nicolas. Aix Marseille Universite; Francia
Materia
Molecular Chirality
Carborane
Supramolecular Chirality
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:11336/37614
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/37614
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcoholsTsang, Min YingDi Salvo, FlorenciaTeixidor, FrancescViñas, ClaraPlanas, José GinerChoquesillo Lazarte, DuaneVanthuyne, NicolasMolecular ChiralityCarboraneSupramolecular Chiralityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Ten structurally related racemic 2-pyridylmethyl alcohols containing an o-carborane core (1,2-closo-C2B10H10; rac-1a) or m-carborane (1,7-closo-C2B10H10; rac-2a) or p-carborane (1,7-closo-C2B10H10; rac-3a) and their enantiopure forms (R- and S-1a or R- and S-2a or R- and S-3a), as well as an iodo derivative of rac-3a (rac-4a) and a non-carborane derivative (C6H5; rac-5) have been studied by single crystal X-ray crystallography. All racemic and enantiopure structures show O-H⋯N hydrogen bonded homochiral 21-helical networks, except that for rac-3a, which forms O-H⋯N hydrogen bonded trimers. A comparison of these X-ray structures with that for others found in the Cambridge Structural Database for chiral 2-pyridyl alcohols-either in racemic or enantiopure forms-that form O-H⋯N hydrogen bonded homochiral 21-helical networks reveals a possible relationship between the torsion angle of the hydrogen bond donor and acceptor groups in these molecules and the hydrogen bonded supramolecular helices formed in the solid state.Fil: Tsang, Min Ying. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de Los Materiales de Barcelona; EspañaFil: 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: 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: Choquesillo Lazarte, Duane. Universidad de Granada; España. Consejo Superior de Investigaciones Científicas; EspañaFil: Vanthuyne, Nicolas. Aix Marseille Universite; FranciaAmerican Chemical Society2015-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/37614Tsang, Min Ying; Di Salvo, Florencia; Teixidor, Francesc; Viñas, Clara; Planas, José Giner; et al.; Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols; American Chemical Society; Crystal Growth & Design; 15; 2; 2-2015; 935-9451528-7483CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/cg501748xinfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/cg501748xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-05T10:34:53Zoai:ri.conicet.gov.ar:11336/37614instacron: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:34982025-11-05 10:34:54.118CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols
title Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols
spellingShingle Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols
Tsang, Min Ying
Molecular Chirality
Carborane
Supramolecular Chirality
title_short Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols
title_full Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols
title_fullStr Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols
title_full_unstemmed Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols
title_sort Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols
dc.creator.none.fl_str_mv Tsang, Min Ying
Di Salvo, Florencia
Teixidor, Francesc
Viñas, Clara
Planas, José Giner
Choquesillo Lazarte, Duane
Vanthuyne, Nicolas
author Tsang, Min Ying
author_facet Tsang, Min Ying
Di Salvo, Florencia
Teixidor, Francesc
Viñas, Clara
Planas, José Giner
Choquesillo Lazarte, Duane
Vanthuyne, Nicolas
author_role author
author2 Di Salvo, Florencia
Teixidor, Francesc
Viñas, Clara
Planas, José Giner
Choquesillo Lazarte, Duane
Vanthuyne, Nicolas
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Molecular Chirality
Carborane
Supramolecular Chirality
topic Molecular Chirality
Carborane
Supramolecular Chirality
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Ten structurally related racemic 2-pyridylmethyl alcohols containing an o-carborane core (1,2-closo-C2B10H10; rac-1a) or m-carborane (1,7-closo-C2B10H10; rac-2a) or p-carborane (1,7-closo-C2B10H10; rac-3a) and their enantiopure forms (R- and S-1a or R- and S-2a or R- and S-3a), as well as an iodo derivative of rac-3a (rac-4a) and a non-carborane derivative (C6H5; rac-5) have been studied by single crystal X-ray crystallography. All racemic and enantiopure structures show O-H⋯N hydrogen bonded homochiral 21-helical networks, except that for rac-3a, which forms O-H⋯N hydrogen bonded trimers. A comparison of these X-ray structures with that for others found in the Cambridge Structural Database for chiral 2-pyridyl alcohols-either in racemic or enantiopure forms-that form O-H⋯N hydrogen bonded homochiral 21-helical networks reveals a possible relationship between the torsion angle of the hydrogen bond donor and acceptor groups in these molecules and the hydrogen bonded supramolecular helices formed in the solid state.
Fil: Tsang, Min Ying. Consejo Superior de Investigaciones Científicas. Instituto de Ciencia de Los Materiales de Barcelona; España
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: 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: Choquesillo Lazarte, Duane. Universidad de Granada; España. Consejo Superior de Investigaciones Científicas; España
Fil: Vanthuyne, Nicolas. Aix Marseille Universite; Francia
description Ten structurally related racemic 2-pyridylmethyl alcohols containing an o-carborane core (1,2-closo-C2B10H10; rac-1a) or m-carborane (1,7-closo-C2B10H10; rac-2a) or p-carborane (1,7-closo-C2B10H10; rac-3a) and their enantiopure forms (R- and S-1a or R- and S-2a or R- and S-3a), as well as an iodo derivative of rac-3a (rac-4a) and a non-carborane derivative (C6H5; rac-5) have been studied by single crystal X-ray crystallography. All racemic and enantiopure structures show O-H⋯N hydrogen bonded homochiral 21-helical networks, except that for rac-3a, which forms O-H⋯N hydrogen bonded trimers. A comparison of these X-ray structures with that for others found in the Cambridge Structural Database for chiral 2-pyridyl alcohols-either in racemic or enantiopure forms-that form O-H⋯N hydrogen bonded homochiral 21-helical networks reveals a possible relationship between the torsion angle of the hydrogen bond donor and acceptor groups in these molecules and the hydrogen bonded supramolecular helices formed in the solid state.
publishDate 2015
dc.date.none.fl_str_mv 2015-02
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/11336/37614
Tsang, Min Ying; Di Salvo, Florencia; Teixidor, Francesc; Viñas, Clara; Planas, José Giner; et al.; Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols; American Chemical Society; Crystal Growth & Design; 15; 2; 2-2015; 935-945
1528-7483
CONICET Digital
CONICET
url http://hdl.handle.net/11336/37614
identifier_str_mv Tsang, Min Ying; Di Salvo, Florencia; Teixidor, Francesc; Viñas, Clara; Planas, José Giner; et al.; Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols; American Chemical Society; Crystal Growth & Design; 15; 2; 2-2015; 935-945
1528-7483
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/cg501748x
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/cg501748x
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 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
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score 13.087074

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