Synthesis and Crystallographic Studies of Disubstituted Carboranyl Alcohol Derivatives: Prevailing Chiral Recognition?

Autores
Di Salvo, Florencia; Paterakis, Christos; Ying Tsang, Min; García, Yolanda; Viñas, Clara; Teixidor, Francesc; Giner Planas, José; Light, Mark E.; Hursthouse, Michael B.; Choquesillo Lazarte, Duane
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The syntheses of new o-carboranyldiols bearing aromatic rings bis-[R(hydroxy)methyl]-1,2-dicarba-closo-dodecaborane (R = 2-pyridyl 1a, 3-pyridyl 1b, 4-pyridyl 1c, 2-quinolyl 1d, 4-quinolyl 1e, henyl 1f) are reported. The compounds are obtained as mixtures of meso (syn) and racemic (anti) stereoisomers with a slight diastereomeric excess (syn:anti ratio of 0.7:1) in all cases but in 1b. The cristal structures of the meso compounds syn-1a.2MeOH, syn-1b, syn-1f.0.25H2 O and racemic anti-1a.MeOH, anti-1a.EtOH, and anti-1d.2H2 O are reported. We provide an analysis of these compounds by means of NMR and X-ray crystallography, in the context of crystal engineering and chiral recognition. The results show that the cristal packings for these alcohols are dominated by the supramolecular O-H...N and/or O-H...O hydrogen bonds. Supramolecular analysis of all compounds in this work reveals that homochiral self-assembly, that is, formation of homochiral hydrogen bonded complexes, prevails over heterochiral self-assembly (formation of heterochiral hydrogen bonded complexes).
Fil: Di Salvo, Florencia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; España
Fil: Paterakis, Christos . Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; España
Fil: Ying Tsang, Min . Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; España
Fil: García, Yolanda. Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; España
Fil: Viñas, Clara . Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; España
Fil: Teixidor, Francesc . Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; España
Fil: Giner Planas, José . Consejo Superior de Investigaciones Cientificas. 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
Fil: Choquesillo Lazarte, Duane . Consejo Superior de Investigaciones Cientificas; España
Materia
Chiral Recognition
Crystal Engineering
Boron Clusters
Diols
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:11336/7974
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/7974
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and Crystallographic Studies of Disubstituted Carboranyl Alcohol Derivatives: Prevailing Chiral Recognition?Di Salvo, FlorenciaPaterakis, Christos Ying Tsang, Min García, YolandaViñas, Clara Teixidor, Francesc Giner Planas, José Light, Mark E. Hursthouse, Michael B. Choquesillo Lazarte, Duane Chiral RecognitionCrystal EngineeringBoron ClustersDiolshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The syntheses of new o-carboranyldiols bearing aromatic rings bis-[R(hydroxy)methyl]-1,2-dicarba-closo-dodecaborane (R = 2-pyridyl 1a, 3-pyridyl 1b, 4-pyridyl 1c, 2-quinolyl 1d, 4-quinolyl 1e, henyl 1f) are reported. The compounds are obtained as mixtures of meso (syn) and racemic (anti) stereoisomers with a slight diastereomeric excess (syn:anti ratio of 0.7:1) in all cases but in 1b. The cristal structures of the meso compounds syn-1a.2MeOH, syn-1b, syn-1f.0.25H2 O and racemic anti-1a.MeOH, anti-1a.EtOH, and anti-1d.2H2 O are reported. We provide an analysis of these compounds by means of NMR and X-ray crystallography, in the context of crystal engineering and chiral recognition. The results show that the cristal packings for these alcohols are dominated by the supramolecular O-H...N and/or O-H...O hydrogen bonds. Supramolecular analysis of all compounds in this work reveals that homochiral self-assembly, that is, formation of homochiral hydrogen bonded complexes, prevails over heterochiral self-assembly (formation of heterochiral hydrogen bonded complexes).Fil: Di Salvo, Florencia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; EspañaFil: Paterakis, Christos . Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; EspañaFil: Ying Tsang, Min . Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; EspañaFil: García, Yolanda. Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; EspañaFil: Viñas, Clara . Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; EspañaFil: Teixidor, Francesc . Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; EspañaFil: Giner Planas, José . Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; EspañaFil: Light, Mark E. . University Of Southampton; Reino UnidoFil: Hursthouse, Michael B. . University Of Southampton; Reino UnidoFil: Choquesillo Lazarte, Duane . Consejo Superior de Investigaciones Cientificas; EspañaAmerican Chemical Society2013-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/7974Di Salvo, Florencia; Paterakis, Christos ; Ying Tsang, Min ; García, Yolanda; Viñas, Clara ; et al.; Synthesis and Crystallographic Studies of Disubstituted Carboranyl Alcohol Derivatives: Prevailing Chiral Recognition?; American Chemical Society; Crystal Growth & Design; 13; 4; 2-2013; 1473-14841528-7483enginfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/pdf/10.1021/cg400082zinfo:eu-repo/semantics/altIdentifier/url/http://dx.doi.org/10.1021/cg400082zinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-29T12:23:24Zoai:ri.conicet.gov.ar:11336/7974instacron: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:34982025-10-29 12:23:24.728CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and Crystallographic Studies of Disubstituted Carboranyl Alcohol Derivatives: Prevailing Chiral Recognition?
title Synthesis and Crystallographic Studies of Disubstituted Carboranyl Alcohol Derivatives: Prevailing Chiral Recognition?
spellingShingle Synthesis and Crystallographic Studies of Disubstituted Carboranyl Alcohol Derivatives: Prevailing Chiral Recognition?
Di Salvo, Florencia
Chiral Recognition
Crystal Engineering
Boron Clusters
Diols
title_short Synthesis and Crystallographic Studies of Disubstituted Carboranyl Alcohol Derivatives: Prevailing Chiral Recognition?
title_full Synthesis and Crystallographic Studies of Disubstituted Carboranyl Alcohol Derivatives: Prevailing Chiral Recognition?
title_fullStr Synthesis and Crystallographic Studies of Disubstituted Carboranyl Alcohol Derivatives: Prevailing Chiral Recognition?
title_full_unstemmed Synthesis and Crystallographic Studies of Disubstituted Carboranyl Alcohol Derivatives: Prevailing Chiral Recognition?
title_sort Synthesis and Crystallographic Studies of Disubstituted Carboranyl Alcohol Derivatives: Prevailing Chiral Recognition?
dc.creator.none.fl_str_mv Di Salvo, Florencia
Paterakis, Christos
Ying Tsang, Min
García, Yolanda
Viñas, Clara
Teixidor, Francesc
Giner Planas, José
Light, Mark E.
Hursthouse, Michael B.
Choquesillo Lazarte, Duane
author Di Salvo, Florencia
author_facet Di Salvo, Florencia
Paterakis, Christos
Ying Tsang, Min
García, Yolanda
Viñas, Clara
Teixidor, Francesc
Giner Planas, José
Light, Mark E.
Hursthouse, Michael B.
Choquesillo Lazarte, Duane
author_role author
author2 Paterakis, Christos
Ying Tsang, Min
García, Yolanda
Viñas, Clara
Teixidor, Francesc
Giner Planas, José
Light, Mark E.
Hursthouse, Michael B.
Choquesillo Lazarte, Duane
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Chiral Recognition
Crystal Engineering
Boron Clusters
Diols
topic Chiral Recognition
Crystal Engineering
Boron Clusters
Diols
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-carboranyldiols bearing aromatic rings bis-[R(hydroxy)methyl]-1,2-dicarba-closo-dodecaborane (R = 2-pyridyl 1a, 3-pyridyl 1b, 4-pyridyl 1c, 2-quinolyl 1d, 4-quinolyl 1e, henyl 1f) are reported. The compounds are obtained as mixtures of meso (syn) and racemic (anti) stereoisomers with a slight diastereomeric excess (syn:anti ratio of 0.7:1) in all cases but in 1b. The cristal structures of the meso compounds syn-1a.2MeOH, syn-1b, syn-1f.0.25H2 O and racemic anti-1a.MeOH, anti-1a.EtOH, and anti-1d.2H2 O are reported. We provide an analysis of these compounds by means of NMR and X-ray crystallography, in the context of crystal engineering and chiral recognition. The results show that the cristal packings for these alcohols are dominated by the supramolecular O-H...N and/or O-H...O hydrogen bonds. Supramolecular analysis of all compounds in this work reveals that homochiral self-assembly, that is, formation of homochiral hydrogen bonded complexes, prevails over heterochiral self-assembly (formation of heterochiral hydrogen bonded complexes).
Fil: Di Salvo, Florencia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; España
Fil: Paterakis, Christos . Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; España
Fil: Ying Tsang, Min . Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; España
Fil: García, Yolanda. Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; España
Fil: Viñas, Clara . Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; España
Fil: Teixidor, Francesc . Consejo Superior de Investigaciones Cientificas. Instituto de Ciencia de Los Materiales de Barcelona; España
Fil: Giner Planas, José . Consejo Superior de Investigaciones Cientificas. 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
Fil: Choquesillo Lazarte, Duane . Consejo Superior de Investigaciones Cientificas; España
description The syntheses of new o-carboranyldiols bearing aromatic rings bis-[R(hydroxy)methyl]-1,2-dicarba-closo-dodecaborane (R = 2-pyridyl 1a, 3-pyridyl 1b, 4-pyridyl 1c, 2-quinolyl 1d, 4-quinolyl 1e, henyl 1f) are reported. The compounds are obtained as mixtures of meso (syn) and racemic (anti) stereoisomers with a slight diastereomeric excess (syn:anti ratio of 0.7:1) in all cases but in 1b. The cristal structures of the meso compounds syn-1a.2MeOH, syn-1b, syn-1f.0.25H2 O and racemic anti-1a.MeOH, anti-1a.EtOH, and anti-1d.2H2 O are reported. We provide an analysis of these compounds by means of NMR and X-ray crystallography, in the context of crystal engineering and chiral recognition. The results show that the cristal packings for these alcohols are dominated by the supramolecular O-H...N and/or O-H...O hydrogen bonds. Supramolecular analysis of all compounds in this work reveals that homochiral self-assembly, that is, formation of homochiral hydrogen bonded complexes, prevails over heterochiral self-assembly (formation of heterochiral hydrogen bonded complexes).
publishDate 2013
dc.date.none.fl_str_mv 2013-02
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/11336/7974
Di Salvo, Florencia; Paterakis, Christos ; Ying Tsang, Min ; García, Yolanda; Viñas, Clara ; et al.; Synthesis and Crystallographic Studies of Disubstituted Carboranyl Alcohol Derivatives: Prevailing Chiral Recognition?; American Chemical Society; Crystal Growth & Design; 13; 4; 2-2013; 1473-1484
1528-7483
url http://hdl.handle.net/11336/7974
identifier_str_mv Di Salvo, Florencia; Paterakis, Christos ; Ying Tsang, Min ; García, Yolanda; Viñas, Clara ; et al.; Synthesis and Crystallographic Studies of Disubstituted Carboranyl Alcohol Derivatives: Prevailing Chiral Recognition?; American Chemical Society; Crystal Growth & Design; 13; 4; 2-2013; 1473-1484
1528-7483
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/pdf/10.1021/cg400082z
info:eu-repo/semantics/altIdentifier/url/http://dx.doi.org/10.1021/cg400082z
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 12.589754

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