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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/7974
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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 Técnicas2025-09-29T10:18:43Zoai: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:34982025-09-29 10:18:43.3CONICET 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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1844614152280080384 |
score |
13.070432 |