English   español  
Por favor, use este identificador para citar o enlazar a este item: http://hdl.handle.net/10261/18781
Compartir / Impacto:
Estadísticas
Add this article to your Mendeley library MendeleyBASE
Citado 14 veces en Web of Knowledge®  |  Pub MebCentral Ver citas en PubMed Central  |  Ver citas en Google académico
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Título

Chiral symmetry breaking and polymorphism in 1,1’-binaphthyl melt crystallization.

AutorSainz-Díaz, C. Ignacio; Martín-Islán, Africa P.; Cartwright, Julyan H. E.
Fecha de publicación20-sep-2005
EditorAmerican Chemical Society
CitaciónJ. Phys. Chem. B. 109(40): 18758-18764 (2005)
ResumenWe have studied chiral symmetry breaking in the melt crystallization of 1,1‘-binaphthyl. We confirm that chiral symmetry breaking can be induced by stirring the melt as it crystallizes. We find an additional process of vapor crystallization to occur alongside the melt crystallization. This complicates the analysis of the enantiomorphism by introducing a further phenomenon: that of polymorphism. Crystallographic studies by X-ray diffraction reveal two polymorphs of 1,1‘-binaphthyl that are made up of two different conformers of each of the two enantiomeric forms of the molecule. Crystals from the melt are generally chiral tetragonal crystals (P42121) composed of (R)- or (S)-1,1‘-binaphthyl in a transoid conformer, while those from the vapor are racemic monoclinic crystals (C2/c) made up of the cisoid conformer of both (R)- and (S)-1,1‘-binaphthyl enantiomers. The main intermolecular interactions in all these crystals are weak aromatic CH/π hydrogen bonds, which are responsible for the enantiomeric discrimination in the molecular recognition during crystallization. A tendency for whisker crystal formation is notable in 1,1‘-binaphthyl. In stirred crystallization, fluid and mechanical forces can break off these whiskers, which provide secondary nuclei for further crystallization. This autocatalytic mechanism induces chiral symmetry breaking during the crystallization.
Descripción7 pages, 6 figures.
Versión del editorhttp://dx.doi.org/10.1021/jp0518198
URIhttp://hdl.handle.net/10261/18781
DOI10.1021/jp0518198
Aparece en las colecciones: (IACT) Artículos
Ficheros en este ítem:
No hay ficheros asociados a este ítem.
Mostrar el registro completo
 



NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.