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Supramolecular crystalline construction based on a mandelic acid source. Host design, inclusion formation and X-ray crystal structures of a methanol inclusion complex and free host structures in racemic and optically resolved forms

1996; Wiley; Volume: 9; Issue: 1 Linguagem: Inglês

10.1002/(sici)1099-1395(199601)9

1099-1395

Edwin Weber, Orm Hager, Concepción Foces‐Foces, A.L. Llamas-Saiz,

Molecular spectroscopy and chirality

Journal of Physical Organic ChemistryVolume 9, Issue 1 p. 50-60 Research Article Supramolecular crystalline construction based on a mandelic acid source. Host design, inclusion formation and X-ray crystal structures of a methanol inclusion complex and free host structures in racemic and optically resolved forms Edwin Weber, Corresponding Author Edwin Weber Institut für Organische Chemie der Technischen Universität Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, GermanyInstitut für Organische Chemie der Technischen Universität Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany===Search for more papers by this authorOrm Hager, Orm Hager Institut für Organische Chemie der Technischen Universität Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, GermanySearch for more papers by this authorConcepcion Foces-Foces, Concepcion Foces-Foces Departamento de Cristalografia, Instituto de Quimica-Fisica 'Rocasolano,' CSIC, Serrano 119, E-28006 Madrid, SpainSearch for more papers by this authorAntonio L. Llamas-Saiz, Antonio L. Llamas-Saiz Departamento de Cristalografia, Instituto de Quimica-Fisica 'Rocasolano,' CSIC, Serrano 119, E-28006 Madrid, SpainSearch for more papers by this author Edwin Weber, Corresponding Author Edwin Weber Institut für Organische Chemie der Technischen Universität Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, GermanyInstitut für Organische Chemie der Technischen Universität Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany===Search for more papers by this authorOrm Hager, Orm Hager Institut für Organische Chemie der Technischen Universität Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, GermanySearch for more papers by this authorConcepcion Foces-Foces, Concepcion Foces-Foces Departamento de Cristalografia, Instituto de Quimica-Fisica 'Rocasolano,' CSIC, Serrano 119, E-28006 Madrid, SpainSearch for more papers by this authorAntonio L. Llamas-Saiz, Antonio L. Llamas-Saiz Departamento de Cristalografia, Instituto de Quimica-Fisica 'Rocasolano,' CSIC, Serrano 119, E-28006 Madrid, SpainSearch for more papers by this author First published: January 1996 https://doi.org/10.1002/(SICI)1099-1395(199601)9:1 3.0.CO;2-4Citations: 6AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract A new host compound in optically resolved and racemic forms for selective crystalline inclusion formation derived from natural mandelic acid was synthesized. Inclusion properties of the two optical species are discussed, involving comparison with a lactic acid-based host analogue. Inclusion compounds with amines, ketones and heterocyclics and specifically with small unbranched alcohols were isolated. The crystal and molecular structures of the optically resolved and racemic forms of the free host at room temperature and the methanol inclusion complex of the resolved host at 255 K were determined by x-ray analysis. Two different binding schemes characterize the packing of these structures, in which one hydroxyl group is responsible for the formation of dimers and chains while in the free host the other hydroxyl group is involved in OH···phenyl interactions. A survey of the OH ···phenyl interactions based on the Cambridge Structural Data Base (October 1994 version) reveals that π-electron bonding occurs in a wide range of crystal structures. The approximation of the hydrogen appears to take place in an asymmetric way. Several calculations for the ab initio prediction of the crystal structures were performed. Citing Literature Volume9, Issue1January 1996Pages 50-60 RelatedInformation