A facile method to determine the absolute structure of achiral molecules: Supramolecular-tilt structures
| Autor: | Sara Graus, Santiago Uriel, Rosa M. Tejedor, Concepción López, Ibon Alkorta, José Luis Serrano, José Elguero, Marta Pérez-Torralba, Rosa M. Claramunt, Teresa Sierra |
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| Přispěvatelé: | Comunidad de Madrid, Gobierno de Aragón, Comisión Interministerial de Ciencia y Tecnología, CICYT (España) |
| Rok vydání: | 2013 |
| Předmět: |
Enantiomeric excess
Noncovalent interactions Stereochemistry Supramolecular chemistry Pyrazole Catalysis chemistry.chemical_compound Non-covalent interactions Molecule Chirality chemistry.chemical_classification Molecular Structure Cyclohexanones Circular Dichroism Organic Chemistry Stereoisomerism General Chemistry X-ray diffraction Crystallography Vibrational circular dichroism chemistry X-ray crystallography Pyrazoles Chirality (chemistry) |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname |
| Popis: | Achiral compounds 4-methoxy-4-(p-methoxyphenyl)cyclohexanoneethylene ketal (2), 4-hydroxy-4-(p-methoxy phenyl)cyclohexanoneethylene ketal (3), and 3,5-dimethyl-4-nitropyrazole (4) crystallized in chiral structures and the samples showed an enantiomeric excess. We have determined the absolute structures of these compounds by using X-ray diffraction with copper radiation at low temperatures. Moreover, we have also established the prevalent absolute structures in these samples, by comparing their calculated and solid-state vibrational circular dichroism (VCD) spectra. The consistency of this method was confirmed by using (R,R)-2,8-diiodo-4,10-dimethyl-6 H,12H-5,11-methano- dibenzo[b,f][1,5]diazocine, Tröger′s base, (R,R)-1, as a chiral compound of known absolute configuration. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. The authors are grateful to the CICYT FEDER Spanish Project (MAT2009-1463-C03-01, MAT2011-27978-C02-01, and CTQ2010-16122) and to the Governments of Aragón and Madrid (Project MADRISOLAR2, reference S2009/PPQ-1533) for funding. |
| Databáze: | OpenAIRE |
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