A facile method to determine the absolute structure of achiral molecules: Supramolecular-tilt structures

Tejedor, R.M. (Universidad de Zaragoza) ; Uriel, S. (Universidad de Zaragoza) ; Graus, S. (Universidad de Zaragoza) ; Sierra, T. (Universidad de Zaragoza) ; Serrano, J.L. (Universidad de Zaragoza) ; Claramunt, R.M. ; López, C. ; Pérez-Torralba, M. ; Alkorta, I. ; Elguero, J.

Resumen: 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.

Idioma: Inglés

DOI: 10.1002/chem.201204197

Año: 2013

Publicado en: Chemistry - A European Journal 19, 19 (2013), 6044-6051
ISSN: 0947-6539

Factor impacto JCR: 5.696 (2013)

Categ. JCR: CHEMISTRY, MULTIDISCIPLINARY rank: 22 / 145 = 0.152 (2013) - Q1 - T1

Financiación: info:eu-repo/grantAgreement/ES/CICYT/CTQ2010-16122
Financiación: info:eu-repo/grantAgreement/ES/CICYT/MAT2009-1463-C03-01
Financiación: info:eu-repo/grantAgreement/ES/CICYT/MAT2011-27978-C02-01

Tipo y forma: Artículo (PostPrint)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)
Área (Departamento): Área Laboratorios F. Ciencias (Dpto. Química Física)