Crystallization of an achiral cyclohexanone ethylene ketal in enantiomorphs and determination of the absolute structure.
The achiral 4-methoxy-4-(p-methoxyphenyl)-cyclohexanone ethylene ketal (1) resolves spontaneously. The crystal structure is solved in chiral spatial group P2(1). Because compound 1 is composed of only light atoms (C, H, O) it is not possible to determine its absolute structure configuration. An efficient procedure for the absolute structure configuration determination of flexible molecules containing only light atoms is proposed, based on the combination of X-ray diffraction, solid-state VCD, and DFT calculations.
Graus
Sara
S
Química Orgánica, Centro Politécnico Superior-Instituto de Nanociencia de Aragón, Universidad de Zaragoza, 50015 Zaragoza, Spain.
Tejedor
Rosa M
RM
Uriel
Santiago
S
Serrano
José Luis
JL
Alkorta
Ibon
I
Elguero
José
J
D000042:Absorption; D002942:Circular Dichroism; D003460:Crystallization; D003510:Cyclohexanes / Q000737:chemistry*; D003512:Cyclohexanones / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D003510:Cyclohexanes; D003512:Cyclohexanones; D004988:Ethers, Cyclic; C036468:cyclohexanone