Determining absolute configuration in flexible molecules: a case study.
Assigning absolute configuration of molecules continues to be a major problem. Determining absolute configuration in conformationally flexible systems is challenging, even for experts. Here, we present a case study in which we use a combination of molecular modeling, solution NMR, and X-ray crystallography to illustrate why it is difficult to use solution methods alone for configuration assignment. For the case examined, a comparison of calculated and experimental optical rotatory dispersion (ORD) data provides the most straightforward way to assign the absolute configuration.
Specht
K M
KM
Department of Chemistry, Princeton University, Princeton, NJ 08544, USA.
Nam
J
J
Ho
D M
DM
Berova
N
N
Kondru
R K
RK
Beratan
D N
DN
Wipf
P
P
Pascal
R A
RA
Kahne
D
D
D001565:Benzoates / Q000737:chemistry*; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry*; D009905:Optical Rotatory Dispersion / Q000379:methods*; D012996:Solutions; D013237:Stereoisomerism; D013816:Thermodynamics
D001565:Benzoates; D009281:Naphthalenes; D012996:Solutions