title: Determining absolute configuration in flexible molecules: a case study.
abstract: 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.
authors.affiliation: Department of Chemistry, Princeton University, Princeton, NJ 08544, USA.
authors.forename: K M
authors.initials: KM
authors.lastname: Specht
authors.forename: J
authors.initials: J
authors.lastname: Nam
authors.forename: D M
authors.initials: DM
authors.lastname: Ho
authors.forename: N
authors.initials: N
authors.lastname: Berova
authors.forename: R K
authors.initials: RK
authors.lastname: Kondru
authors.forename: D N
authors.initials: DN
authors.lastname: Beratan
authors.forename: P
authors.initials: P
authors.lastname: Wipf
authors.forename: R A
authors.initials: RA
authors.lastname: Pascal
authors.forename: D
authors.initials: D
authors.lastname: Kahne
mesh_terms: 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
chemical_list: D001565:Benzoates; D009281:Naphthalenes; D012996:Solutions