Directly probing the racemization of imidazolines by vibrational circular dichroism: kinetics and mechanism.
The first report of monitoring the kinetics of racemization in solution by online vibrational circular dichroism (VCD), chemometrics, and density functional theory (DFT) calculations is presented. The activation energy for the racemization of an imidazoline based on the experimental VCD was determined, and the detailed mechanism of the process utilizing DFT calculations was elucidated. This study demonstrates the utility of VCD for the determination of reaction mechanisms in asymmetric transformations.
Ma
Shengli
S
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, Connecticut 06877, USA.
Busacca
Carl A
CA
Fandrick
Keith R
KR
Bartholomeyzik
Teresa
T
Haddad
Nizar
N
Shen
Sherry
S
Lee
Heewon
H
Saha
Anjan
A
Yee
Nathan
N
Senanayake
Chris
C
Grinberg
Nelu
N
D002942:Circular Dichroism / Q000379:methods*; D048288:Imidazolines / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D013237:Stereoisomerism
D048288:Imidazolines