Determination of the Dimerization Equilibrium Constants of Omeprazole and Pirkle's Alcohol through Optical-Rotation Measurements
METADATA ONLY
Loading...
Author / Producer
Date
2004-08
Publication Type
Journal Article
ETH Bibliography
yes
Citations
Altmetric
METADATA ONLY
Data
Rights / License
Abstract
A new procedure to measure the equilibrium constants for the dimerization (homochiral and heterochiral) reactions of enantiomers in solution was applied to two different compounds, namely omeprazole and Pirkle's alcohol, both in CHCl3. This procedure is based on the measurement of the optical rotation of the solution as a function of its composition, which exhibits a nonlinear dependence on the enantiomer enrichment. Such nonlinearity depends on the extent of dimerization, and it is a strong effect in the case of omeprazole, whose equilibrium constants are 14.0±3.5 l/mol and 25.2±4.0 l/mol for the formation of homochiral and of heterochiral dimers, respectively. Pirkle's alcohol exhibits a weaker effect that allows only to estimate the order of magnitude of these constants, i.e., ca. 0.10 and 0.34 l/mol, respectively.
Permanent link
Publication status
published
External links
Editor
Book title
Journal / series
Volume
87 (8)
Pages / Article No.
1917 - 1926
Publisher
Wiley‐VHCA
Event
Edition / version
Methods
Software
Geographic location
Date collected
Date created
Subject
Organisational unit
03484 - Mazzotti, Marco (emeritus) / Mazzotti, Marco (emeritus)