Abstract
The coupling of a student experiment involving the preparation and use of a catalyst for the asymmetric epoxidation of an alkene with computational simulations of various properties of the resulting epoxide is set out in the form of a software toolbox from which students select appropriate components. At the core of these are the computational spectroscopic tools, whereby a measured spectrum can be interpreted in some detail using theoretical simulations. These include a range of modern chiroptical methods to accompany the increased use of such techniques in modern teaching laboratories. Computational experiments are captured in a Wiki-based electronic laboratory notebook, which features data-stamping, authenticated entries, and inclusion of semantically intact data via interactive models rendered within the Wiki using JSmol and its referencing via a digital object identifier (DOI) to a digital data repository.
Highlights
Organic syntheses are increasingly dependent on computational simulations to provide insight into the reactions being conducted in the laboratory
All of these concepts can be juxtaposed upon a well-defined existing experimental procedure to provide a student experiment where both the practical and the computational modeling can be carried out, and for which the whole would be greater than the sum of the parts
Optical rotatory power (ORP) at one or more wavelengths was first seminally applied by Kirkwood in 195212 to verify the correctness of Fischer’s original guess for the absolute configuration of glyceraldehyde. Students discovered that their computed rotation may be quite variable because even such simple alkene epoxides can have several different conformations involving the phenyl group, and optical rotations can be highly sensitive to conformation.[13]
Summary
Organic syntheses are increasingly dependent on computational simulations to provide insight into the reactions being conducted in the laboratory. Students are introduced to the procedures for quantum mechanical prediction of IR, NMR, and chiroptical properties for a real molecule, a task that requires comparing these values with experimentally measured counterparts.
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