A general method to predict optical rotations of chiral molecules from their structures

The relationship of the chiroptical response of a molecule to its absolution configuration does not exist now. In this letter, I intend to report a general rule with exceptions to predict the sign of optical rotation of chiral molecules with a RCHXY structure from their absolute configurations using...

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Bibliographic Details
Published in:RSC advances 2023-01, Vol.13 (7), p.4775-478
Main Author: Ji, Hai-Feng
Format: Article
Language:English
Subjects:
Chemistry
Configurations
Functional groups
Molecular structure
Optical properties
Optical rotation
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Summary:The relationship of the chiroptical response of a molecule to its absolution configuration does not exist now. In this letter, I intend to report a general rule with exceptions to predict the sign of optical rotation of chiral molecules with a RCHXY structure from their absolute configurations using the Hammett constant, σ p , which is based on the electron withdrawing/donating power of functional groups. In this rule, a priority list of functional groups based on the electron withdrawing powers of the groups are used. When the lowest priority group is in the back of the molecule, a clockwise arrangement of the other three priorities from the most electron withdrawing to the least withdrawing (1-2-3) is predicted to be dextrorotatory, the counterclockwise arrangement is predicted to be levorotatory. The relationship of the chiroptical response of a molecule to its absolution configuration does not exist now.
ISSN:2046-2069
2046-2069
DOI:10.1039/d2ra08290j