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Determination of absolute configuration using optical rotation calculated using density functional theory.

P J Stephens¹, F J Devlin, J R Cheeseman

¹Department of Chemistry, University of Southern California, Los Angeles, California 90089-0482, USA. pstephen@usc.edu

Organic Letters

|December 20, 2002

Summary

This study introduces a novel method for determining the absolute configurations (ACs) of chiral molecules. It utilizes calculated optical rotations from density functional theory (DFT), offering a new computational approach for chemical structure elucidation.

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Area of Science:

Computational Chemistry
Organic Chemistry
Spectroscopy

Background:

Determining the absolute configuration (AC) of chiral molecules is crucial in stereochemistry.
Traditional methods can be resource-intensive or provide limited information.

Purpose of the Study:

To establish a computational method for determining the ACs of chiral molecules.
To validate the use of calculated optical rotations via density functional theory (DFT).

Main Methods:

Calculated specific rotations using time-dependent DFT/gauge-invariant atomic orbital (TDDFT/GIAO) methodology.
Employed the B3LYP functional with the aug-cc-pVDZ basis set.
Compared calculated values to experimental data for validation.

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Main Results:

Successfully determined the ACs for three novel chiral molecules: 2H-naphtho[1,8-bc]thiophene 1-oxide (3), naphtho[1,8-cd]-1,2-dithiole 1-oxide (4), and 9-phenanthryl methyl sulfoxide (5).
Demonstrated the efficacy of DFT-calculated optical rotations in AC determination.

Conclusions:

The study presents the first reported use of DFT-calculated optical rotations for determining absolute configurations.
This computational approach offers a viable and efficient alternative for stereochemical analysis.