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Racemization Barriers of Helicenes:  A Computational Study1

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Contribution from the Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, D-48149 Münster, Germany, and CAOS/CAMM Center, University of Nijmegen, P.O. Box 9060, 6500 GL Nijmegen, The Netherlands
Cite this: J. Am. Chem. Soc. 1996, 118, 25, 6031–6035
Publication Date (Web):June 26, 1996
https://doi.org/10.1021/ja950774t
Copyright © 1996 American Chemical Society
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Abstract

The racemization barriers of pentahelicene up to nonahelicene have been computed with AM1, MNDO, and PM3. All methods lead to Cs transition states which have lower energy than those with C2v symmetry. The barriers calculated by AM1 match the experimental values best for all helicenes. The reliability of the results has been confirmed by ab initio methods using the B3LYP functional with the 3-21G basis set as implemented in the GAUSSIAN94 package. Furthermore, 12 methyl-substituted helicenes have been computed with the AM1 method. The racemization barriers of 1-methyl-substituted penta- and hexahelicene are at least as high as that of the next higher unsubstituted helicene. A second methyl group in the 1‘-position increases the barrier further, while methyl groups in the 2-position do not have a severe influence on the racemization barrier.

†

 Organisch-Chemisches Institut.

*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

‡

 University of Nijmegen.

✗

 Abstract published in Advance ACS Abstracts, June 1, 1996.

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