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J Am Chem Soc. 2011 Aug 24;133(33):12918-21. doi: 10.1021/ja203509s. Epub 2011 Jul 27.

Planar hydrocarbons more optically active than their isomeric helicenes.

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  • 1Department of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, USA.

Abstract

Comparisons are made of the calculated optical rotation tensors of C(2v)-symmetric, polyaromatic hydrocarbons and their [5]helicene, [6]helicene, and [7]helicene isomers. Seven ∩-shaped, planar compounds had, in each case, larger computed tensor elements than the chiral helicenes. Merely obviating the condition of solution averaging wholly changes expectations of the magnitudes and etiologies of optical activity. Symmetries of achiral compounds facilitate semiquantitative correlations between structure and optical rotation.

PMID:
21793486
DOI:
10.1021/ja203509s
[PubMed]
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