Regular Article/Proceedings of the 19th International Symposium on Chirality (ISCD-19), San Diego

Chiral molecules with polyhedral T, O, or I symmetry: Theoretical solution to a difficult problem in stereochemistry

  1. Sri Kamesh Narasimhan1,
  2. Xiaoying Lu1,
  3. Yan-Yeung Luk1,2,*

Article first published online: 11 FEB 2008

DOI: 10.1002/chir.20545

Issue

Chirality

Chirality

Special Issue: Proceedings of the 19th International Symposium on Chirality (ISCD-19), San Diego

Volume 20, Issue 8, pages 878–884, August 2008

Additional Information

How to Cite

Narasimhan, S. K., Lu, X. and Luk, Y.-Y. (2008), Chiral molecules with polyhedral T, O, or I symmetry: Theoretical solution to a difficult problem in stereochemistry. Chirality, 20: 878–884. doi: 10.1002/chir.20545

Author Information

  1. 1

    Department of Chemistry, Syracuse University, Syracuse, New York

  2. 2

    Department of Biomedical and Chemical Engineering, Syracuse University, Syracuse, New York

*Department of Chemistry, Department of Biomedical and Chemical Engineering, Syracuse University 1-014 CST, 111 College Place, Syracuse, NY 13244

Publication History

  1. Issue published online: 8 JUL 2008
  2. Article first published online: 11 FEB 2008
  3. Manuscript Accepted: 5 JAN 2008
  4. Manuscript Received: 5 SEP 2007

Funded by

  • Syracuse University
  • Stereochemical Society of Greater New York (Administrated at Columbia University, NY)
  • Syracuse Center of Excellence CARTI award funded by U.S. Environmental Protection Agency. Grant Number: X-8323501-0
  • National Science Foundation-CMMI. Grant Number: 0727491

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Keywords:

  • chiral polyhedral symmetry;
  • dissymmetry;
  • stereochemistry;
  • trioxatricornan;
  • T, O, I symmetry

Abstract

Ever since point groups of symmetry have been used to describe molecules after Van't Hoff and Le Bel proposed tetrahedral structures for carbon atoms in 1874, it remains difficult to design chiral molecules with polyhedral symmetry T, O, or I. Past theoretical and experimental studies have mainly accomplished molecular structures that have the conformations for satisfying the T symmetry. In this work, we present a general theoretical approach to construct rigid molecular structures that have permanently the symmetry of T, O, and I. This approach involves desymmetrizaton of the vertices or the edges of Platonic solid-shaped molecules with dissymmetric moieties. Using density functional theory (DFT) and assisted model building and energy refinement (AMBER) computational methods, the structure, the rigidity, and the symmetry of the molecule are confirmed by assessing the lowest energy conformation of the molecule, which is initially presented in a planar graph. This method successfully builds molecular structures that have the symmetry of T, O, and I. Interestingly, desymmetrization of the edges has a more stringent requirement of rigidity than desymmetrization of the vertices for affording the T, O, or I symmetry. Chirality, 2008. © 2008 Wiley-Liss, Inc.

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