Synfacts 2010(7): 0767-0767  
DOI: 10.1055/s-0029-1220066
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Substituent Effect on Molecular Shape of a Macrotricyclic Receptor

Contributor(s): Timothy M. Swager, Joel Batson
A. Lélias-Vanderperre, E. Aubert, J.-C. Chambron*, E. Espinosa*
Université de Bourgogne, Dijon and Nancy Université, France
Further Information

Publication History

Publication Date:
22 June 2010 (online)

Significance

In an investigation into the effect of substituents on molecular shape, the authors extend the family of C 3v -symmetric macrotricycles from 9,10 to include 7 and 8. Whereas 7 displays a spherical tetrahedral shape, 8 takes up an elongated/cylindrical tetrahedral shape. Surprisingly, bulky heteroatomic substitution at the lower position of the ‘walls’ by Br (7) and MeS (8) result in the same shape as persubstitution of the mesitylene-derived ‘cap’ 8.