What is the π electron size limit for neutral bishomoaromaticity?: a DFT study

ORGN 943

Philip M. Warner, p.warner@neu.edu, Department of Chemistry, Northeastern University, Boston, MA 02115
In 2004, a paper (JACS 2004, 126, 4256) reported DFT calculations on a series of extended barbaralanes containing up to 18 pi electrons. These molecules were calculated to be non-classical, but due to geometric constraints, cross-ring interactions were thought to contribute to their stabilization. Thus these were characterized as bishomoaromatic sigma-polyacenes. We now report a similar study of systems that do not have cross-ring interactions, and are thus only "annulenic" in nature. We will discuss the size limits for bishomoaromaticity in such systems.

 

Heterocycles and Aromatics
8:00 AM-12:00 PM, Thursday, August 23, 2007 BCEC -- 254 A/B, Oral

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007