Calix[5]arenes: Molecular recognition of carboranes

ORGN 790

Thomas E. Clark, Mohamed Makha, Colin L. Raston, clraston@chem.uwa.edu.au, and Alexandre N. Sobolev. School of Biomedical, Biomolecular and Chemical Sciences, The University of Western Australia, 35 Stirling Highway, Crawley, Perth, 6009, Australia
p-But-calix[5]arene, 1, forms inclusion complexes with o- and m-carboranes, 2(a) and 2(b) respectively, in toluene or dichloromethane/hexane. A 1:1 host-guest supermolecule is formed in all cases with the carborane sitting snugly in the cavity forming two C-H...π interactions with the calixarene. The p-But-subsitutents orientate themselves in such a manner as to shroud the carborane and hold it deep within the cavity. The p-isomer, 2(c), does not form inclusion complexes in solvents capable of forming C-H...π interactions. However it forms an inclusion complex in solvents such as hexane. The effect on changing the p-But-group to either a p-H, p-Ph, or p-Bn, compounds, 3-5 respectively, will also be presented.

 

Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006