Electronic and steric effects in binding of deep cavitands.
A deep, self-folding cavitand responds to minor electronic differences between suitably sized adamantane guests. Binding constants range from <0.5 to 4000 M(-1) for guests as similar as 1-bromoadamantane and 1-cyanoadamantane. The barriers to guest exchange also vary up to 3 kcal mol(-1).
Hooley
Richard J
RJ
Department of Chemistry, The Scripps Research Institute MB-26, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Shenoy
Siddhartha R
SR
Rebek
Julius
J
D000218:Adamantane / Q000737:chemistry; D004583:Electrons; D004988:Ethers, Cyclic / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D012118:Resorcinols / Q000737:chemistry*
D004988:Ethers, Cyclic; D012118:Resorcinols; C442939:cavitand; D000218:Adamantane