Electronic and Steric Effects in Binding of Deep Cavitands

被引:29
作者
Hooley, Richard J.
Shenoy, Siddhartha R.
Rebek, Julius, Jr. [1 ]
机构
[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1021/ol8022775
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
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).
引用
收藏
页码:5397 / 5400
页数:4
相关论文
共 35 条
[1]
Anslyn E.V., 2006, MODERN PHYS ORGANIC, P367
[2]
Molecular recognition of protein-ligand complexes: Applications to drug design [J].
Babine, RE ;
Bender, SL .
CHEMICAL REVIEWS, 1997, 97 (05) :1359-1472
[3]
A synthetic mimic of protein inner space: Buried polar interactions in a deep water-soluble host [J].
Butterfield, Sara M. ;
Rebek, Julius, Jr. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (48) :15366-15367
[4]
Supramolecular catalysis of a unimolecular transformation: Aza-cope rearrangement within a self-assembled host [J].
Fiedler, D ;
Bergman, RG ;
Raymond, KN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (48) :6748-6751
[5]
Molecular paneling via coordination [J].
Fujita, M ;
Umemoto, K ;
Yoshizawa, M ;
Fujita, N ;
Kusukawa, T ;
Biradha, K .
CHEMICAL COMMUNICATIONS, 2001, (06) :509-518
[6]
Templated assembly of water-soluble nano-capsules: Inter-phase sequestration, storage, and separation of hydrocarbon gases [J].
Gibb, Corinne L. D. ;
Gibb, Bruce C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (51) :16498-16499
[7]
Container molecules with portals: Reversibly switchable cycloalkane complexation [J].
Gottschalk, Thomas ;
Jaun, Bernhard ;
Diederich, Francois .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (1-2) :260-264
[8]
Pairwise selection of guests in a cylindrical molecular capsule of nanometre dimensions [J].
Heinz, T ;
Rudkevich, DM ;
Rebek, J .
NATURE, 1998, 394 (6695) :764-766
[9]
Hof F, 2002, ANGEW CHEM INT EDIT, V41, P1488, DOI 10.1002/1521-3773(20020503)41:9<1488::AID-ANIE1488>3.0.CO
[10]
2-G