Templation in the formation of carceplexes

被引:35
作者
Chapman, RG [1 ]
Sherman, JC [1 ]
机构
[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada
关键词
D O I
10.1021/jo9803582
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The formation of carceplexes and hemicarceplexes involves an assembly process whereby a molecular template is entrapped between two bowl-shaped molecules. The process can be highly selective such that a million-fold range in template recognition has been realized. The relative template abilities, or template ratios, for 34 molecules in forming carceplex a guest is described. Species with one, two, and three bridges linking the two "bowls" are reported and were used to delineate the guest-determining step of the reaction. The effect of base and solvent on the reaction are also described, and a discussion of the reaction mechanism is presented.
引用
收藏
页码:4103 / 4110
页数:8
相关论文
共 20 条
[1]  
CAREY FA, 1990, ADV ORG CHEM, P120
[2]  
Chapman R., UNPUB
[3]   Templation and encapsulation in supramolecular chemistry [J].
Chapman, RG ;
Sherman, JC .
TETRAHEDRON, 1997, 53 (47) :15911-15945
[4]   STUDY OF TEMPLATION AND MOLECULAR ENCAPSULATION USING HIGHLY STABLE AND GUEST-SELECTIVE SELF-ASSEMBLING STRUCTURES [J].
CHAPMAN, RG ;
SHERMAN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) :9081-9082
[5]   CARCEPLEX FORMATION - SCOPE OF A REMARKABLY EFFICIENT ENCAPSULATION REACTION [J].
CHAPMAN, RG ;
CHOPRA, N ;
COCHIEN, ED ;
SHERMAN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (01) :369-370
[6]   TEMPLATION EFFECTS ON FORMATION OF A HEMICARCEPLEX [J].
CHOPRA, N ;
SHERMAN, JC .
SUPRAMOLECULAR CHEMISTRY, 1995, 5 (01) :31-37
[7]   SHELL CLOSURE OF 2 CAVITANDS FORMS CARCERAND COMPLEXES WITH COMPONENTS OF THE MEDIUM AS PERMANENT GUESTS [J].
CRAM, DJ ;
KARBACH, S ;
KIM, YH ;
BACZYNSKYJ, L ;
KALLEYMEYN, GW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (08) :2575-2576
[8]  
CRAM DJ, 1994, SERIES MONOGRAPHS SU
[9]   AN ASYMMETRIC CARCEPLEX AND NEW CRYSTAL-STRUCTURE YIELD INFORMATION REGARDING A 1-MILLION-FOLD TEMPLATE EFFECT [J].
FRASER, JR ;
BORECKA, B ;
TROTTER, J ;
SHERMAN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1207-1213
[10]   Correlations of structure with binding ability involving nine hemicarcerand hosts and twenty-four guests [J].
Helgeson, RC ;
Knobler, CB ;
Cram, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) :3229-3244