Hydrogen-bonded encapsulation complexes in protic solvents

被引:24
作者
Amaya, T [1 ]
Rebek, J [1 ]
机构
[1] Scripps Res Inst, Dept Chem, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
关键词
D O I
10.1021/ja0467770
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We describe here the behavior of the hydrogen-bonded capsule 1(.)1 and its complexes in protic solvents. The kinetics and thermodynamics of the encapsulation process were determined through conventional H-1 NMR methods. The enthalpies and entropies of encapsulation are both positive, indicating a process that liberates solvent molecules. The rates of dissociation-association of the capsule were comparable to the rates for the in-out exchange of large guests, which suggests that guest exchange occurs by complete dissociation of the capsule in protic solvents. The stability of the hydrogen-bonded capsule 1(.)1 toward protic solvents depends strongly on the guests, with the best guest being dimethylstilbene 8. The results establish guidelines for the properties of capsules that could be accessed in water.
引用
收藏
页码:14149 / 14156
页数:8
相关论文
共 45 条
[1]   TWO-DIMENSIONAL NMR EXCHANGE SPECTROSCOPY - QUANTITATIVE TREATMENT OF MULTISITE EXCHANGING SYSTEMS [J].
ABEL, EW ;
COSTON, TPJ ;
ORRELL, KG ;
SIK, V ;
STEPHENSON, D .
JOURNAL OF MAGNETIC RESONANCE, 1986, 70 (01) :34-53
[2]   Hydrogen-bonded molecular capsules are stable in polar media [J].
Atwood, JL ;
Barbour, LJ ;
Jerga, A .
CHEMICAL COMMUNICATIONS, 2001, (22) :2376-2377
[3]   CONTROL OF SELF-ASSEMBLY AND REVERSIBLE ENCAPSULATION OF XENON IN A SELF-ASSEMBLING DIMER BY ACID-BASE CHEMISTRY [J].
BRANDA, N ;
GROTZFELD, RM ;
VALDES, C ;
REBEK, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) :85-88
[4]   ORGANIC-MOLECULES DIMERIZE WITH HIGH STRUCTURAL RECOGNITION WHEN EACH POSSESSES A LARGE LIPOPHILIC SURFACE CONTAINING 2 PREORGANIZED AND COMPLEMENTARY HOST AND GUEST REGIONS [J].
BRYANT, JA ;
KNOBLER, CB ;
CRAM, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (03) :1254-1255
[5]   HIGH PREORGANIZATION OF LARGE LIPOPHILIC SURFACES COMMON TO 2 COMPLEXING PARTNERS PROVIDES HIGH BINDING FREE-ENERGIES THAT VARY DRAMATICALLY WITH CHANGES IN ORGANIC-SOLVENT COMPOSITION [J].
BRYANT, JA ;
ERICSON, JL ;
CRAM, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (03) :1255-1256
[6]   Detection and mechanistic studies of multicomponent assembly by fluorescence resonance energy transfer [J].
Castellano, RK ;
Craig, SL ;
Nuckolls, C ;
Rebek, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) :7876-7882
[7]   Supermolecules by design [J].
Caulder, DL ;
Raymond, KN .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (11) :975-982
[8]   Extreme complementarity in a Macrocycle-Tweezer complex [J].
Colquhoun, HM ;
Zhu, ZX ;
Williams, DJ .
ORGANIC LETTERS, 2003, 5 (23) :4353-4356
[9]   Self-assembling capsules [J].
Conn, MM ;
Rebek, J .
CHEMICAL REVIEWS, 1997, 97 (05) :1647-1668
[10]   Guest encapsulation in a water-soluble molecular capsule based on ionic interactions [J].
Corbellini, F ;
Di Costanzo, L ;
Crego-Calama, M ;
Geremia, S ;
Reinhoudt, DN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (33) :9946-9947