Orientational preferences of aromatic guests in dimeric capsules of tetraurea calix[4]arenes -: MD and NMR studies

被引：10

作者：

Broda, Frank

Vysotsky, Myroslav O.

Boehmer, Volker ^{[1
]}

Thondorf, Iris

机构：

[1] Johannes Gutenberg Univ Mainz, Fachbereich Chem Pharm & Geowissensch, Abt Lehramt Chem, D-55099 Mainz, Germany

[2] Univ Halle Wittenberg, Fachbereich Biochem Biotechnol, D-06120 Halle, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 12期

关键词：

D O I：

10.1039/b604235j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Molecular dynamics (MD) simulations have been performed for complexes of a dimeric capsule of a tetraurea calixarene with a series of twelve aromatic guests. A distinct orientational preference and a restriction of the internal mobility was found which depend on the size and electronic properties of the guests. The results are in agreement with the CIS values obtained from H-1 NMR spectroscopic measurements and with complexation selectivities obtained by competition experiments.

引用

页码：2424 / 2432

页数：9

共 40 条

[11] Templation and encapsulation in supramolecular chemistry [J].

Chapman, RG ;

Sherman, JC .

TETRAHEDRON, 1997, 53 (47) :15911-15945

[12] Crystal structure and thermodynamics of reversible molecular capsules [J].

Chapman, RG ;

Olovsson, G ;

Trotter, J ;

Sherman, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (25) :6252-6260

[13]

HAMANN BC, 1996, ANGEW CHEM, V108, P1425, DOI DOI 10.1002/ANIE.199613261

[14]

Hof F., 2002, ANGEW CHEM, V114, P1556

[15] Attractive intramolecular edge-to-face aromatic interactions in flexible organic molecules [J].

Jennings, WB ;

Farrell, BM ;

Malone, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (11) :885-894

[16]

JOHNSON DW, 2002, ANGEW CHEM, V114, P3947

[17] Guest-induced assembly of tetracarboxyl-cavitand and tetra(3-pyridyl)-cavitand into a heterodimeric capsule via hydrogen bonds and CH-halogen and/or CH-π interaction:: Control of the orientation of the encapsulated guest [J].

Kobayashi, K ;

Ishii, K ;

Sakamoto, S ;

Shirasaka, T ;

Yamaguchi, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (35) :10615-10624

[18] Molecular capsule constructed by multiple hydrogen bonds: self-assembly of cavitand tetracarboxylic acid with 2-aminopyrimidine [J].

Kobayashi, K ;

Shirasaka, T ;

Yamaguchi, K ;

Sakamoto, S ;

Horn, E ;

Furukawa, N .

CHEMICAL COMMUNICATIONS, 2000, (01) :41-42

[19]

Mecozzi S, 1998, CHEM-EUR J, V4, P1016, DOI 10.1002/(SICI)1521-3765(19980615)4:6<1016::AID-CHEM1016>3.0.CO

[20]

2-B

← 1 2 3 4 →