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

[1] Dimeric self-assembling capsules derived from the highly flexible tribenzylamine skeleton [J].

Alajarín, M ;

Pastor, A ;

Orenes, RA ;

Steed, JW .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7091-7095

[2] The Cambridge Structural Database: a quarter of a million crystal structures and rising [J].

Allen, FH .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2002, 58 (3 PART 1) :380-388

[3] Coencapsulation of three different guests in a cylindrical host [J].

Amaya, T ;

Rebek, J .

CHEMICAL COMMUNICATIONS, 2004, (16) :1802-1803

[4] A WELL-BEHAVED ELECTROSTATIC POTENTIAL BASED METHOD USING CHARGE RESTRAINTS FOR DERIVING ATOMIC CHARGES - THE RESP MODEL [J].

BAYLY, CI ;

CIEPLAK, P ;

CORNELL, WD ;

KOLLMAN, PA .

JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (40) :10269-10280

[5] Self-assembly of hydrogen-bonded capsules [J].

Böhmer, V ;

Vysotsky, MO .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2001, 54 (11) :671-677

[6] ENCAPSULATION OF METHANE AND OTHER SMALL MOLECULES IN A SELF-ASSEMBLING SUPERSTRUCTURE [J].

BRANDA, N ;

WYLER, R ;

REBEK, J .

SCIENCE, 1994, 263 (5151) :1267-1268

[7] Intermolecular distance measurements in supramolecular solids:: 13C-19F REDOR NMR spectroscopy of p-tert-butylcalix[4]arene-fluorobenzene [J].

Brouwer, EB ;

Gougeon, RDM ;

Hirschinger, J ;

Udachin, KA ;

Harris, RK ;

Ripmeester, JA .

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 1999, 1 (17) :4043-4050

[8]

Case D.A., 2002, AMBER 7

[9]

Cave GWV, 2001, EUR J ORG CHEM, V2001, P3227

[10]

CAVE GWV, 2004, ANGEW CHEM, V116, P5375

← 1 2 3 4 →