Self-assembling sieves

Angewandte Chemie - International Edition

Volumn 37, Issue 24, 1999, Pages 3410-3413

  Szabo, Tomas ^a   O'Leary, Brendan M ^a   Rebek, Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Host guest chemistry; Hydrogen bonds; Self assembly; Supramolecular chemistry

Indexed keywords

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

EID: 0033521668     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981231)37:24<3410::AID-ANIE3410>3.0.CO;2-1     Document Type: Article

References (28)

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9. Prepared analogously to the corresponding ethyl ester, see: J. Villieras, M. Rambaud, Synthesis 1982, 924-926.
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17. All new compounds were characterized by high-resolution NMR spectroscopy and mass spectrometry.
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19. 6.
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22. S. Mecozzi, J. Rebek, Jr., Chem. Eur. J. 1998, 4, 1016-1022. Cavity volumes likely are underestimated due to the necessary hole-blocking method used in calculations. Therefore, PCs will appear larger than the reported ideal. The best binders in this study gave an apparent average PC = 0.59 × 0.09. [PC = volume of guest(s)/volume of cavity].
23. Modeling was performed by using a Macromodel v5.5, Amber force-field. Pore blocking was necessary to define a cavity. This involved replacing the equatorial hydrogen atoms on each module's six-membered ring with a cyclopropyl group. Volumes are based upon a static structure and calculated as described in reference [15].
24. The twelve phenyl groups of the glycolurils present their edges to the cavity which accounts for the downfield shifts of guests' signals from their "free" positions.
25. Ferrocene derivatives were modeled by using MacSpartan Plus and their volumes were calculated by using MacroModel.
26. 12]mesitylene. This probably results from the poor shape co jnplementarity of two encapsulated mesitylenes (PCs = 0.57 and 0.51, respectively) with the cavities.
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