Synthesis and Assembly of Self-Complementary Cavitands

Cavitands with self-complementary shapes (3 and 4) were prepared by the covalent attachment of adamantane guest molecules to the upper rim of the host structures. Relatives of the “self-folding” cavitands 2, these new structures possess a seam of intramolecular hydrogen bonds that stabilize the fold...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 122; no. 19; pp. 4573 - 4582
Main Authors Renslo, Adam R, Tucci, Fabio C, Rudkevich, Dmitry M, Rebek, Julius
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.05.2000
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
O-BENZYNE
DIMERIZE
VESSELS
MOLECULAR RECOGNITION
CAPSULES
ORGANIC MEDIA
HOST-GUEST COMPLEXATION
CARCEPLEXES
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Summary:Cavitands with self-complementary shapes (3 and 4) were prepared by the covalent attachment of adamantane guest molecules to the upper rim of the host structures. Relatives of the “self-folding” cavitands 2, these new structures possess a seam of intramolecular hydrogen bonds that stabilize the folded conformation. Their self-complementary shapes result in the formation of noncovalent dimers of considerable kinetic and thermodynamic stability (−ΔG 295 = 4.5 kcal/mol for 3a and 6.5 kcal/mol for 4a in p-xylene-d 10). The dimerization of cavitands 3 and 4 is reversible and subject to control by solvent and temperature. The dimerization process is enthalpically favored and entropy opposed and occurs with significant enthalpy−entropy compensation.
Bibliography:istex:D2E6C0AD2E8C49BDD7FAD6B9FADA492324FC7E34
ark:/67375/TPS-X7S4P3XF-L
ISSN:0002-7863
1520-5126
DOI:10.1021/ja993922e