Research & Teaching Faculty

Default Header Image

Reversible molecular capsules composed of two cavitands linked via an assortment of charged-hydrogen bonds and covalent bonds

TitleReversible molecular capsules composed of two cavitands linked via an assortment of charged-hydrogen bonds and covalent bonds
Publication TypeJournal Article
Year of Publication1998
AuthorsChapman, RG, Sherman, JC
JournalJournal of the American Chemical Society
Volume120
Pagination9818-9826
Date PublishedSep
Type of ArticleArticle
ISBN Number0002-7863
KeywordsBINDING, carceplex, CHEMISTRY, ENCAPSULATION, HEMICARCERANDS, HOST-GUEST COMPLEXATION, ORGANIC-MOLECULES, RELEASE, TEMPLATION
Abstract

Six new cavitand bowls are reported (6, 7, 8, 9, 11, and 12), as are three bis-bowl compounds (4, 13, and 14). Eight new complexes (4.guest, 7C.guest, 8C.guest, 9C.guest, 14.guest, 15.guest, 15C.guest, and 16C.guest) that reversibly encapsulate small molecules are reported. Two or more charged-hydrogen bonds (CHBs) or covalent linkages between the bowls are required to form stable complexes. Guest exchange rates vary from milliseconds to days. Thermodynamically, these complexes display an enthalpy-entropy compensation. The relative stability of complex 3.pyrazine versus complex 3.chloroform is 170000 in nitrobenzene-d(5) at 298 It. Apparent stability constants in nitrobenzene-d(5) at 298 K yield 1.1 x 10(9) M-1 for complex 3.pyrazine. The absolute stability constant for complex 4.pyrazine in nitrobenzene-d(5) at 333 K is 3.5 x 10(6) M-1.

URL<Go to ISI>://000076225200012