Cavitands with introverted functionality stabilize tetrahedral intermediates.

Cavitands with introverted functionality stabilize tetrahedral intermediates. Research Abstract Details 

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Cavitands with introverted functionality stabilize tetrahedral intermediates. Abstract Text:

Richard J Hooley,Per Restorp,Tetsuo Iwasawa,Julius Rebek,Richard J Hooley,Per Restorp,Tetsuo Iwasawa,Julius Rebek,Richard J Hooley,Per Restorp,Tetsuo Iwasawa,Julius Rebek,

The synthesis and characterization of two deepened cavitand hosts with introverted functionality-functional groups directed into the cavity-is described. Two functions can be introverted, alcohol and aldehyde, and they show the formation of hemiacetals and hemiketals on binding small guests with complementary functional groups. The structures of the bound hemiacetals are determined by 1D and 2D NMR studies. The arrangements of the guests in the cavitands enhance the equilibrium constants of carbonyl additions, K/Kctrl, between 13- and 105-fold, compared to their counterparts in solution. The stabilization of the addition products is due to the prior complexation of the guests and the organized solvation provided to the tetrahedral intermediates by a network of secondary amides at the cavitand rim.

Cavitands with introverted functionality stabilize tetrahedral intermediates. Publishing Authors By Initials

RJ Hooley,P Restorp,T Iwasawa,J Rebek,RJ Hooley,P Restorp,T Iwasawa,J Rebek,RJ Hooley,P Restorp,T Iwasawa,J Rebek,

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Cavitands with introverted functionality stabilize tetrahedral intermediates. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Journal of the American Chemical Society

VOLUME: 129

Page Numbers: 15639-43

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 1520-5126

DAY: 16

MONTH: 11

YEAR: 2007

Cavitands with introverted functionality stabilize tetrahedral intermediates. Information

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LANGUAGE: eng

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AFFILIATION: Contribution from The Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, MB-26, 10550 North Torrey Pines Road, La Jolla, California 92037.

Country: United States

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MEDLINETA: J Am Chem Soc

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