Literature DB >> 18989966

Electronic and steric effects in binding of deep cavitands.

Richard J Hooley1, Siddhartha R Shenoy, Julius Rebek.   

Abstract

A deep, self-folding cavitand responds to minor electronic differences between suitably sized adamantane guests. Binding constants range from <0.5 to 4000 M(-1) for guests as similar as 1-bromoadamantane and 1-cyanoadamantane. The barriers to guest exchange also vary up to 3 kcal mol(-1).

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Year:  2008        PMID： 18989966      PMCID： PMC2765558          DOI： 10.1021/ol8022775

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  22 in total

1.  Deep cavitands provide organized solvation of reactions.

Authors:  Richard J Hooley; Julius Rebek
Journal:  J Am Chem Soc       Date:  2005-08-31       Impact factor: 15.419

2.  A deep, water-soluble cavitand acts as a phase-transfer catalyst for hydrophobic species.

Authors:  Richard J Hooley; Shannon M Biros; Julius Rebek
Journal:  Angew Chem Int Ed Engl       Date:  2006-05-19       Impact factor: 15.336

3.  A deep cavitand catalyzes the Diels-Alder reaction of bound maleimides.

Authors:  Richard J Hooley; Julius Rebek
Journal:  Org Biomol Chem       Date:  2007-10-04       Impact factor: 3.876

4.  A combined experimental and theoretical study of the molecular inclusion of organometallic sandwich complexes in a cavitand receptor.

Authors:  Erik Zuidema; M Angeles Sarmentero; Carles Bo; Pablo Ballester
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

5.  Templated assembly of water-soluble nano-capsules: inter-phase sequestration, storage, and separation of hydrocarbon gases.

Authors:  Corinne L D Gibb; Bruce C Gibb
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

6.  Helical folding of alkanes in a self-assembled, cylindrical capsule.

Authors:  Alessandro Scarso; Laurent Trembleau; Julius Rebek
Journal:  J Am Chem Soc       Date:  2004-10-20       Impact factor: 15.419

7.  Extraction of hydrophobic species into a water-soluble synthetic receptor.

Authors:  Richard J Hooley; Hillary J Van Anda; Julius Rebek
Journal:  J Am Chem Soc       Date:  2007-10-10       Impact factor: 15.419

8.  Detection of reactive tetrahedral intermediates in a deep cavitand with an introverted functionality.

Authors:  Richard J Hooley; Tetsuo Iwasawa; Julius Rebek
Journal:  J Am Chem Soc       Date:  2007-11-16       Impact factor: 15.419

9.  Structure-based drug design: exploring the proper filling of apolar pockets at enzyme active sites.

Authors:  Martina Zürcher; François Diederich
Journal:  J Org Chem       Date:  2008-05-30       Impact factor: 4.354

10.  Reactivity and molecular recognition: amine methylation by an introverted ester.

Authors:  Byron W Purse; Pablo Ballester; Julius Rebek
Journal:  J Am Chem Soc       Date:  2003-12-03       Impact factor: 15.419
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  5 in total

1.  Supramolecular architecture with a cavitand-capsule chimera.

Authors:  Agustí Lledó; Seiji Kamioka; Aaron C Sather; Julius Rebek
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-18       Impact factor: 15.336

2.  The ouroborand: a cavitand with a coordination-driven switching device.

Authors:  Fabien Durola; Julius Rebek
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-19       Impact factor: 15.336

3.  Pseudo-capsule assemblies characterized by 19F NMR techniques.

Authors:  Agustí Lledó; Per Restorp; Julius Rebek
Journal:  J Am Chem Soc       Date:  2009-02-25       Impact factor: 15.419

4.  Lipid bilayer environments control exchange kinetics of deep cavitand hosts and enhance disfavored guest conformations.

Authors:  Lizeth Perez; Bethany G Caulkins; Magi Mettry; Leonard J Mueller; Richard J Hooley
Journal:  Chem Sci       Date:  2018-01-11       Impact factor: 9.825

5.  Complexes Between Adamantane Analogues B4X6 -X = {CH2, NH, O ; SiH2, PH, S} - and Dihydrogen, B4X6:nH2 (n = 1-4).

Authors:  Josep M Oliva-Enrich; Ibon Alkorta; José Elguero
Journal:  Molecules       Date:  2020-02-26       Impact factor: 4.411
  5 in total

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