Hydration of isocyanates in an expandable, self-assembled capsule.

A self-assembled capsule facilitates reactions of isocyanates with water. The capsule provides an amphiphilic environment with hydrophobic aromatic ends and hydrophilic glycoluril units at the center. Reaction takes place in the narrow, cylindrical space to form the N,N-dialkylurea, which then appears in a longer capsule.

[1]  M. Fujita,et al.  Cage-catalyzed Knoevenagel condensation under neutral conditions in water. , 2012, Journal of the American Chemical Society.

[2]  Orion B. Berryman,et al.  Reactivity of N-nitrosoamides in confined spaces , 2011 .

[3]  C. Mirkin,et al.  Enzyme mimics based upon supramolecular coordination chemistry. , 2011, Angewandte Chemie.

[4]  C. Mirkin,et al.  Allosteric Supramolecular Triple-Layer Catalysts , 2010, Science.

[5]  S. Rick,et al.  Kinetic resolution of constitutional isomers controlled by selective protection inside a supramolecular nanocapsule. , 2010, Nature chemistry.

[6]  J. Rebek,et al.  Multicomponent, hydrogen-bonded cylindrical capsules. , 2009, The Journal of organic chemistry.

[7]  J. Rebek.  Molecular behavior in small spaces. , 2009, Accounts of chemical research.

[8]  Robert G. Bergman,et al.  Proton-mediated chemistry and catalysis in a self-assembled supramolecular host. , 2009, Accounts of chemical research.

[9]  M. Fujita,et al.  Functional molecular flasks: new properties and reactions within discrete, self-assembled hosts. , 2009, Angewandte Chemie.

[10]  J. Rebek,et al.  Compressed alkanes in reversible encapsulation complexes. , 2009, Nature chemistry.

[11]  S. Arroyo,et al.  Theoretical study of the neutral hydrolysis of hydrogen isocyanate in aqueous solution via assisted-concerted mechanisms. , 2009 .

[12]  Joost N H Reek,et al.  Reactivity within a confined self-assembled nanospace. , 2008, Chemical Society reviews.

[13]  J. Rebek,et al.  Longer guests drive the reversible assembly of hyperextended capsules. , 2007, Angewandte Chemie.

[14]  J. Rebek,et al.  Adaptations of guest and host in expanded self-assembled capsules , 2007, Proceedings of the National Academy of Sciences.

[15]  Heidi M. Muchall,et al.  Hydrolysis of N-sulfinylamines and isocyanates: a computational comparison. , 2007, The journal of physical chemistry. A.

[16]  Michael D. Pluth,et al.  Acid Catalysis in Basic Solution: A Supramolecular Host Promotes Orthoformate Hydrolysis , 2007, Science.

[17]  Michael D. Pluth,et al.  Reversible guest exchange mechanisms in supramolecular host-guest assemblies. , 2006, Chemical Society reviews.

[18]  M. Tamura,et al.  Diels-Alder in Aqueous Molecular Hosts: Unusual Regioselectivity and Efficient Catalysis , 2006, Science.

[19]  J. Rebek,et al.  Expanded capsules with reversibly added spacers. , 2006, Journal of the American Chemical Society.

[20]  Johannes A A W Elemans,et al.  Self-assembled nanoreactors. , 2005, Chemical reviews.

[21]  J. Rebek,et al.  The ins and outs of molecular encapsulation. , 2004, Organic & biomolecular chemistry.

[22]  B. Gibb,et al.  Well-defined, organic nanoenvironments in water: the hydrophobic effect drives a capsular assembly. , 2004, Journal of the American Chemical Society.

[23]  J. Rebek,et al.  An NMR study of the rates of single-molecule exchange in a cylindrical host capsule. , 2002, Journal of the American Chemical Society.

[24]  H. Ni,et al.  Effect of catalysts on the reaction of an aliphatic isocyanate and water , 2002 .

[25]  J. Rebek,et al.  Selectivity in an encapsulated cycloaddition reaction. , 2002, Organic letters.

[26]  K. Raymond,et al.  Stabilization of a Reactive Cationic Species by Supramolecular Encapsulation , 2000 .

[27]  T. Ziegler,et al.  Preparation of Bioconjugates through an Ugi Reaction , 2000 .

[28]  J. Rebek,et al.  The 55 % Solution: A Formula for Molecular Recognition in the Liquid State , 1998 .

[29]  E. E. Gruber,et al.  Mechanism of the Water-lsocyanate Reaction , 1960 .