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Literature DB >> 17090022

Molecular recognition and stabilization of iminium ions in water.

Vy M Dong¹, Dorothea Fiedler, Barbara Carl, Robert G Bergman, Kenneth N Raymond.

Abstract

Iminium ions are known to exist only transiently in aqueous solution due to their high reactivity toward hydrolysis. In this communication, we report on the generation and stabilization of iminium ions in aqueous solution via molecular encapsulation using a K12Ga4L6 host. Our studies revealed that tetrahedral host 1 can encapsulate a variety of iminium cations in a molecular recognition process that is selective based on the charge, hydrophobicity, size, and shape of the guest.

Entities: Chemical

Mesh：

Substances：
Imines
Ions
Water

Year: 2006 PMID： 17090022 PMCID： PMC2562236 DOI： 10.1021/ja0657915

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

8 in total

1. Stabilization of a Reactive Cationic Species by Supramolecular Encapsulation Coordination Number Incommensurate Cluster Formation, Part 15. This research was supported by NSF grant CHE-9709621. We gratefully acknowledge Prof. Julie A. Leary and Dr. Ulla Andersen for their assistance with mass spectrometry. We also thank the Miller Foundation for a postdoctoral fellowship to M.Z. and the NIH for a postdoctoral fellowship to J.L.B. Part 14: J. Xide, K. N. Raymond, Angew. Chem. 2000, 112, 2857-2859; Angew. Chem. Int. Ed. 2000, 39, 2745-2747.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-11-17 Impact factor: 15.336

Review 2. Self-assembled nanoreactors.

Authors: Dennis M Vriezema; Marta Comellas Aragonès; Johannes A A W Elemans; Jeroen J L M Cornelissen; Alan E Rowan; Roeland J M Nolte
Journal: Chem Rev Date: 2005-04 Impact factor: 60.622

3. Selective molecular recognition, C-H bond activation, and catalysis in nanoscale reaction vessels.

Authors: Dorothea Fiedler; Dennis H Leung; Robert G Bergman; Kenneth N Raymond
Journal: Acc Chem Res Date: 2005-04 Impact factor: 22.384

4. Stabilization of reactive organometallic intermediates inside a self-assembled nanoscale host.

Authors: Dorothea Fiedler; Robert G Bergman; Kenneth N Raymond
Journal: Angew Chem Int Ed Engl Date: 2006-01-23 Impact factor: 15.336

5. Virtual combinatorial libraries: dynamic generation of molecular and supramolecular diversity by self-assembly.

Authors: I Huc; J M Lehn
Journal: Proc Natl Acad Sci U S A Date: 1997-03-18 Impact factor: 11.205

6. Design, formation and properties of tetrahedral M(4)L(4) and M(4)L(6) supramolecular clusters.

Authors: D L Caulder; C Brückner; R E Powers; S König; T N Parac; J A Leary; K N Raymond
Journal: J Am Chem Soc Date: 2001-09-19 Impact factor: 15.419

7. Helical conformation of alkanes in a hydrophobic cavitand.

Authors: Laurent Trembleau; Julius Rebek
Journal: Science Date: 2003-08-29 Impact factor: 47.728

8. Self-fulfilling cavitands: packing alkyl chains into small spaces.

Authors: Byron W Purse; Julius Rebek
Journal: Proc Natl Acad Sci U S A Date: 2006-02-13 Impact factor: 11.205

8 in total

24 in total

1. Adaptations of guest and host in expanded self-assembled capsules.

Authors: Dariush Ajami; Julius Rebek
Journal: Proc Natl Acad Sci U S A Date: 2007-10-02 Impact factor: 11.205

2. Molecular recognition and self-assembly special feature: Disproportionation and self-sorting in molecular encapsulation.

Authors: Dariush Ajami; Jun-Li Hou; Trevor J Dale; Elizabeth Barrett; Julius Rebek
Journal: Proc Natl Acad Sci U S A Date: 2009-02-27 Impact factor: 11.205

Review 3. High-definition self-assemblies driven by the hydrophobic effect: synthesis and properties of a supramolecular nanocapsule.

Authors: Simin Liu; Bruce C Gibb
Journal: Chem Commun (Camb) Date: 2008-06-06 Impact factor: 6.222

Molecular recognition and stabilization of iminium ions in water.

Review 2. Self-assembled nanoreactors.

3. Selective molecular recognition, C-H bond activation, and catalysis in nanoscale reaction vessels.

4. Stabilization of reactive organometallic intermediates inside a self-assembled nanoscale host.

5. Virtual combinatorial libraries: dynamic generation of molecular and supramolecular diversity by self-assembly.

6. Design, formation and properties of tetrahedral M(4)L(4) and M(4)L(6) supramolecular clusters.

7. Helical conformation of alkanes in a hydrophobic cavitand.

8. Self-fulfilling cavitands: packing alkyl chains into small spaces.

1. Adaptations of guest and host in expanded self-assembled capsules.

2. Molecular recognition and self-assembly special feature: Disproportionation and self-sorting in molecular encapsulation.

Review 3. High-definition self-assemblies driven by the hydrophobic effect: synthesis and properties of a supramolecular nanocapsule.

4. Reaction of isonitriles with carboxylic acids in a cavitand: observation of elusive isoimide intermediates.

Review 5. Supramolecular coordination: self-assembly of finite two- and three-dimensional ensembles.

6. Two-component control of guest binding in a self-assembled cage molecule.

Review 7. The Cation-π Interaction in Small-Molecule Catalysis.

8. Design and Applications of Water-Soluble Coordination Cages.

9. Compressed alkanes in reversible encapsulation complexes.

10. Interaction energies and dynamics of acid-base pairs isolated in cavitands.