Molecular Encapsulation

Organic Reactions in Constrained Systems
Ed. by Brinker, Udo H.; Mieusset, Jean-Luc

• Gebundenes Buch

Produktbeschreibung

The inclusion of small guest molecules within suitable host compounds results in constrained systems that imbue novel properties upon the incarcerated organic substrates. Supramolecular tactics are becoming widely employed and this treatise spotlights them. Often, the impact of encapsulation on product formation is substantial. The use of constrained systems offers the means to steer reactions along desired pathways. A broad overview of various supramolecular approaches aimed to manipulate chemical reactions are featured.
The following topics are covered in detail:

- general concepts governing the assembly of the substrate with the reaction vessel

- preparation of molecular reactors

- stabilization of reactive intermediates

- reactions in water, in organic solvents, and in the solid state

- photochemical reactions

- reactions with unusual regioselectivity

Molecular Encapsulation: Organic Reactions in Constrained Systems is an essential guide to the art of changing the outcome and the selectivity of a chemical reaction using nano-sized reaction vessels. It will find a place on the bookshelves of students and researchers working in the areas of supramolecular chemistry, nanotechnology, organic and pharmaceutical chemistry, and materials science as well.

Produktdetails

• Verlag: Wiley & Sons
• Artikelnr. des Verlages: 14599807000
• 1. Auflage
• Seitenzahl: 520
• Erscheinungstermin: 9. August 2010
• Englisch
• Abmessung: 253mm x 177mm x 37mm
• Gewicht: 1019g
• ISBN-13: 9780470998076
• ISBN-10: 0470998075
• Artikelnr.: 29927927

Autorenporträt

Dr. Udo H. Brinker, University Professor; Head of Research Group for Physical Organic Chemistry and Structural Chemistry, Institute of Organic Chemistry, University of Vienna; and Research Professor of Chemistry at State University of New York at Binghamton, NY, USA. Dr. Jean-Luc Mieusset, University Assistant, Institute of Organic Chemistry, University of Vienna.

Inhaltsangabe

Preface page. List of Contributors. 1 Reaction Control by Molecular
Recognition - A Survey from the Photochemical Perspective (Cheng Yang,
Chenfeng Ke, Yu Liu, and Yoshihisa Inoue). 1.1 Introduction. 1.2
Photochemical Reactions Mediated by Macrocyclic Compounds. 1.3
Photochemical Reactions with Biomolecules. 1.4 Photochemical Reactions with
Confined Cages Based on Inorganic and Organic-Inorganic Hybrid Materials.
1.5 Photochemical Reactions with other Artificial Hosts. 1.6 Photoreaction
Control by External Variants. 1.7 Conclusions. 2 Cyclodextrins (Ronald
Breslow). 2.1 Introduction. 2.2 Acylations of the Cyclodextrins by Bound
Substrates. 2.3 Catalytic Reactions in Cyclodextrin Cavities: Aromatic
Substitution. 2.4 Other Solvents than Water. 2.5 Catalytic Reactions
Produced by Cyclodextrins With Covalently Attached Catalytic Groups. 2.6
Binding by Cyclodextrins and their Dimers and Trimers. 2.7 Mimics of
Enzymes that Use Thiamine Pyrophosphate as a Co-Enzyme. 2.8 Aldol
Condensations Catalysed by Cyclodextrin Derivatives. 2.9 Mimics of Enzymes
Using Coenzyme B12 as a Cofactor. 2.10 Mimics of Cytochrome P-450. 3
Cyclodextrins as Molecular Reactors (Christopher J. Easton and Hideki
Onagi). 3.1 Introduction. 3.2 Regiocontrolled Electrophilic Aromatic
Substitutions. 3.3 Catalysis of Hydrolytic Reactions. 3.4 A Molecular
Reactor for the Synthesis of Indigoid Dyes. 3.5 Manipulation of
Cycloadditions. 3.6 Conclusion. 4 Reactions Mediated by Cyclodextrins
(Keiko Takahashi). 4.1 Introduction. 4.2 The Inclusion Phenomena of
Cyclodextrins. 4.3 Origin of Microvessels as Molecular Flasks. 4.4 Organic
Reactions Mediated by CD in Water. 4.5 Conclusion. 5 Reactions in Zeolites
(Stéphane Walspurger and Jean Sommer). 5.1 The Confi nement Effect. 5.2
Superelectrophilic Activation in Zeolites. 5.3 Huisgen
[3+2]-Cycloadditions. 5.4 Multicomponent Reactions. 5.5 Conclusion. 6
Chemistry in Self-Assembled Nanoreactors (Jarl Ivar van der Vlugt, Tehila
S. Koblenz, Jeroen Wassenaar, and Joost N. H. Reek). 6.1 Introduction. 6.2
Self-Assembled Nanocapsules. 6.3 Encapsulation Effects in Catalysis. 6.4
Hydrogen Bonded Capsules. 6.5 Capsules Based on Metal-Ligand Interactions.
6.6 Tetrahedral Cages Based on Octahedral M3+ Ions. 6.7 Octahedral and
Square Pyramidal Cages Based on Square-Planar M2+ Ions. 6.8 Hydrophobic
Effects as the Driving Force for the Self-Assembly of Nanocapsules. 6.9
Ligand Template Approach Using Lewis Acid/Base Interactions. 6.10 Virus
Capsids, Proteins and Micellar Systems. 6.11 Micellar Systems. 6.12
Conclusions and Outlook. 7 Concave Reagents (Ulrich Lüning). 7.1
Introduction. 7.2 Classes of Concave Reagents. 7.3 Reactions and Catalyses.
7.4 Summary and Outlook. 8 Reactivity Control by Calixarenes (Luigi
Mandolini, Roberta Cacciapaglia, and Stefano Di Stefano). 8.1 Introduction.
8.2 Calixarenes as Hosts. 8.3 Calixarenes as Molecular Platforms. 8.4
Concluding Remarks. 9 Reactions Inside Carcerands (Ralf Warmuth). 9.1
Introduction. 9.2 Types of Inner Phase Reactions. 9.3 Probing the
Properties of the Inner Phase. 9.4 Through-Shell Reactions. 9.5
Intramolecular Thermal Reactions. 9.6 Inner Phase Photochemistry. 9.7
Conclusions and Outlook. 10 Encapsulation of Reactive Intermediates
(Jean-Luc Mieusset and Udo H. Brinker). 10.1 Introduction. 10.2
Encapsulation of Labile Species. 10.3 Isolation of Non-covalently Bonded
Aggregates. 10.4 Inclusion of Reactive Intermediates. 11 Dye Encapsulation
(Jeremiah J. Gassensmith, Easwaran Arunkumar, and Bradley D. Smith). 11.1
Introduction. 11.2 Reversible Dye Encapsulation Inside Organic Container
Molecules. 11.3 Reversible Dye Encapsulation by Biological Receptors. 11.4
Permanent Dye Encapsulation Inside Rotaxanes. 11.5 Permanent Encapsulation
Inside Inorganic Matrices. 11.6 Conclusion. 12 Organic Cations in
Constrained Systems (Werner Abraham and Lutz Grubert). 12.1 Introduction.
12.2 Host-guest Complexes with Organic Cations. 12.3 Extended Hosts and
Capsules. 12.4 Cucurbiturils. 12.5 Complex Systems and Applications. 12.6
Conclusions. 13 Proteins as Host for Enantioselective Catalysis: Artificial
Metalloenzymes Based on the Biotin-Streptavidin Technology (Jincheng Mao
and Thomas R. Ward). 13.1 Introduction. 13.2 The Biotin-Avidin Technology.
13.3 Artifi cial Hydrogenases. 13.4 Artifi cial Allylic Alkylases. 13.5
Artifi cial Transfer Hydrogenase. 13.6 Enantioselective Sulfoxidation Based
on Vanadyl-loaded Streptavidin 372 13.7 Conclusions and Outlook. 14
Chemical Reactions with RNA and DNA Enzymes (Andres Jäschke). 14.1
Introduction. 14.2 Catalysis by Naturally Occurring Ribozymes. 14.3 How to
Generate Artifi cial RNA and DNA Catalysts. 14.4 The Catalytic Spectrum of
Artifi cial Ribozymes. 14.5 Deoxyribozymes - DNA Molecules with Catalytic
Properties. 14.6 Catalysis of C-C Bond Formation by Diels-Alderase
Ribozymes. 14.7 Conclusion. 15 Reactions in Supramolecular Systems (Lucia
Zakharova, Alla Mirgorodskaya, Elena Zhiltsova, Ludmila Kudryavtseva, and
Alexander Konovalov). 15.1 Introduction. 15.2 The Single Micellar Systems:
Factors of Concentration and Micellar Microenvironment. 15.3 The Role of
the Structural Factor in Supramolecular Catalytic Systems. 15.4 Binary
Surfactant Systems. 15.5 Polycomponent Catalytic Systems Based on
Amphiphiles and Polymers. 15.6 Conclusions. 16 Encapsulation Processes by
Bilayer Vesicles (Marc C. A. Stuart and Jan B. F. N. Engberts). 16.1
Introduction. 16.2 Catalysis by Vesicles. Encapsulation of Reactants. 16.3
Liposomal Encapsulation in Drug Delivery. 16.4 Vesicle-Nucleic Acid
Interactions: Gene Transfer Using Lipoplexes. 17 Reactions in Liposomes
(Pasquale Stano and Pier Luigi Luisi). 17.1 Introduction. 17.2 Lipid
Vesicles (Liposomes). 17.3 Experimental Strategies and Theoretical Aspects.
17.4 A Theoretical Framework for Complex Reactions in Liposomes. 17.5 Four
Cases of Compartmentalized Reactions. 17.6 Conclusion. Acknowledgements.
Abbreviations. References. Index.