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Intramolecular hydrogen bonding in calixarenes
1The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, CA 92037, USA. dmitry@scripps.edu
Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 14, 2000
Summary
Molecular cavities for recognition and catalysis are built via synthesis or self-assembly. Intramolecular hydrogen bonding controls cavity formation, preorganization, and binding in host molecules like calixarenes.
Area of Science:
- Supramolecular Chemistry
- Organic Chemistry
- Host-Guest Chemistry
Background:
- Constructing molecular cavities for recognition and catalysis typically involves covalent synthesis or intermolecular self-assembly.
- Intramolecular hydrogen bonding offers an alternative strategy to direct the formation and properties of molecular cavities.
- Calixarenes are key building blocks in supramolecular chemistry, known for their cavity-containing structures.
Purpose of the Study:
- To explore the role of intramolecular hydrogen bonding in the formation and function of molecular cavities.
- To discuss the application of this principle in the design of host molecules, particularly calixarene derivatives.
- To highlight how hydrogen bonding influences preorganization and binding capabilities of host molecules.
Main Methods:
- Review of established supramolecular chemistry principles.
- Analysis of case studies involving calixarenes and derived receptor molecules.
- Discussion of molecular design strategies incorporating intramolecular hydrogen bonding.
Main Results:
- Intramolecular hydrogen bonding, when strategically placed, is crucial for the formation and preorganization of molecular cavities.
- This approach enhances the binding ability of host molecules by controlling their conformation.
- Calixarenes serve as excellent platforms for demonstrating the utility of intramolecular hydrogen bonding in host-guest chemistry.
Conclusions:
- Intramolecular hydrogen bonding is a powerful tool for the rational design of molecular cavities.
- It enables precise control over cavity formation, preorganization, and guest binding affinity.
- The principles discussed are broadly applicable to the development of advanced supramolecular receptors and catalysts.
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