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- Title
Resonance-Assisted Hydrogen Bonding as a Driving Force in Synthesis and a Synthon in the Design of Materials.
- Authors
Mahmudov, Kamran T.; Pombeiro, Armando J. L.
- Abstract
Resonance-assisted hydrogen bonding (RAHB), a concept introduced by Gilli and co-workers in 1989, concerns a kind of intramolecular H-bonding strengthened by a conjugated π-system, usually in 6-, 8-, or 10-membered rings. This Review highlights the involvement of RAHB as a driving force in the synthesis of organic, coordination, and organometallic compounds, as a handy tool in the activation of covalent bonds, and in starting moieties for synthetic transformations. The unique roles of RAHB in molecular recognition and switches, E/ Z isomeric resolution, racemization and epimerization of amino acids and chiral amino alcohols, solvatochromism, liquid-crystalline compounds, and in synthons for crystal engineering and polymer materials are also discussed. The Review can provide practical guidance for synthetic chemists that are interested in exploring and further developing RAHB-assisted synthesis and design of materials.
- Subjects
HYDROGEN bonding; ORGANOMETALLIC compounds; ORGANIC synthesis; COVALENT bonds; MOLECULAR recognition; PHYSIOLOGICAL effects of amino acids; EPIMERIZATION; RACEMIZATION
- Publication
Chemistry - A European Journal, 2016, Vol 22, Issue 46, p16356
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201601766