Format

Send to

Choose Destination
Chemistry. 2016 Nov 7;22(46):16356-16398. doi: 10.1002/chem.201601766. Epub 2016 Aug 5.

Resonance-Assisted Hydrogen Bonding as a Driving Force in Synthesis and a Synthon in the Design of Materials.

Author information

1
Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001, Lisboa, Portugal. kamran_chem@mail.ru.
2
Department of Chemistry, Baku State University, Z. Xalilov Str. 23, Az 1148, Baku, Azerbaijan. kamran_chem@mail.ru.
3
Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001, Lisboa, Portugal. pombeiro@tecnico.ulisboa.pt.

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.

KEYWORDS:

conjugation; crystal engineering; hydrogen bonds; pi interactions; synthetic methods

PMID:
27492126
DOI:
10.1002/chem.201601766

Supplemental Content

Loading ...
Support Center