Crucial role of three-center hydrogen bonding in a challenging chiral molecular recognition
SCIE
SCOPUS
- Title
- Crucial role of three-center hydrogen bonding in a challenging chiral molecular recognition
- Authors
- Kim, SG; Kim, KH; Kim, YK; Shin, SK; Ahn, KH
- Date Issued
- 2003-11-12
- Publisher
- AMER CHEMICAL SOC
- Abstract
- The enantio-discrimination of beta-chiral primary ammonium ions is achieved by a rational approach that utilizes three-center (bifurcated) hydrogen bonding. The extraction experiments on various selected guests reveal that the bifurcated H-bonding plays a crucial role for the chiral discrimination. The X-ray data obtained for an inclusion complex substantiate such interactions. Using the bifurcated H-bonding, the chiral molecular recognition with our C-3-symmetric tripodal oxazoline receptors is extended generally toward ammonium ions of alpha-, beta-, and alpha,beta-chiral amines. Simple molecular models, evoking the bifurcated H-bonding, explain the chiral discrimination modes.
- Keywords
- BETA-CYCLODEXTRIN; MODEL SYSTEM; N-H; GEOMETRY; COMPLEXATION; RECEPTORS; BINDING; DNA
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/18252
- DOI
- 10.1021/JA037031P
- ISSN
- 0002-7863
- Article Type
- Article
- Citation
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 125, no. 45, page. 13819 - 13824, 2003-11-12
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