Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/30417
Title: New C2-symmetric 2,2′-bipyridine crown macrocycles for enantioselective recognition of amino acid derivatives
Authors: Lee, CS
Teng, PF
Wong, WL
Kwong, HL
Chan, ASC
Keywords: Amino acid derivatives
Enantioselectivity
Macrocyclic hosts
Issue Date: 2005
Publisher: Pergamon Press
Source: Tetrahedron, 2005, v. 61, no. 33, p. 7924-7930 How to cite?
Journal: Tetrahedron 
Abstract: A series of new C2-symmetric 2,2′-bipyridine-contaning crown macrocycles 1-4 has been developed for enantiomeric recognition of amino acid derivatives. These new macrocycles have been showed to be strong complexing agents for primary organic ammonium salts (with K up to 4.83×10 5 M-1 and -ΔG0 up to 32.4 kJ mol -1) and also useful chromophores for UV-vis titration studies. These macrocyclic hosts exhibited enantioselective binding towards the (S)-enantiomer of phenylglycine methyl ester hydrochloride (Am1) with K(S)/K (R) up to 2.10 (ΔΔG0=-1.84 kJ mol -1) in CH2Cl2 with 0.25% CH3OH. The structure-binding relationship studies showed that the aromatic subunit and the ester group of the ammonium guests are both important for good enantioselectivity. In addition, the host-guest complexes have been studied using various NMR experiments.
URI: http://hdl.handle.net/10397/30417
ISSN: 0040-4020
DOI: 10.1016/j.tet.2005.06.014
Appears in Collections:Journal/Magazine Article

Access
View full-text via PolyU eLinks SFX Query
Show full item record

SCOPUSTM   
Citations

37
Last Week
0
Last month
0
Citations as of Oct 10, 2017

WEB OF SCIENCETM
Citations

37
Last Week
0
Last month
0
Citations as of Oct 17, 2017

Page view(s)

43
Last Week
8
Last month
Checked on Oct 15, 2017

Google ScholarTM

Check

Altmetric



Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.