Achiral Molecular Recognition of Substituted Aniline Position Isomers by Crown Ether Type Chiral Stationary Phase
Keyword(s):
To understand the selectivity of the crown ether type chiral stationary phase (CSP), the retention selectivity for aniline and the positional isomers of substituted anilines were studied. In various substituted isomers, except nitroaniline, a remarkable decrease of retention due to steric hindrance was observed for the 2-substituted isomer. To determine the detailed molecular recognition mechanism, quantum chemical calculations were performed for the aggregates between the crown ether and the anilines. The results suggested that the 20-Crown-6, which includes a phenyl-substituted 1,1′-binaphthyl moiety, interacts with alkyl and aryl amines in an unconventional form different from the proposed one for 18-Crown-6.
2010 ◽
Vol 33
(9)
◽
pp. 1419-1423
◽
2006 ◽
Vol 17
(12)
◽
pp. 1883-1889
◽
Keyword(s):
Enantiomer separation of amino compounds by a novel chiral stationary phase derived from crown ether
1998 ◽
Vol 805
(1-2)
◽
pp. 85-92
◽
Keyword(s):
2009 ◽
Vol 32
(7)
◽
pp. 981-987
◽
1996 ◽
Vol 737
(2)
◽
pp. 157-169
◽
Keyword(s):
2019 ◽
Vol 117
(23-24)
◽
pp. 3569-3588
◽