Issue 5, 2004

Inclusion of quinolines by binaphthol: structures and selectivity

Abstract

The enclathration selectivity of the host compound 2,2′-dihydroxyl-1,1′-binaphthyl, BINAP, towards the guests quinoline (Q), 2-methylquinoline (2MeQ), 6-methylquinoline (6MeQ) and 8-methylquinoline (8MeQ) were established by competition experiments as: BINAP·2(2MeQ) > BINAP·2Q > BINAP·2(8MeQ) > BINAP·2.5(6MeQ). The crystal structures of the inclusion compounds were elucidated and are all stabilised by (host)O–H⋯N(guest) hydrogen bonds. Thermal analysis yields the same sequence with respect to the relative stabilities. pH Control was employed to dramatically modify the selectivity profile of the pair of 2-methylquinoline (2MeQ) and 8-methylquinoline (8MeQ).

Graphical abstract: Inclusion of quinolines by binaphthol: structures and selectivity

Supplementary files

Article information

Article type
Paper
Submitted
14 Nov 2003
Accepted
07 Jan 2004
First published
03 Feb 2004

Org. Biomol. Chem., 2004,2, 655-659

Inclusion of quinolines by binaphthol: structures and selectivity

M. R. Caira, Y. Paul Chang, L. R. Nassimbeni and H. Su, Org. Biomol. Chem., 2004, 2, 655 DOI: 10.1039/B314691J

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