Inclusion of quinolines by binaphthol: structures and selectivity
- 3 February 2004
- journal article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 2 (5) , 655-659
- https://doi.org/10.1039/b314691j
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).Keywords
This publication has 1 reference indexed in Scilit:
- X-Seed — A Software Tool for Supramolecular CrystallographyJournal of Supramolecular Chemistry, 2001