Cucurbit[7]uril host-guest complexes of cholines and phosphonium cholines in aqueous solution.

Content Provider	Semantic Scholar
Author	Wyman, Ian W. Macartney, Donal H.
Copyright Year	2010
Abstract	The neutral host cucurbit[7]uril forms very stable complexes with a series of cationic cholines (R(3)NCH(2)CH(2)OR'(+)) and their phosphonium analogues (R(3)PCH(2)CH(2)OR'(+)) (R(3) = Me(3), Et(3), or Me(2)Bz, or R(3)N = quinuclidinium, and R' = H, COCH(3), CO(CH(2))(2)CH(3), or PO(3)H), and (+/-)-carnitine, in aqueous solution. The complexation behaviour has been investigated using (1)H and (31)P NMR spectroscopies, and ESI mass spectrometry. The complexation-induced chemical shift changes of the guests clearly indicate the effects of replacing the N(CH(3))(3)(+) end group by P(CH(3))(3)(+), and changing the nature of R on the position of the guest with respect to the CB[7] cavity and its polar portal-lining carbonyl groups. This study demonstrates that molecular recognition of cholines in aqueous solution is achievable with a neutral host without the need for aromatic walls for cation-pi interactions.
File Format	PDF HTM / HTML
DOI	10.1039/b917610a
Alternate Webpage(s)	http://www.rsc.org/suppdata/OB/b9/b917610a/b917610a.pdf
PubMed reference number	20024156
Alternate Webpage(s)	https://doi.org/10.1039/b917610a
Journal	Medline
Volume Number	8
Issue Number	1
Journal	Organic & biomolecular chemistry
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article