TY - JOUR
T1 - Synthesis and conformational analysis of an a-cyclodextrin [2]-rotaxane
AU - Easton, Christopher J.
AU - Lincoln, Stephen F.
AU - Meyer, Adam G.
AU - Onagi, Hideki
PY - 1999
Y1 - 1999
N2 - An a-cyclodextrin [2]-rotaxane has been prepared in 10% yield, by threading a-cyclodextrin (a-CD) with (£)-4, 4'diaminostilbene in aqueous solution and capping the included guest through reaction with 2, 4, 6-trinitrobenzene-lsulfonate. ID 'H NMR spectroscopy and DQCOSY and ROES Y experiments show that the a-CD rotates freely around the axle of the rotaxane, but is localised over the olefinic moiety of the stilbene. The pA"a values of the a-CD [2]-rotaxane were found to be 9.3 and 9.6, which are attributable to deprotonations of the (£')-4)4'-bis(2, 4, 6-trinitrophenylamino)stilbene moiety. NMR experiments show that these deprotonations do not perturb the conformation of the rotaxane.
AB - An a-cyclodextrin [2]-rotaxane has been prepared in 10% yield, by threading a-cyclodextrin (a-CD) with (£)-4, 4'diaminostilbene in aqueous solution and capping the included guest through reaction with 2, 4, 6-trinitrobenzene-lsulfonate. ID 'H NMR spectroscopy and DQCOSY and ROES Y experiments show that the a-CD rotates freely around the axle of the rotaxane, but is localised over the olefinic moiety of the stilbene. The pA"a values of the a-CD [2]-rotaxane were found to be 9.3 and 9.6, which are attributable to deprotonations of the (£')-4)4'-bis(2, 4, 6-trinitrophenylamino)stilbene moiety. NMR experiments show that these deprotonations do not perturb the conformation of the rotaxane.
UR - http://www.scopus.com/inward/record.url?scp=0001374997&partnerID=8YFLogxK
U2 - 10.1039/a902176k
DO - 10.1039/a902176k
M3 - Article
SN - 1472-7781
SP - 2501
EP - 2506
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 17
ER -