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https://hdl.handle.net/2440/49153
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Type: | Journal article |
Title: | Dimerisation and complexation of 6-(4'-t-butylphenylamino)naphthalene-2-sulphonate by β-cyclodextrin and linked β-cyclodextrin dimers |
Other Titles: | Dimerisation and complexation of 6-(4'-t-butylphenylamino)naphthalene-2-sulphonate by beta-cyclodextrin and linked beta-cyclodextrin dimers |
Author: | Pham, D. Clements, P. Easton, C. Papageorgiou, J. Lincoln, S. May, B. |
Citation: | Supramolecular Chemistry, 2009; 21(6):510-519 |
Publisher: | Gordon Breach Sci Publ Ltd |
Issue Date: | 2009 |
ISSN: | 1061-0278 1029-0478 |
Statement of Responsibility: | Duc-Truc Pham, Philip Clements, Christopher J. Easton, John Papageorgiou, Bruce L. May and Stephen F. Lincoln |
Abstract: | This study shows that stereochemical factors largely determine the extent to which 6-(4′-t-butylphenylamino)-naphthalene-2-sulphonate, BNS− and its dimer, (BNS− )2, are complexed by β-cyclodextrin, βCD, and a range of linked βCD dimers. Fluorescence and 1H NMR studies, respectively, show that BNS− and (BNS− )2 form host–guest complexes with βCD of the stoichiometry βCD.BNS− (10− 4 K 1 = 4.67 dm3 mol− 1) and βCD.BNS2 2 − (10− 2 K 2′ = 2.31 dm3 mol− 1), where the complexation constant K 1 = [βCD.BNS− ]/([βCD][BNS− ]) and K 2′ = [βCD. (BNS− )2]/([βCD.BNS− ][BNS− ]) in aqueous phosphate buffer at pH 7.0, I = 0.10 mol dm3 at 298.2 K. (The dimerisation of BNS− is characterised by 10− 2 K d = 2.65 dm3 mol− 1.) For N,N-bis((2AS,3AS)-3A-deoxy-3A-β-cyclodextrin)succinamide, 33βCD2su, N-((2AS,3AS)-3A-deoxy-3A-β-cyclodextrin)-N′-(6A-deoxy-6A-β-cyclodextrin)urea, 36βCD2su, N,N-bis(6A-deoxy-6A-β-cyclodextrin)succinamide, 66βCD2su, N-((2AS,3AS)-3A-deoxy-3A-β-cyclodextrin)-N′-(6A-deoxy-6A-β-cyclodextrin)urea, 36βCD2ur, and N,N-bis(6A-deoxy-6A-β-cyclodextrin)urea, 66βCD2ur, the analogous 10− 4 K 1 = 11.0, 101, 330, 29.6 and 435 dm3 mol− 1 and 10− 2 K 2′ = 2.56, 2.31, 2.59, 1.82 and 1.72 dm3 mol− 1, respectively. A similar variation occurs in K 1 derived by UV–vis methods. The factors causing the variations in K 1 and K 2 are discussed in conjunction with 1H ROESY NMR and molecular modelling studies. |
Keywords: | cyclodextrin fluorescence host-guest NMR spectroscopy supramolecular |
Description: | Published online: 19 Aug 2009 |
Rights: | Copyright © 2009 Taylor & Francis |
DOI: | 10.1080/10610270802406579 |
Grant ID: | ARC |
Published version: | http://dx.doi.org/10.1080/10610270802406579 |
Appears in Collections: | Aurora harvest Chemistry publications Environment Institute publications |
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