Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/4818
Citations | ||
Scopus | Web of Science® | Altmetric |
---|---|---|
?
|
?
|
Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Field, M. | - |
dc.contributor.author | May, B. | - |
dc.contributor.author | Clements, P. | - |
dc.contributor.author | Tsanaktsidis, J. | - |
dc.contributor.author | Easton, C. | - |
dc.contributor.author | Lincoln, S. | - |
dc.date.issued | 2000 | - |
dc.identifier.citation | Organic and Biomolecular Chemistry, 2000; 8(8):1251-1258 | - |
dc.identifier.issn | 1472-7781 | - |
dc.identifier.issn | 1470-4358 | - |
dc.identifier.uri | http://hdl.handle.net/2440/4818 | - |
dc.description | Copyright © 2000 The Royal Society of Chemistry | - |
dc.description.abstract | The reactions of 4-nitrophenyl trinorbornane-2-acetate and 4-nitrophenyl noradamantane-1-carboxylate with 6A-(6-aminohexyIamino)-6A-deoxy-β-cyclodextrin l produce 6A-{6-(bicyclo[2.2.l]heptan-2-ylacetylamino)hexylamino}-6 A-deoxy-β-cyclodextrin 2 (pKa = 8.98) and 6A-deoxy-6A-{6-(tricyclo[3.3.1.0 3.7]nonan-3-ylcarbonylamino)-hexylamino}-β-cyclodextrin 4 (pKa = 8.47), respectively, in good yield together with 4-nitrophenolate. The reaction of 2,3-dimethyl-1,8-bis-(4-nitrophenoxycarbonyl)cubane with two moles of 1 produces dimeric 1,8-bis-[6-(6Adeoxy-β-cyclodextrin-6 A-ylamino)hexylaminocarbonyl]-2,3-dimethylcubane 7 (pK, = 8.80) in good yield together with two moles of 4-nitrophenolate. The pKa in brackets are those of the single protonated amine functions of 2 and 4, and of both protonated amine functions of 7 which have identical pATas [in each case at 298.2 K and I = 0.10 mol dm-3 (NaClO4)]. 1H NMR ROESY studies are consistent with the trinorbornyl, noradamantyl and dimethylcubyl entities of 2,4 and 7 complexing inside the βCD annuli in D2O at pD ≥ 11. Under the same conditions, adamantane-1-carboxylate forms intermolecular complexes with 2,4 and 7 and displaces their trinorbornyl, noradamantyl and the dimethylcubyl entities from the β-cyclodextrin annulus to varying degrees depending on the relative size, shape and hydrophobicity of these groups. These data are compared with those for analogous modified β-cyclodextrins. © The Royal Society of Chemistry 2000. | - |
dc.description.statementofresponsibility | Michael J. Field, Bruce L. May, Philip Clements, John Tsanaktsidis, Christopher J. Easton and Stephen F. Lincoln | - |
dc.language.iso | en | - |
dc.publisher | Royal Society of Chemistry | - |
dc.source.uri | http://dx.doi.org/10.1039/a909766j | - |
dc.title | Intramolecular complexation in modified b-cyclodextrins: a preparative, nuclear magnetic resonance and pH titration study | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1039/a909766j | - |
pubs.publication-status | Published | - |
Appears in Collections: | Aurora harvest 6 Chemistry publications Environment Institute publications |
Files in This Item:
There are no files associated with this item.
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.