Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/4705
Citations | ||
Scopus | Web of Science® | Altmetric |
---|---|---|
?
|
?
|
Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Redman, K. | - |
dc.contributor.author | May, B. | - |
dc.contributor.author | Kean, S. | - |
dc.contributor.author | Clements, P. | - |
dc.contributor.author | Easton, C. | - |
dc.contributor.author | Lincoln, S. | - |
dc.date.issued | 1999 | - |
dc.identifier.citation | Journal of the Chemical Society, Perkin Transactions 2, 1999; 8(8):1711-1718 | - |
dc.identifier.issn | 1472-779X | - |
dc.identifier.issn | 1364-5471 | - |
dc.identifier.uri | http://hdl.handle.net/2440/4705 | - |
dc.description.abstract | The deacylation of 4-nitrophenyl acetate (pNPA) in aqueous solution to give 4-nitrophenolate is significantly accelerated by the 6A-(ω-aminoalkyl)amino-6A-deoxy-β-cyclodextrins [βCDNH(CH2)nNH2] which are themselves acylated to give predominantly βCDNH(CH2)nNHCOCH3. The deacylation is characterised by kdK = 27.4, 35.5, 24.5 and 16.0 dm3 mol-1 s-1 at 298.2 K in aqueous 0.05 mol dm-3 borate buffer and I = 0.10 mol dm-3 (NaClO4) when n = 2, 3, 4 and 6, respectively, where kd (s-1) is the rate constant for pNPA deacylation through a βCDNH-(CH2)nNH2·pNPA complex characterised by a stability constant K (dm3 mol-1). The inhibition of the deacylation by adamantane-1-carboxylate (AC-) is consistent with a mechanism where AC competes with pNPA in entering the βCDNH(CH2)nNH2 annulus through the formation of a βCDNH(CH2)nNH2·AC- complex. The latter complex has been qualitatively studied by 1H NMR ROESY methods, and its structure and that of βCDNH(CH2)nNH2· pNPA have also been force-field modelled. The possibility of the operation of an SN2 mechanism as an alternative explanation for the deacylation data is also considered. | - |
dc.language.iso | en | - |
dc.publisher | ROYAL SOC CHEMISTRY | - |
dc.source.uri | http://dx.doi.org/10.1039/a902359c | - |
dc.title | Deacylation of 4-nitrophenyl acetate by 6A-(ω-aminoalkyl)amino-6A-deoxy-β-cyclodextrins | - |
dc.title.alternative | Deacylation of 4-nitrophenyl acetate by 6A-(omega-aminoalkyl)amino-6A-deoxy-beta-cyclodextrins | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1039/a902359c | - |
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.