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4-Amino-1,8-naphthalimide-based anion receptors: employing the naphthalimide N-H moiety in the cooperative binding of dihydrogenphosphate
journal contribution
posted on 2005-09-19, 00:00 authored by Fred PfefferFred Pfeffer, A Buschgens, Neil BarnettNeil Barnett, T Gunnlaugsson, P KrugerThe 4-amino-1,8-naphthalimide-based anion receptor 3 binds dihydrogenphosphate with 1:1 stoichiometry through cooperative hydrogen bonding to a naphthalimide N–H and thiourea N–H groups. This was clearly established from 1H NMR titration experiments in DMSO-d6 where a substantial shift in the resonance for the naphthalimide N–H was observed concomitant with the expected thiourea N–H chemical shift migration upon successive additions of H2PO4−. However, whilst 1H NMR titration experiments indicate that 3 was capable of binding other anions such as acetate, the naphthalimide N–H does not participate and the N–H resonance was essentially invariant during the titration. The lack of cooperative binding in this instance was justifiable on steric grounds.
History
Journal
Tetrahedron lettersVolume
46Issue
38Pagination
6579 - 6584Publisher
ElsevierLocation
Amsterdam, The NetherlandsPublisher DOI
ISSN
0040-4039eISSN
1873-3581Language
engNotes
Available online 9 August 2005.Publication classification
C1 Refereed article in a scholarly journalCopyright notice
2005, ElsevierUsage metrics
Keywords
supramolecular chemistryanion recognitionhydrogen bondinganionsacetatedihydrogenphosphateScience & TechnologyPhysical SciencesChemistry, OrganicChemistryPHOTOINDUCED ELECTRON-TRANSFERCHARGE NEUTRAL THIOUREAPET SENSORSBIS-CARBOXYLATESCYCLEN COMPLEXESRECOGNITIONCHEMOSENSORSPYROPHOSPHATEDEPROTONATIONHIGHLIGHTSOrganic Chemistry
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