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4-Amino-1,8-naphthalimide-based anion receptors: employing the naphthalimide N-H moiety in the cooperative binding of dihydrogenphosphate

Pfeffer, Frederick, Buschgens, Alisha, Barnett, Neil, Gunnlaugsson, Thorfinnur and Kruger, Paul 2005, 4-Amino-1,8-naphthalimide-based anion receptors: employing the naphthalimide N-H moiety in the cooperative binding of dihydrogenphosphate, Tetrahedron letters, vol. 46, no. 38, pp. 6579-6584.

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Title 4-Amino-1,8-naphthalimide-based anion receptors: employing the naphthalimide N-H moiety in the cooperative binding of dihydrogenphosphate
Author(s) Pfeffer, Frederick
Buschgens, Alisha
Barnett, Neil
Gunnlaugsson, Thorfinnur
Kruger, Paul
Journal name Tetrahedron letters
Volume number 46
Issue number 38
Start page 6579
End page 6584
Publisher Elsevier Ltd
Place of publication Amsterdam, The Netherlands
Publication date 2005-09-19
ISSN 0040-4039
1873-3581
Keyword(s) supramolecular chemistry
anion recognition
hydrogen bonding
anions
acetate
dihydrogenphosphate
Summary The 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.
Notes Available online 9 August 2005.
Language eng
Field of Research 030302 Nanochemistry and Supramolecular Chemistry
HERDC Research category C1 Refereed article in a scholarly journal
Copyright notice ©2005, Elsevier Ltd
Persistent URL http://hdl.handle.net/10536/DRO/DU:30003197

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