Anion receptors based on 4-nitrophenylhydrazone. Issue 29 (20th July 2016)

• Record Type: Journal Article
• Authors: Jo, Jaeyoung; Putikam, Raghunath; Lin, M.C.; Kang, Jongmin
• Is Part Of: Tetrahedron letters. Volume 57:Issue 29(2016)
• Page Start: 3208
• Page End: 3214
• Publication Date: 2016-07-20
• Subjects: Anion receptor -- Hydrazone -- C–H hydrogen bond; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.06.041
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Anion receptors utilizing hydrazone N–H and C–H hydrogen bonds have been designed. Receptor1 showed affinities for dihydrogen phosphate and acetate. Receptor2 showed relatively strong affinities for dihydrogen phosphate. The binding modes of these receptors are shown from modeling studies. Abstract: We have designed and synthesized new chromogenic anion receptors1 and2, which utilized 4-nitrophenylhydrazone as anion recognition moiety. UV–vis and 1 H NMR titration showed that receptors1 and2 bound anions utilizing two hydrazone N–H hydrogen bond and two C–H hydrogen bond. Despite the weak hydrogen bonding abilities of binding motifs, receptor1 showed affinities for dihydrogen phosphate and acetate and receptor2 showed relatively strong affinities for dihydrogen phosphate in polar solvent such as 5% DMSO in CH3 CN.