Halide Ions Complex and Deprotonate Dipicolinamides and Isophthalamides: Assessment by Mass Spectrometry and UV−Visible Spectroscopy

Abstract

The F(-), Cl(-), and Br(-) binding selectivity of bis(p-nitroanilide)s of dipicolinic and isophthalic acids was studied by using competitive electrospray mass spectrometry and UV-Visible spectroscopy. Both hosts prefer binding Cl(-) over either F(-) or Br(-). Host deprotonation was observed to some extent in all experiments in which the host was exposed to halide ions. When F(-) was present, host deprotonation was often the major process, whereas little deprotonation was observed by Cl(-) or Br(-), which preferred complexation. A solution of either host changed color when mixed with a F(-), H(2)PO(4)(-), di- or triphenylacetate solution.

Sensitive water-soluble fluorescent chemosensor for chloride based on a bisquinolinium pyridine-dicarboxamide compound

“…The binding constant calculated for chloride from fluorescence data is unexpectedly high K A(Cl -) = 5050 M -1 probably due to the exciplex formation. As noted in previous works, this pyridine-2,6-dicarboxamide fragment often has high affinity and selectivity for chloride (Carasel et al, 2010;Dorazco-González et al, 2010;Hancock et al, 2010;Wenzel et al, 2012). From these data, the order of affinity of 1 for anions is F -<< Cl ->> H 2 P 2 O 7 2-> CH 3 CO 2 -> Br -> I -and the effect of quenching is Cl -~ I -> Br ->> F -and oxoanions.…”

Photoinduced triplet-state electron transfer of platinum porphyrin: a one-step direct method for sensing iodide with an unprecedented detection limit

“…[12][13][14] In addition to its environmental and biological importance, iodide is a key component of a redox couple oen used in solar-energyharvesting systems. 15 Various methods can be used for the determination of iodide, 16 including photoluminescence, [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32] colorimetric detection, [33][34][35][36][37] time-resolved absorption techniques, 38 mass spectrometry, [39][40][41] chromatography, 42 Raman scattering 43,44 and electrochemical proling. 45,46 However, because of its large size and weakly basic nature, the binding capacity of iodide is the weakest among the halide ions.…”

Chromogenic and fluorogenic chemosensors and reagents for anions. A comprehensive review of the years 2010–2011

“…7). 22 Titration of 16 with F -in CH 3 CO 2 CH 2 CH 3 resulted firstly in the diminished absorbance of the maximum at 322 nm (due to the formation of 1:1 coordination complexes), followed by a shift of the maximum absorption from 322 to 343 nm (due to deprotonation in the presence of excess F -). Moreover in the presence of Cl -or Br -, complexation was preferred.…”