Halide ions complex and deprotonate dipicolinamides and isophthalamides: assessment by mass spectrometry and UV-visible spectroscopy.
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.
Department of Chemistry, Washington University, St. Louis, Missouri 63130, USA.
I Alexandru
IA
Carasel
Carl R
CR
Yamnitz
Rudolph K
RK
Winter
George W
GW
Gokel
D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007477:Ions / Q000737:chemistry*; D013058:Mass Spectrometry; D015394:Molecular Structure; D010648:Phenylacetates / Q000737:chemistry; D010795:Phthalic Acids / Q000737:chemistry*; D010848:Picolinic Acids / Q000737:chemistry*; D011522:Protons; D013056:Spectrophotometry, Ultraviolet
D006846:Hydrocarbons, Halogenated; D007477:Ions; D010648:Phenylacetates; D010795:Phthalic Acids; D010848:Picolinic Acids; D011522:Protons