Abstract
The chiral chemosensor 1, based on a thiourea-activated phthalimide, is available by four reaction steps from 4-nitrophthalimide. 1 detects fluoride, chloride, acetate, and dihydrogen phosphate anions by changes in UV-vis absorption. Fluoride in excess induces deprotonation whereas the other anions show only complex formation in the ground state. (1)H-NMR studies confirm the formation of these H-bonded complexes and the fluoride-induced receptor deprotonation in the recognition process. Moderate chiral recognition was observed for sodium D/L-lactate with K(ass)(D)/K(ass)(L) = 1.93.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Anions / chemistry*
-
Carboxylic Acids / chemistry*
-
Colorimetry / methods*
-
Kinetics
-
Magnetic Resonance Spectroscopy
-
Nitro Compounds / chemistry*
-
Phthalimides / chemical synthesis
-
Phthalimides / chemistry*
-
Sodium Lactate / chemistry
-
Spectrophotometry, Ultraviolet
-
Stereoisomerism
-
Thiourea / analogs & derivatives*
-
Thiourea / chemical synthesis
-
Thiourea / chemistry*
Substances
-
1-(2-benzyl-1,3-dioxoisoindolin-5-yl)-3-(1-phenylethyl)thiourea
-
Anions
-
Carboxylic Acids
-
Nitro Compounds
-
Phthalimides
-
4-nitrophthalimide
-
Thiourea
-
Sodium Lactate