Kinetics and thermodynamics of amine and diamine signaling by a trifluoroacetyl azobenzene reporter group.
[reaction: see text] (Trifluoroacetyl)azobenzene dyes were previously employed as amine reporter groups (chemosensors) in a dendrimer-based monomolecular imprinting system. Kinetic and binding studies with a range of amines and diamines show that the highly selective signaling observed for alkane diamines by these imprinted dendrimers arises from a kinetic effect due to intramolecular general base-catalyzed carbinolamine formation with the dye itself. The relationship between diamine structure and carbinolamine stability and rate of formation is described.
Mertz
Eric
E
Department of Chemistry, 600 S. Matthews Ave, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.
Beil
James B
JB
Zimmerman
Steven C
SC
D000588:Amines / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D003959:Diamines / Q000737:chemistry*; D019281:Dimerization; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure; D013053:Spectrophotometry / Q000379:methods; D013816:Thermodynamics
D000588:Amines; D001391:Azo Compounds; D003959:Diamines; D006845:Hydrocarbons, Fluorinated; C009850:azobenzene