A laser flash photolysis study of di-, tri- and tetrafluorinated phenylnitrenes; implications for photoaffinity labeling

Several fluorinated aryl azides (2,6 and 2,4-difluorophenyl azide, 2,4,6-triflurorophenyl azide, and methyl 4-azido-2,3,5,6-tetrafluorobenzoate) were studied by laser flash photolysis techniques. In each case, the azides from singlet nitrenes which can be intercepted with pyridine to form ylides. Th...

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Bibliographic Details
Published in:Bioconjugate chemistry 1993-03, Vol.4 (2), p.178-183
Main Authors: Schnapp, Karlyn A, Platz, Matthew S
Format: Article
Language:English
Subjects:
Affinity Labels - chemistry
Azides - chemistry
Fluorine - chemistry
Lasers
Photolysis
Spectrum Analysis
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Summary:Several fluorinated aryl azides (2,6 and 2,4-difluorophenyl azide, 2,4,6-triflurorophenyl azide, and methyl 4-azido-2,3,5,6-tetrafluorobenzoate) were studied by laser flash photolysis techniques. In each case, the azides from singlet nitrenes which can be intercepted with pyridine to form ylides. This allowed determination of the rate constant for ring expansion of the singlet nitrene to the dehydroazepine and measurement of the absolute rate constants for reaction of the singlet nitrenes with typical quenchers.
ISSN:1043-1802
1520-4812
DOI:10.1021/bc00020a011