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Matrix isolation and IR spectroscopic characterization of 3,5‐difluoropyridyl‐2,4,6‐trinitrene
Author(s) -
Finke Christopher,
Grote Dirk,
Seidel Rüdiger W.,
Chapyshev Sergei V.,
Sander Wolfram
Publication year - 2012
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1943
Subject(s) - chemistry , electron paramagnetic resonance , matrix isolation , infrared , infrared spectroscopy , characterization (materials science) , density functional theory , irradiation , spectroscopy , photochemistry , matrix (chemical analysis) , ultraviolet , resonance (particle physics) , paramagnetism , analytical chemistry (journal) , nuclear magnetic resonance , computational chemistry , organic chemistry , nanotechnology , atomic physics , optics , materials science , physics , quantum mechanics , chromatography , nuclear physics
The photochemistry of 2,4,6‐triazido‐3,5‐difluoropyridine 21 was investigated by matrix infrared and electron paramagnetic resonance spectroscopies. Ultraviolet irradiation (>260 nm) of 21 results in the formation of 3,5‐difluoropyridyl‐2,4,6‐trinitrene 26 in yields high enough for characterization by infrared spectroscopy. The experimental infrared spectrum is in good agreement with density functional theory calculations. Under similar conditions, a very strong electron paramagnetic resonance spectrum of septet trinitrene 26 was obtained. Shorter irradiation times resulted in more complex product mixtures containing, in addition, mononitrenes and dinitrenes. Surprisingly, azirines and keteneimines, the typical photoproducts of arylnitrenes, were not observed. Copyright © 2011 John Wiley & Sons, Ltd.