Attempted Isolation, Spectroscopic Characterization, and Computational Study of Diazirinone (N2CO), its Analogs, and their Precursors

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Scientific paper

Intrigued by the 2005 reported synthesis of diazirinone, we carried out further experimental and theoretical studies aimed at the detailed matrix-isolation and millimeter-wave spectroscopic characterizations. Diazirinone is a peculiar isoconjugate of two very stable molecules, CO and N2, which may be of astrochemical interest. Unfortunately, the previous reported methods of diazirinone generation did not yield this species, but rather its decomposition products. Encouraged by the many computational studies of the N2CO potential energy surface that all found diazirinone to be the lowest energy isomer, save its decomposition products, we proposed a new method of preparation of diazirinone from the photolysis or thermolysis of carbonyl diazide by loss of two nitrogen molecules.
We were able to generate the highly explosive carbonyl diazide in sufficient yield from the reaction of triphosgene and sodium azide. This has allowed us to obtain a matrix-isolation and gas phase IR spectrum of carbonyl diazide which has a gas-phase lifetime of several days. We are currently engaged in the safe purification and distillation of our sample and obtaining a millimeter-wave spectrum of carbonyl diazide. We will attempt to photolyze or thermolyze this molecule to release diazirinone and characterize it by millimeter-wave spectroscopy to pave the way for possible astrochemical detection.
In order to provide better mechanistic insight into the decomposition of carbonyl diazide to diazirinone, we have engaged in a DFT and ab initio computational study of several possible pathways. Our preliminary results suggest that of the pathways studied, a step-wise process in which an acyclic CON4 species is generated by loss of nitrogen followed by possible rearrangement and further loss of N2 is most likely. These results will be compared to the analogous reactions for azirinone (HC2NO), our next likely synthetic and spectroscopic target.
The millimeter-wave absorption spectrometer used in this research project has been used previously for the investigation of numerous small inorganic molecules and ions. The apparatus consists of a three-meter Pyrex discharge chamber with cylindrical electrodes at each end. The discharge operates at mTorr pressures and at temperatures as low as 77 K. The microwave signal is generated by a Gunn-diode microwave source, which is then further amplified and multiplied to reach the desired frequencies. The signal is focused onto a liquid-helium-cooled indium antimonide detector.

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