2-Azidoacetic acid
(N3CH2CO2H) has been
synthesized and characterized by a variety of
spectroscopic
techniques, and the thermal decomposition of this molecule studied by
matrix isolation infrared spectroscopy and
real-time ultraviolet photoelectron spectroscopy. The results are
consistent with the vapor phase thermal decomposition
following a pathway involving concerted ejection of molecular
N2 and the simultaneous formation of CO2
and
methanimine (CH2NH). No evidence was found for
the presence of intermediates such as the nitrene
NCH2CO2H
or the imine HNCHCO2H. At higher temperatures,
CH2NH further decomposes to give HCN and
H2.
2-Azidoacetone (N3CH2COCH3) has been synthesized and characterized by a variety of spectroscopic
techniques, and the thermal decomposition of this molecule at temperatures in the region 300−1150 K has
been studied by matrix isolation infrared spectroscopy and real-time ultraviolet photoelectron spectroscopy.
The results show the effectively simultaneous production of six prominent decomposition products: CH2NH,
CH2CO, HCN, CO, N2, and CH3CHO, and several reaction pathways are proposed to account for their
formation. Results of ab initio molecular orbital calculations indicate that the primary reaction intermediate
is the imine HNCHCOCH3, with the nitrene NCH2COCH3 being a transition state. No experimental evidence
was found for the presence of the imine HNCHCOCH3, but mechanistic considerations, and the existence of
several weak unassigned IR bands point to the presence of a further decomposition product, which may be
CH2NCH3.
He I photoelectron spectra have been recorded for the F + C 2 H 5 OH reaction, and a band has been identified associated with the primary reaction product CH 3 CHOH. The first adiabatic and vertical ionization energies of this radical have been measured as (6.64 ( 0.03) and ( 7.29 ( 0.03) eV respectively. The assignment of this band to CH 3 CHOH is supported by ab initio calculations performed at the G2 level of theory. Spectra recorded at different reaction times have demonstrated the short-lived nature of CH 3 CHOH and the major pathway of the F + C 2 H 5 OH reaction. The value measured for the adiabatic ionization energy has allowed the heat of formation of CH 3 CHOH to be derived from the heat of formation of CH 3 CHOH + .
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