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A study of the thermal decomposition of 2-azidoacetamide by ultraviolet photoelectron spectroscopy and matrix-isolation infrared spectroscopy: identification of the imine intermediate H2NCOCHNH

A study of the thermal decomposition of 2-azidoacetamide by ultraviolet photoelectron spectroscopy and matrix-isolation infrared spectroscopy: identification of the imine intermediate H2NCOCHNH
A study of the thermal decomposition of 2-azidoacetamide by ultraviolet photoelectron spectroscopy and matrix-isolation infrared spectroscopy: identification of the imine intermediate H2NCOCHNH
The thermal decomposition of 2-azidoacetamide (N3CH2CONH2) has been studied by matrix-isolation infrared spectroscopy and real-time ultraviolet pbotoelectron spectroscopy. N-2, CH2NH, HNCO, CO, NH3, and HCN are observed as high-temperature decomposition products, while at lower temperatures, the novel imine intermediate H2NCOCH=NH is observed in the matrix-isolation IR experiments. The identity of this intermediate is confirmed both by ab initio molecular orbital calculations of its IR spectrum and by the temperature dependence and distribution of products in the photoelectron spectroscopy (PES) and IR studies. Mechanisms are proposed for the formation and decomposition of the intermediate consistent both with the observed results and with estimated activation energies based on pathway calculations.
gas-phase reactions, vibrational frequencies, 3-membered rings, alkyl azides, pyrolysis, methylenimine, spectrum, acid, polymers
1089-5639
5299-5307
Dyke, J.M.
46393b45-6694-46f3-af20-d7369d26199f
Levita, G.
ef218c00-047c-4ec3-a056-b78237ca2e94
Morris, A.
378f6b9c-92e7-4783-b7be-cafca74b5372
Ogden, J.S.
d022e70d-b424-4100-9517-64a46486dd8c
Dias, A.A.
221a2ab3-3cc5-4635-b9df-bfce6f767364
Algarra, M.
771edccf-5ceb-4186-b7d5-d82468a3177f
Santos, J.P.
2903abeb-2c58-4e5a-8e79-ada8f8bb7251
Costa, M.L.
1dca80c6-c314-453c-b853-382fbeac2770
Rodrigues, P.
0d6b7020-ef36-41c7-aa1a-3d3f259882b4
Barros, M.T.
eee3509f-d7a0-4011-bb00-e4f561fda538
Dyke, J.M.
46393b45-6694-46f3-af20-d7369d26199f
Levita, G.
ef218c00-047c-4ec3-a056-b78237ca2e94
Morris, A.
378f6b9c-92e7-4783-b7be-cafca74b5372
Ogden, J.S.
d022e70d-b424-4100-9517-64a46486dd8c
Dias, A.A.
221a2ab3-3cc5-4635-b9df-bfce6f767364
Algarra, M.
771edccf-5ceb-4186-b7d5-d82468a3177f
Santos, J.P.
2903abeb-2c58-4e5a-8e79-ada8f8bb7251
Costa, M.L.
1dca80c6-c314-453c-b853-382fbeac2770
Rodrigues, P.
0d6b7020-ef36-41c7-aa1a-3d3f259882b4
Barros, M.T.
eee3509f-d7a0-4011-bb00-e4f561fda538

Dyke, J.M., Levita, G., Morris, A., Ogden, J.S., Dias, A.A., Algarra, M., Santos, J.P., Costa, M.L., Rodrigues, P. and Barros, M.T. (2004) A study of the thermal decomposition of 2-azidoacetamide by ultraviolet photoelectron spectroscopy and matrix-isolation infrared spectroscopy: identification of the imine intermediate H2NCOCHNH. Journal of Physical Chemistry A, 108 (25), 5299-5307. (doi:10.1021/jp031288s).

Record type: Article

Abstract

The thermal decomposition of 2-azidoacetamide (N3CH2CONH2) has been studied by matrix-isolation infrared spectroscopy and real-time ultraviolet pbotoelectron spectroscopy. N-2, CH2NH, HNCO, CO, NH3, and HCN are observed as high-temperature decomposition products, while at lower temperatures, the novel imine intermediate H2NCOCH=NH is observed in the matrix-isolation IR experiments. The identity of this intermediate is confirmed both by ab initio molecular orbital calculations of its IR spectrum and by the temperature dependence and distribution of products in the photoelectron spectroscopy (PES) and IR studies. Mechanisms are proposed for the formation and decomposition of the intermediate consistent both with the observed results and with estimated activation energies based on pathway calculations.

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More information

Published date: 24 June 2004
Keywords: gas-phase reactions, vibrational frequencies, 3-membered rings, alkyl azides, pyrolysis, methylenimine, spectrum, acid, polymers

Identifiers

Local EPrints ID: 20189
URI: http://eprints.soton.ac.uk/id/eprint/20189
ISSN: 1089-5639
PURE UUID: 31bc471f-39bd-4281-9b8d-cc3941d4c3d3
ORCID for J.M. Dyke: ORCID iD orcid.org/0000-0002-9808-303X

Catalogue record

Date deposited: 22 Feb 2006
Last modified: 16 Mar 2024 02:36

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Contributors

Author: J.M. Dyke ORCID iD
Author: G. Levita
Author: A. Morris
Author: J.S. Ogden
Author: A.A. Dias
Author: M. Algarra
Author: J.P. Santos
Author: M.L. Costa
Author: P. Rodrigues
Author: M.T. Barros

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