Thermal decomposition of methyl 2-azidopropionate studied by UV photoelectron spectroscopy and matrix isolation IR spectroscopy: Heterocyclic intermediate vs imine formation

Journal of Physical Chemistry A

Volumn 115, Issue 30, 2011, Pages 8447-8457

  Pinto, R M ^a   Dias, A A ^a   Costa, M L ^a   Rodrigues, P ^b   Barros, M T ^a   Ogden, J S ^c   Dyke, J M ^c  

^a UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^b INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

^c UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DECOMPOSITION PRODUCTS; GASPHASE; IMINE FORMATION; IR SPECTRUM; MATRIX; MATRIX ISOLATION; METHYL FORMATE; PYROLYSIS PROCESS; SPECTRAL SIMULATIONS; SPECTROSCOPIC METHOD; UV PHOTOELECTRON SPECTROSCOPY; VERTICAL IONIZATION ENERGY;

ACTIVATION ANALYSIS; ACTIVATION ENERGY; CARBON DIOXIDE; IONIZATION OF GASES; ISOMERS; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS; PHOTOELECTRICITY; PHOTONS; PYROLYSIS; QUANTUM CHEMISTRY; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL); ULTRAVIOLET PHOTOELECTRON SPECTROSCOPY;

PHOTOELECTRON SPECTROSCOPY;

AZIDE; HETEROCYCLIC COMPOUND; IMINE; METHYL 2 AZIDOPROPIONATE; METHYL 2-AZIDOPROPIONATE; PROPIONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; INFRARED SPECTROPHOTOMETRY; QUANTUM THEORY; SYNTHESIS; THERMODYNAMICS; ULTRAVIOLET RADIATION; X RAY PHOTOELECTRON SPECTROSCOPY;

AZIDES; HETEROCYCLIC COMPOUNDS; IMINES; MODELS, MOLECULAR; PHOTOELECTRON SPECTROSCOPY; PROPIONATES; QUANTUM THEORY; SPECTROPHOTOMETRY, INFRARED; THERMODYNAMICS; ULTRAVIOLET RAYS;

EID: 79960922187     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp2036845     Document Type: Article

References (32)

1. Patai, S. The chemistry of the azido group; Chemistry of functional groups; Interscience Publishers: New York, 1971.
2. Bräse, S.; Banert, K. Organic Azides: Syntheses and Applications; John Wiley & Sons: New York, 2009.
3. Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188-5240
4. Bock, H.; Dammel, R. Angew. Chem., Int. Ed. 1987, 26, 504-526
5. Nguyen, M. T.; Sengupta, D.; Ha, T.-K. J. Phys. Chem. 1996, 100, 6499-6503
6. Dyke, J. M.; Levita, G.; Morris, A.; Ogden, J. S.; Dias, A. A.; Algarra, M.; Santos, J. P.; Costa, M. L.; Rodrigues, P.; Barros, M. T. J. Phys. Chem. A 2004, 108, 5299-5307
7. Dyke, J. M.; Levita, G.; Morris, A.; Ogden, J. S.; Dias, A. A.; Algarra, M.; Santos, J. P.; Costa, M. L.; Rodrigues, P.; Andrade, M. M.; Barros, M. T. Chem.-Eur. J. 2005, 11, 1665-1676
8. Hooper, N.; Beeching, L. J.; Dyke, J. M.; Morris, A.; Ogden, J. S.; Dias, A. A.; Costa, M. L.; Barros, M. T.; Cabral, M. H.; Moutinho, A. M. C. J. Phys. Chem. A 2002, 106, 9968-9975
9. O'Keeffe, P.; Scotti, G.; Stranges, D.; Rodrigues, P.; Barros, M. T.; Costa, M. L. J. Phys. Chem. A 2008, 112, 3086-3093
10. Dyke, J. M.; Groves, A. P.; Morris, A.; Ogden, J. S.; Catarino, M. I.; Dias, A. A.; Oliveira, A. M. S.; Costa, M. L.; Barros, M. T.; Cabral, M. H.; Moutinho, A. M. C. J. Phys. Chem. A 1999, 103, 8239-8245
11. Dyke, J. M.; Groves, A. P.; Morris, A.; Ogden, J. S.; Dias, A. A.; Oliveira, A. M. S.; Costa, M. L.; Barros, M. T.; Cabral, M. H.; Moutinho, A. M. C. J. Am. Chem. Soc. 1997, 119, 6883-6887
12. Pinto, R. M.; Dias, A. A.; Costa, M. L. J. Mol. Struct.: THEOCHEM 2009, 894, 80-87
13. Morris, A.; Jonathan, N.; Dyke, J. M.; Francis, P. D.; Keddar, N.; Mills, J. D. Rev. Sci. Instrum. 1984, 55, 172-181
14. Kimura, K. Handbook of HeI photoelectron spectra of fundamental organic molecules: ionization energies, ab initio assignments, and valence electronic structure for 200 molecules; Japan Scientific Societies Press; Halsted Press: Tokyo; New York, 1981.
15. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618-622
16. Parr, R.; Weitao, Y. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1994.
17. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654
18. Cederbaum, L. S. J. Phys. B 1975, 8, 290
19. von Niessen, W.; Schirmer, J.; Cederbaum, L. S. Comput. Phys. Rep. 1984, 1, 57-125
20. Ortiz, J. V. J. Chem. Phys. 1996, 104, 7599-7605
21. Zaytseva, I. L.; Trofimov, A. B.; Schirmer, J.; Plekan, O.; Feyer, V.; Richter, R.; Coreno, M.; Prince, K. C. J. Phys. Chem. A 2009, 113, 15142-15149
22. Trofimov, A. B.; Schirmer, J.; Kobychev, V. B.; Potts, A. W.; Holland, D. M. P.; Karlsson, L. J. Phys. B 2006, 39, 305
23. Chrostowska, A.; Nguyen, T. X. M.; Dargelos, A.; Khayar, S.; Graciaa, A.; Guillemin, J. J. Phys. Chem. A 2009, 113, 2387-2396
24. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1998, 109, 7764-7776
25. Potts, A. W.; Holland, D. M. P.; Trofimov, A. B.; Schirmer, J.; Karlsson, L.; Siegbahn, K. J. Phys. B 2003, 36, 3129
26. Andersson, M. P.; Uvdal, P. J. Phys. Chem. A 2005, 109, 2937-2941
27. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas,.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision A.02.; Gaussian Inc.: Wallingford CT, 2009.
28. Nunes, Y.; Martins, G.; Mason, N. J.; Duflot, D.; Hoffmann, S. V.; Delwiche, J.; Hubin-Franskin, M.-J.; Limão-Vieira, P. Phys. Chem. Chem. Phys. 2010, 12, 15734-15743
29. Francisco, J. S. J. Am. Chem. Soc. 2003, 125, 10475-10480
30. Metcalfe, W. K.; Simmie, J. M.; Curran, H. J. J. Phys. Chem. A 2010, 114, 5478-5484
31. Arenas, J. F.; Marcos, J. I.; López-Tocón, I.; Otero, J. C.; Soto, J. J. Chem. Phys. 2000, 113, 2282-2289
32. Sheppard, W. A. J. Org. Chem. 1962, 27, 3756-3759