Thermal isomerization of acetylnitrene: A quantum-chemical study

Russian Chemical Bulletin

Volumn 52, Issue 11, 2003, Pages 2328-2333

  Faustov, V I ^a   Baskir, E G ^a   Biryukov, A A ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Acetylnitrene; B3lyp density functional; Curtius rearrangement; Formylnitrene; G2(MP2,SVP) computational scheme; Quantum chemical calculations

Indexed keywords

ACETYLNITRENE; AZIDE; CARBONYL DERIVATIVE; FORMYLNITRENE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; DECOMPOSITION; GEOMETRY; ISOMERIZATION; MATHEMATICAL ANALYSIS; QUANTUM CHEMISTRY; THERMAL ANALYSIS; THERMODYNAMICS;

EID: 3543082168     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:RUCB.0000012352.44860.39     Document Type: Article

References (29)

1. T. Curtius, Ber., 1890, 23, 3023.
2. Nitrenes, Ed. W. Lwowski, Wiley, New York, 1970.
3. W. Lwowski, in Azides and Nitrenes, Ed. E. F. V. Scriven, Acad. Press, New York, 1984, Ch. 4.
4. W. Lwowski, R. DcMauriac, T. W. Mattingly, and E. Scheiffele, Tetrahedron Lett., 1964, 3285.
5. J. H. Teles and G. Maier, Chem. Ber., 1989, 122, 745.
6. T. Autrey and G. B. Schuster, J. Am. Chem. Soc., 1987, 109, 58148.
7. D. Poppinger, L. Radom, and J. A. Pople, J. Am. Chem. Soc., 1977, 99, 7806.
8. K. Yokayama, S.-Y. Takane, and T. Fueno, Bull. Chem. Soc. Jpn., 1991, 64, 2230.
9. A. M. Mebel, A. Luna, M. C. Lin, and K. Morokuma, J. Chem. Phys., 1996, 105, 6439.
10. W. A. Shapley and G. B. Bacskay, J. Phys. Chem., A, 1999, 103, 6625.
11. W. A. Shapley and G. B. Bacskay, J. Phys. Chem., A, 1999, 103, 4514.
12. P. A. S. Smith, in Organic Reactions 3, Wiley, 1944, Ch. 9, p. 337.
13. Organic Syntheses, Collection 2, Ed. A. Blatt, Queens College Fluoshing, New York, 1946.
14. J. F. Sullivan, H. L. Heusel, W. M. Zunic, J. R. Durig, and S. Cradock, Spectrochim. Acta, Part A: Molecular and Biomolecular Spectroscopy, 1994, 50, 435.
15. J. Koput, Chem. Phys. Lett., 1995, 242, 514.
16. T. Pasinszki and N. P. C. Westwood, J. Phys. Chem., 1995, 99, 1649.
17. P. Babinec and J. Leszczynski, J. Mol. Structure (Theochem), 2000, 501, 277.
18. S. Okumoto and S. Yamabe, J. Org. Chem., 1999, 64, 4742.
19. A. D. Becke, J. Chem. Phys., 1993, 98, 5648.
20. L. A. Curtiss, P. C. Redfern, B. J. Smith, and L. Radom, J. Chem. Phys., 1996, 104, 5148.
21. L. A. Curtiss, K. Raghavachari, G. W. Trucks, and J. A. Pople, J. Chem. Phys., 1991, 94, 7221.
22. R. J. Scott and L. Radom, J. Phys. Chem., 1996, 100, 16502.
23. J. B. Foresman and A. Frisch, Exploring Chemistry with Electronic Structure Methods, 2nd ed., Gaussian, Inc., Pittsburgh (PA, 15106 USA), 1998.
24. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, GAUSSIAN 98, Revision A.7, Gaussian, Inc., Pittsburgh (PA), 1998.
25. J. Koput, J. Mol. Spectroscopy, 1986, 115, 131.
26. T. Sakaizumi, M. Namikawa, and O. Ohashi, J. Mol. Structure, 1995, 345, 189.
27. N. P. Gritsan and E. A. Pritchina, Mendeleev Commun., 2001, 11, 94.
28. E. T. Denisov, Kinetika gomogennykh khimicheskikh reaktsij [The Kinetics of Homogeneous Chemical Reactions], Vysshaya Shkola, Moscow, 1978, 83 pp. (in Russian).
29. K. Jensen, M. Due, and A. Holm, Acta Chem. Scand., 1965, 19, 438.