Ab initio and NBO studies of the decomposition ([2+2] and [2+4]elimination) mechanisms of alkylisothiocyanates (alkyl = ethyl-, iso-propyl- and tert-butyl)

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 181, Issue 1, 2006, Pages 75-85

  Nori Shargh, Davood ^a,b   Abbasi, Atyeh ^a   Jameh Bozorghi, Saeed ^a   Deyhimi, Farzad ^c   Naeem Abyaneh, Reza ^a   Sarkar, Fatemeh ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b ISLAMIC AZAD UNIVERSITY   (Iran)

^c SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

Ab initio; Decomposition; Isothiocyanate; Molecular modeling; Natural bond orbital

Indexed keywords

EID: 29244484506     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/104265090968983     Document Type: Article

References (23)

1. N. Barroeta and A. Maccoll, J. Chem. Soc. (B), 347 (1969).
2. N. Barroeta and M. Umana, Acta Clent. Venet., 26, 67 (1975).
3. F. W. Schneider and B. S. Rabinovitch, J. Am. Chem. Soc., 85, 2365 (1963).
4. J. Casanova, N. D. Werner, and R. E. Shuster, J. Org. Chem., 31, 3473 (1966).
5. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrazewski, J. A. Montgomery, Jr., R. E. Startmann, 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. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui. K. Morokuma, D. K. Malik, A. D. Rabuck, K. Raghavachar, J. B. Foresman, J. Cioslowski, J. V. Ortiz, 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. Nanyakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, and J. A. Pople, GAUSSIAN 98 (Revision A3), Gaussian Inc, Pittsburgh, PA, 1998).
6. A. D. Becke, J. Chem. Phys., 98, 5648 (1993).
7. C. Lee, W. Yang, and R. C. Parr, Phys. Rev. B., 37, 785 (1988).
8. W. J. Hehri, L. Radom, P. V. R. Schleyer, and J. A. Pople, Ab Initio Molecular Orbital Theory (Wiley, New York, 1986).
9. J. M. Seminarino and P. Politzer, Eds., Modern Density Functional Theory, A Tool for Chemistry (Elsevier, Amsterdam, 1995).
10. A. E. Reed, L. A. Curtiss, and F. Weinhold, Chem. Rev., 88, 899 (1988).
11. J. P. Foster and F. Weinhold, J. Am. Chem. Soc., 102, 7211 (1980).
12. A. E. Reed and F. Weinhold, J. Chem. Phys., 83, 1736 (1985).
13. E. D. Glendening, A. E. Reed, J. E. Carpenter, and F. Weinhold, Natural Bond Orbital (Version 3.1) Madison, Wisconsin, USA.
14. Serena Software, Bloomington, IN, USA.
15. J. J. P. Stewart, QCPE 581, Department of Chemistry, Indiana University, Bloomington, IN, USA.
16. (a) J. W. McIver, Jr, Acc. Chem. Res., 7, 72 (1974);
17. (b) O. Ermer, Tetrahedron, 31, 1849 (1975).
18. M. J. S. Dewar, E. F. Heally, and J. J. P. Stewart, J. Chem. Soc. Faraday. Trans., 80, 227 (1984).
19. F. Freeman, A. Phornvoranunt, and W. J. Hehre, J. Phys. Org. Chem., 11, 831 (1998).
20. T. M. Gilbert, Tetrahedron Lett., 39, 9147 (1998).
21. M. Remko, P. D. Lyne, and W. G. Richards, Phys. Chem. Chem. Phys., 1, 5353 (1999).
22. A. D. Strickland and R. A. Caldwell, J. Phys. Chem., 97, 13394 (1993).
23. I. Arnason, G. K. Thorarinsson, and E. Matern, J. Mol. Struct. (Theochem), 91, 454 (1998).