An experimental and theoretical study of 1J(13C- 14N) coupling constants in nitro-aromatic and nitro-heteroaromatic compounds

Journal of Molecular Structure

Volumn 979, Issue 1-3, 2010, Pages 180-185

  Jacob, Guy ^a   Hervé, Grégoire ^a   Alkorta, Ibon ^b   Elguero, José ^b  

^a SNPE Materiaux Energetiques   (France)

^b INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

6 311++G(d,p) calculations; 13C 14N couplings; Nitrobenzenes; Nitrofurazans; Nitropyrazoles

Indexed keywords

6-311++G(D,P) CALCULATIONS; 13C-14N COUPLINGS; COUPLING CONSTANTS; DIMENSIONLESS PARAMETERS; HETEROAROMATIC COMPOUNDS; PYRAZOLES; QUADRUPOLES; THEORETICAL STUDY; TORSION ANGLE;

BENZENE; NITROBENZENE;

COUPLINGS;

EID: 77955416893     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2010.06.022     Document Type: Article

References (27)

1. M.-L. Jimeno, I. Alkorta, J. Elguero, and J.E. Del Bene Magn. Reson. Chem. 44 2006 698 707
2. H.-O. Kalinowski, S. Berger, and S. Braun Carbon-13 NMR Spectroscopy 1988 John Wiley and Sons Chichester pp. 569
3. S. Berger, S. Braun, and H.-O. Kalinowski NMR Spectroscopy of the Non-Metallic Elements 1997 John Wiley and Sons Chichester pp. 265
4. M.D. Coburn, C.B. Storm, D.W. Moore, and T.G. Archibald Magn. Reson. Chem. 28 1990 16 20
5. L. Larina, and V. Lopyrev Nitroazoles: Synthesis, Structure and Applications, Topics in Applied Chemistry 2009 Springer Dordrecht pp. 210
6. J.A. Pople Mol. Phys. 1 1958 168 174
7. M. Franck-Neumann, and J.M. Lehn Mol. Phys. 7 1964 197 199
8. M. Suzuki, and R. Kubo Mol. Phys. 7 1964 201 209
9. M. Witanowski, G.A. Webb, Nitrogen NMR spectroscopy, in: E.F. Mooney (Ed.), Ann. Rep. NMR Spectrosc., vol. 5, 1972, pp. 414.
10. A.D. Becke Phys. Rev. A 38 1988 3098 3100
11. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
12. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
13. P.A. Hariharan, and J.A. Pople Theor. Chim. Acta 28 1973 213 222
14. J.W. McIver, and A.K. Komornicki J. Am. Chem. Soc. 94 1972 2625 2633
15. R. Ditchfield, W.J. Hehre, and J.A. Pople J. Chem. Phys. 54 1971 724 728
16. M.J. Frisch, J.A. Pople, R. Krishnam, and J.S. Binkley J. Chem. Phys. 80 1984 3265 3269
17. R. Ditchfield Mol. Phys. 27 1974 789 807
18. F. London J. Phys. Radium 8 1937 397 409
19. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian-03, Revision E01, Gaussian, Inc., Wallingford, CT, 2004.
20. H.-O. Kalinowski, S. Berger, and S. Braun Carbon-13 NMR Spectroscopy 1988 John Wiley and Sons Chichester pp. 315
21. F. Blanco, I. Alkorta, and J. Elguero Magn. Reson. Chem. 45 2007 797 800
22. 15N labeled nitroimidazoles: 2,4-dinitroimidazole (30.6 Hz, 2-nitro); [S. Bulusu, R. Damavarapu, J.R. Autera, B. Behrens, L.M. Minier, J. Villanueva, K. Jayasuriya, T. Axenrod, J. Phys. Chem. 99 (1995) 5009-5015]
23. 15N) values (at the same level than the others compounds of this paper) are: -28.1, -22.9 and -22.8 Hz, that is, about 90% of the experimental ones.
24. L. Ernst, E. Lustig, and V. Wray J. Magn. Reson. 22 1976 459 464
25. G. Hervé, C. Roussel, and H. Graindorge Angew. Chem. Int. Ed. 49 2010 3177 3181
26. C. Roussel, A.T. Balaban, U. Berg, M. Chanon, R. Gallo, G. Klatte, J.A. Memiaghe, J. Metzger, D. Oniciu, and J. Pierrot-Sanders Tetrahedron 39 1983 4209 4219
27. C. Uncuta, I. Paun, C. Deleanu, M. Plavetti, A.T. Balaban, and C. Roussel New J. Chem. 21 1997 1055 1065