Protonated nitro group: Structure, energy and conjugation

Organic and Biomolecular Chemistry

Volumn 3, Issue 10, 2005, Pages 1838-1843

  Exner, Otto ^a   Böhm, Stanislav ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CONFORMATIONS; DERIVATIVES; METHANE; ORGANIC SOLVENTS; RESONANCE;

INTERACTION ENERGY; ISODESMIC REACTIONS; NITROMETHANE; PROTONATION;

NITROGEN COMPOUNDS;

EID: 19944370557     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b502152a     Document Type: Article

References (45)

1. E. P. L. Hunter and S. G. Lias, J. Phys. Chem. Ref. Data, 1998, 27, 413-656.
2. M. Liler, J. Chem. Soc., 1962, 4272-4282;
3. J. C. D. Brand, J. C. Horning and M. B. Thornley, J. Chem. Soc., 1952, 1374-1383;
4. R. J. Gillespie, T. E. Peel and E. A. Robinson, J. Am. Chem. Soc., 1971, 93, 5083-5087.
5. E. Rolli and R. Houriet, Spectrosc. Int. J., 1984, 3, 177-183.
6. M. Taagepera, K. D. Summerhays, W. J. Hehre, R. D. Topsom, A. Press, L. Radom and R. W. Taft, J. Org. Chem., 1981, 46, 891-903.
7. P.-C. Maria, I. Leito, J.-F. Gal, O. Exner and M. Decouzon, Bull. Soc. Chim. Fr., 1995, 132, 394-401.
8. O. Exner and S. Böhm, Phys. Chem. Chem. Phys., 2004, 6, 3864-3871.
9. M. Decouzon, O. Exner, J.-F. Gal and P.-C. Maria, J. Phys. Org. Chem., 1994, 7, 615-624.
10. O. Castaño, R. Notario, K. Hori and J.-L. M. Abboud, Struct. Chem., 1996, 7, 321-327.
11. M. R. Siggel and T. D. Thomas, J. Am. Chem. Soc., 1986, 108, 4360-4363;
12. K. B. Wiberg, J. Ochterski and A. Streitwieser Jr., J. Am. Chem. Soc., 1996, 118, 8291-8299.
13. M. J. S. Dewar and K. L. Krull J. Chem. Soc., Chem. Commun., 1990, 333-334;
14. R. W. Taft, I. A. Koppel, R. D. Topsom and F. Anvia, J. Am. Chem. Soc., 1990, 112, 2047-2052;
15. C. L. Perrin, J. Am. Chem. Soc., 1991, 113, 2865-2868;
16. P. Burk and P. v. R. Schleyer, J. Mol. Struct. (Theochem.), 2000, 505, 161-167;
17. P. R. Rablen, J. Am. Chem. Soc., 2000, 122, 357-368;
18. J. Holt and J. M. Karty, J. Am. Chem. Soc., 2003, 125, 2797-2803.
19. O. Exner, J. Org. Chem., 1988, 53, 1812-1815;
20. O. Exner and P.Čársky, J. Am. Chem. Soc., 2001, 123, 9564-9570.
21. S. Böhm and O. Exner, New J. Chem., 2005, 29, 336-342.
22. O. Exner and S. Böhm, J. Org. Chem., 2002, 67, 6320-6327.
23. A. Pross, L. Radom and R. W. Taft, J. Org. Chem., 1980, 45, 818-826;
24. O. Exner, Org. Reactivity (Tartu), 1995, 29, 1-6.
25. (a) L. P. Hammett, Physical Organic Chemistry, McGraw-Hill, New York, 2nd edn., 1970, ch. 11.9;
26. (b) O. Exner, Correlation Analysis of Chemical Data, Plenum Press, New York, 1988, ch. 2.
27. 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 and J. A. Pople, Gaussian 03, Revision B.03, Gaussian, Inc., Pittsburgh, PA, 2003.
28. M. L. Senent, Mol. Phys., 2001, 99, 1311-1321.
29. O. Exner and S. Böhm, Collect. Czech. Chem. Commun., 2001, 66, 1623-1637.
30. P. George, M. Trachtman, C. W. Bock and A. M. Brett, J. Chem. Soc., Perkin Trans. 2, 1976, 1222-1227.
31. E. M. S. Maçôas, L. Khriachtchev, M. Pettersson, R. Fausto and M. Räsänen, J. Am. Chem. Soc., 2003, 125, 16 188-16 189.
32. O. Exner, in The Chemistry of Functional Groups, Supplement A3: The Chemistry of Double-Bonded Functional Groups, S. Patai, ed., Wiley, New York, 1997, pp. 261-307 and refs. cited therein.
33. M. Ludwig, S. Wold and O. Exner, Acta Chem. Scand, 1992, 46, 549-554.
34. C. Mansch, A. Leo and R. W. Taft, Chem. Rev., 1991, 91, 165-195.
35. M. Sjöström and S. Wold, Chem. Str., 1976, 9, 200-210.
36. R. W. Taft, J. Phys. Chem., 1960, 64, 1805-1815;
37. S. Ehrenson, R. T. C. Brownlee and R. W. Taft, Prog. Phys. Org. Chem., 1973, 10, 1-80.
38. M. Charton, Prog. Phys. Org. Chem., 1981, 13, 119-251.
39. Ref. 15h, pp. 124-125.
40. K. Palát Jr, S. Böhm, G. Braunerová, K. Waisser and O. Exner, New J. Chem., 2002, 26, 861-866.
41. P. C. Hiberty and G. Ohanessian, J. Am. Chem. Soc., 1984, 106, 6963-6968;
42. T. M. Krygowski and J. Maurin, J. Chem. Soc., Perkin Trans. 2, 1989, 695-698.
43. S. Irle, T. M. Krygowski, J. E. Niu and W. H. E. Schwarz, J. Org. Chem., 1995, 60, 6744-6755.
44. S. D. Kahn, W. J. Hehre and J. A. Pople, J. Am. Chem. Soc., 1987, 109, 1871-1873.
45. O. Exner, J. Phys. Org. Chem., 1990, 3, 190-194.