A probable hydrogen-bonded meisenheimer complex: An unusually high S NAr reactivity of nitroaniline derivatives with hydroxide ion in aqueous media

Journal of Organic Chemistry

Volumn 76, Issue 15, 2011, Pages 6356-6361

  Imoto, Mitsutaka ^a   Matsui, Yasunori ^b   Takeda, Motonori ^a   Tamaki, Akihiro ^a   Taniguchi, Hisaji ^a,b   Mizuno, Kazuhiko ^b,c   Ikeda, Hiroshi ^b,c  

^a Seika Corporation   (Japan)

^b Graduate School of Engineering   (Japan)

^c Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4-NITROPHENOL; AQUEOUS MEDIA; DENSITY FUNCTIONAL THEORY CALCULATIONS; HYDROGEN BONDING INTERACTIONS; HYDROXIDE IONS; LEAVING GROUPS; NITROANILINES; NITROPHENOLS; SIX-MEMBERED RINGS;

DENSITY FUNCTIONAL THEORY; HYDROGEN; HYDROGEN BONDS; NITROGEN COMPOUNDS; ORGANIC SOLVENTS; PHENOLS;

ANILINE;

1 CHLORO 4 NITROBENZENE; 4 NITROANILINE; 4 NITROPHENOL; CHLORINE; CHLOROBENZENE; HYDROXIDE; WATER;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; HYDROGEN BOND; HYDROPHOBICITY; MEISENHEIMER COMPLEX; SOLUBILITY; SUBSTITUTION REACTION;

EID: 79961054503     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2007219     Document Type: Article

References (24)

1. Bunnet, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273-412
2. Miller, J. Aromatic Nucleophilic Substitution; Elsevier: New York, 1969.
3. Terrier, F. Nucleophilic Aromatic Displacement. The Influence of the Nitro Group; VCH: New York, 1991.
4. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structures; McGraw-Hill: New York, 1968; p 498.
5. Hojo, M.; Masuda, R.; Okada, E.; Miya, H. Synthesis 1989, 870-873
6. Hlavac, J.; Soural, M.; Hradil, P.; Frysova, I.; Slouka, J. J. Heterocycl. Chem. 2004, 41, 633-636
7. Mitchell, A. R.; Coburn, M. D.; Lee, G. S.; Schmidt, R. D.; Pagoria, P. F.; Hsu, P. C. U.S. Patent 70, 743, 2005
8. Chem. Abstr. 2005, 142, 336118.
9. Baltas, M.; Cazaux, L.; Blic, A. D.; Gorrichon, L.; Tisnes, P. J. Chem. Res., Synop. 1988, 284-285
10. Kesten, S. J.; Johnson, J.; Werbel, L. M. J. Med. Chem. 1987, 30, 906-911
11. Belov, A. V.; Nichvoloda, V. M. Russ. J. Org. Chem. 2005, 41, 124-127
12. Ji, P.; Atherton, J. H.; Page, M. I. J. Org. Chem. 2011, 76, 3286-3295
13. Imoto, M.; Takeda, M.; Tamaki, A.; Taniguchi, H.; Mizuno, K. Org. Prep. Proced. Int. 2010, 42, 161-167
14. Rossi, R. H.; Vargas, E. B. J. Am. Chem. Soc. 1981, 103, 1533-1540
15. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
16. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
17. Dunning, T. H. J. Chem. Phys. 1989, 90, 1007-1023
18. Frisch, M. J. Gaussian 98, revision A.11.4; Gaussian, Inc.: Pittsburgh, PA, 1998.
19. Figure 1 was drawn by using WinMOPAC ver 3.9; Stewart, J. J. P; Fujitsu Ltd.: Japan, 2004.
20. The Merck Index, 12 th ed.; Budavari, S., Ed.; Merck Research Laboratories: NJ, 1996.
21. Wegscheider, R.; Klemenc, A. Monatsh. Chem. 1910, 709-743
22. Meldola, R.; Stephens, F. G. C. J. Chem. Soc. 1906, 924-928
23. Cornelis, A.; Laszlo, P.; Pennetreau, P. Bull. Soc. Chim. Belg. 1984, 93, 961-972
24. Handbook of Fine Chemicals; Sigma-Aldrich Chemical Co.: St. Louis, MO, 2009-2010.