On the causes of potential inversion in 1,2,4,5-tetrakis(amino)benzenes

Journal of Organic Chemistry

Volumn 75, Issue 4, 2010, Pages 1168-1178

  Adams, Christopher J ^a   Da Costa, Rosenildo C ^a   Edge, Ruth ^b   Evans, Dennis H ^c   Hood, Matthew F ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

^c PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTALLOGRAPHIC CHARACTERIZATION; DFT STUDY; DICATIONS; ION PAIRING; OXIDIZING AGENTS; RADICAL CATIONS; RADICAL SALTS; TETRAKIS;

BENZENE; IONS; SALTS;

CYCLIC VOLTAMMETRY;

3,6 DIFLUORO 1,2,4,5 TETRAKIS(AMINO)BENZENE; ANILINE DERIVATIVE; BENZENE DERIVATIVE; ELECTROLYTE; MORPHOLINE DERIVATIVE; PIPERIDINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY DIFFRACTION;

EID: 77249168191     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902411b     Document Type: Article

References (34)

1. Michaelis, L. Chem. Rev. 1935, 16, 243-286.
2. Elbl, K.; Krieger, C.; Staab, H. A. Angew. Chem., Int. Ed. Engl. 1986, 25, 1023-1024.
3. Dähne, S.; Leupold, D. Angew. Chem., Int. Ed. Engl. 1966, 5, 984-993.
4. Braunstein, P.; Siri, O.; Taquet, J.-P.; Rohmer, M.-M.; Bénard, M.; Welter, R. J. Am. Chem. Soc. 2003, 125, 12246-12256.
5. Siri, O.; Braunstein, P.; Rohmer, M.-M.; Bénard, M.; Welter, R. J. Am. Chem. Soc. 2003, 125, 13793-13803.
6. Sorokin, V. I.; Ozeryanskii, V. A.; Borodkin, G. S. Synthesis 2006, 97-102.
7. Sorokin, V. I.; Ozeryanskii, V. A.; Borodkin, G. S.; Chernyshev, A. V.; Muir, M.; Baker, J. Z. Naturforsch. 2006, 61b, 615-625.
8. Wenderski, T.; Light, K. M.; Ogrin, D.; Bott, S. G.; Harlan, C. J. Tetrahedron Lett. 2004, 45, 6851-6853.
9. Khramov, D. M.; Boydston, A. J.; Bielawski, C. W. Org. Lett. 2006, 8, 1831-1834.
10. Witulski, B.; Senft, S.; Thum, A. Synlett 1998, 504-506.
11. Evans, D. H. Chem. Rev. 2008, 108, 2113-2144.
12. Elbl-Weiser, K.; Neugebauer, F. A.; Staab, H. A. Tetrahedron Lett. 1989, 30, 6161-6164.
13. Nafady, A.; Chin, T. T.; Geiger, W. E. Organometallics 2006, 25, 1654-1663.
14. Hill, M. G.; Lamanna, W. M.; Mann, K. R. Inorg. Chem. 1991, 30, 4687-4690.
15. Bancroft, E. E.; Pemberton, J. E.; Blount, H. N. J. Phys. Chem. 1980, 84, 2557-2560.
16. Barrière, F.; Geiger, W. E. J. Am .Chem. Soc 2006, 128, 3980-3989.
17. Bock, H.; Ruppert, K.;Näther, C.; Havlas, Z. Angew. Chem., Int. Ed. Engl. 1991, 30, 1180-1183.
18. Speiser, B.;Würde, M.; Maichle-Mössmer, C. Chem.; Eur. J. 1998, 4, 222-233.
19. Barth, T.; Neugebauer, F. A. J. Org. Chem. 1995, 60, 5401-5406.
20. Fry, A. J. Electroanalysis 2006, 18, 391-398.
21. Macías-Ruvalcaba, N. A.; Evans, D. H. J. Phys. Chem. B 2005, 109, 14642-14647.
22. Taube, R.; Wache, S. J. Organomet. Chem. 1992, 428, 431-442.
23. Chávez, I.; Alvarez-Carena, A.; Molins, E.; Roig, A.; Maniukiewicz, W.; Arancibia, A.; Arancibia, V.; Brand, H.; Manuel Manríquez, J. J. Organomet. Chem. 2000, 601, 126-132.
24. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877-910.
25. Chavez, I.; Alvarez-Carena, A.; Molins, E.; Roig, A.; Maniukiewicz, W.; Arancibia, A.; Arancibia, V.; Brand, H.; Manriquez, J. M. J. Organomet. Chem. 2000, 601, 126-132.
26. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112-122.
27. Müller, P. Cryst. Rev. 2009, 15, 57-83.
28. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.04; Gaussian, Inc.: Wallingford, CT, 2003.
29. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
30. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
31. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211.
32. Cossi, M.; Barone, V. J. Chem. Phys. 2001, 115, 4708-4717.
33. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43-54.
34. Ochterski, J. W. Thermochemistry in Gaussian; Gaussian, Inc.: Wallingford, CT, 2000.