Computational studies of ion pairing. 7. Ion-pairing and association effects between tetraalkylammonium ions and nitrobenzene redox species. "ion pairing" to neutral substances

Journal of Organic Chemistry

Volumn 78, Issue 5, 2013, Pages 2111-2117

  Fry, Albert J ^a  

^a WESLEYAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; COMPUTATION THEORY; MOLECULAR OXYGEN; NITROBENZENE; POSITIVE IONS; SUPRAMOLECULAR CHEMISTRY;

AMMONIUM CATIONS; ANION RADICALS; COMPUTATIONAL STUDIES; DEGREE OF CERTAINTY; HYDROGEN ATOMS; MOLECULAR PAIRS; REDOX SPECIES; TETRAALKYLAMMONIUM;

DENSITY FUNCTIONAL THEORY;

ACETONITRILE; AMMONIA; CATION; HYDROGEN; NITROBENZENE; NITROGEN; OXYGEN;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; ENERGY; MOLECULAR RECOGNITION; SUPRAMOLECULAR CHEMISTRY;

EID: 84874591715     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302385r     Document Type: Article

References (38)

1. Fry, A. J. Phys. Chem. Chem. Phys. 2010, 12, 14775
2. Fry, A. J.; Steffen, L. K. J. Electroanal. Chem. 2010, 638, 218
3. Fry, A. J. Electrochem. Commun. 2009, 11, 309
4. Fry, A. J. Electroanalysis 2006, 18, 379
5. Fry, A. J. Tetrahedron 2006, 62, 6558
6. Fry, A. J. Electrochem. Commun. 2005, 7, 602
7. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 3 rd ed.; Wiley-VCH: Weinheim, 2011.
8. Zuccaccia, C.; Stahl, N. G.; Macchioni, A.; Chen, M.-C.; Roberts, J. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 1448
9. Macchioni, A. Eur. J. Inorg. Chem. 2003, 195
10. Zuccaccia, C.; Bellachioma, G.; Cardaci, G.; Macchioni, A. J. Am. Chem. Soc. 2001, 123, 11020
11. Hill, H. A. O.; Roberts, R. G.; Williams, D.; Zarb-Adami, N. J. Chem. Soc., Faraday Trans. 2 1976, 72, 1267
12. Bertini, I.; Kursula, P.; Luchinat, C.; Parigi, G.; Vahokoski, J.; Wilmanns, M.; Yuan, J. J. Am. Chem. Soc. 2009, 131, 5134
13. Simonetta, M. Int. Rev. Phys. Chem. 1981, 1, 31 (b).
14. Kong, J.; Schleyer, P. v. R.; Rzaepa, H. S. J. Org. Chem. 2010, 75, 5164
15. Ali-Torres, J.; Marechal, J.-D.; Rodriguez-Santiago, L.; Sodupe, M. J. Am. Chem. Soc. 2011, 133, 15008
16. Dixon, D. D.; Tius, M. A.; Pratt, L. M. J. Org. Chem. 2009, 74, 5881
17. Szczecinski, P.; Gryff-Keller, A.; Molchanov, S. J. Org. Chem. 2006, 71, 4636
18. Cordaro, J. G.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 16192
19. Barbosa, F.; Peron, V.; Gescheidt, G.; Furstner, A. J. Org. Chem. 1998, 63, 8806
20. Jensen, B. S.; Parker, V. D. J. Am. Chem. Soc. 1975, 97, 5211
21. Fry, A. J.; Hutchins, C. S.; Chung, L. L. J. Am. Chem. Soc. 1975, 97, 591
22. Fry, A. J. In The Chemistry of Amino, Nitroso, Nitro, and Related Groups; Patai, S., Ed.; Wiley: New York, 1996; Chapter 18, pp 827-855.
23. Fry, A. J. J. Electroanal. Chem. 2003, 546, 35
24. Gaussian 09, Revision A.02: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.;; Fox, D. J. Gaussian, Inc., Wallingford, CT, 2009.
25. Leach, A. R. Molecular Modeling:Principles and Applications; Prentice-Hall: Englewood Cliffs, New Jersey, 2001.
26. Chengteh Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
27. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027
28. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999
29. Benson, S. W. The Foundations of Chemical Kinetics; McGraw-Hill: New York, 1960; pp 565-568.
30. Bailey, W. F.; Monahan, A. S. J. Chem. Educ. 1978, 55, 489 (see p 491).
31. Schlag, E. W. J. Chem. Phys. 1965, 42, 584
32. Alder, R. W.; Allen, P. R.; Anderson, K. R.; Butts, C. P.; Khosravi, E.; Martin, A.; Maunder, C. M.; Orpen, A. G.; Pourcain, C. P. S. J. Chem. Soc. Perkin Trans. 2. 1998, 2083
33. Luzhkov, V. B.; Oesterberg, F.; Acharya, P.; Chattopadhyaya, J.; Aqvist, J. Phys. Chem. Chem. Phys. 2002, 4, 4640
34. Wait, E.; Powell, H. H. J. Chem.Soc. 1958, 1872
35. Pradines, V.; Poteau, R.; Pimienta, V. Chem. Phys. Chem. 2007, 8, 1524
36. Arunan, E.; Gutowsky, H. S. J. Chem. Phys. 1993, 98, 4294
37. Fry, A. J. Tetrahedron 2008, 64, 2101-2103
38. Maki, A. H.; Geske, D. H. J. Am. Chem. Soc. 1961, 83, 1853