Synthesis, characterization, and electrochemical studies of PPh 3-n(dipp)n (dipp = 2,6-diisopropylphenyl): Steric and electronic effects on the chemical and electrochemical oxidation of a homologous series of triarylphosphines and the reactivities of the corresponding phosphoniumyl radical cations

Journal of the American Chemical Society

Volumn 135, Issue 30, 2013, Pages 11205-11215

  Bullock, John P ^a   Bond, Alan M ^b   Boeré, René T ^c   Gietz, Twyla M ^c   Roemmele, Tracey L ^c   Seagrave, Sonja D ^c   Masuda, Jason D ^d   Parvez, Masood ^e  

^a BENNINGTON COLLEGE   (United States)

^b MONASH UNIVERSITY   (Australia)

^c UNIVERSITY OF LETHBRIDGE   (Canada)

^d SAINT MARY S UNIVERSITY   (Canada)

^e UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION BARRIERS; CRYSTALLOGRAPHIC CHARACTERIZATION; ELECTROCHEMICAL STUDIES; ELECTRON TRANSFER PROCESS; HETEROGENEOUS ELECTRON TRANSFER; REORGANIZATIONAL ENERGY; STERIC REQUIREMENTS; SYNTHETIC STRATEGIES;

ELECTROCHEMICAL OXIDATION; ELECTRON TRANSITIONS;

FREE RADICAL REACTIONS;

CATION; FREE RADICAL; GRIGNARD REAGENT; HYDROXYL RADICAL; PHOSPHINE DERIVATIVE; PHOSPHONIUM DERIVATIVE;

ALKYLATION; ARTICLE; CONTROLLED STUDY; CYCLIC POTENTIOMETRY; ELECTRIC POTENTIAL; ELECTROCHEMISTRY; ELECTRON TRANSPORT; KINETICS; OXIDATION REDUCTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84881048052     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja403555d     Document Type: Article

References (66)

1. Dostrovsky, I.; Hughes, E. D.; Ingold, C. K. J. Chem. Soc. 1946, 173-194
2. Basolo, F.; Chatt, J.; Gray, H. B.; Pearson, R. G.; Shaw, B. L. J. Chem. Soc. 1961, 2207-2215
3. Brown, H. C.; Sclesinger, H. I.; Cardon, S. Z. J. Am. Chem. Soc. 1942, 64, 325-329
4. Griller, D.; Ingold, K. U. Acc. Chem. Res. 1976, 9, 13-19
5. Hubig, S. M.; Rathore, R.; Kochi, J. K. J. Am. Chem. Soc. 1999, 121, 617-626
6. Bond, A. M.; Duffy, N. W.; Guo, S.-X.; Zhang, J.; Elton, D. M. Anal. Chem. 2005, 77, 186A-195A
7. Fischer, R. C.; Power, P. P. Chem. Rev. 2010, 110, 3877-3923
8. Power, P. P. Chem. Rev. 1999, 99, 3463-3503
9. Li, L.; Fukawa, T.; Matsuo, T.; Hashizume, D.; Fueno, H.; Tanaka, K.; Tamao, K. Nat. Chem. 2012, 4, 361-365
10. Power, P. P. Nat. Chem. 2012, 4, 343-344
11. Wang, Y.; Quillian, B.; Wei, P.; Wannere, C. S.; Xie, Y.; King, R. B.; Schaefer, H. F.; Schleyer, P. V.; Robinson, G. H. J. Am. Chem. Soc. 2007, 129, 12412-12413
12. Wang, Y. Z.; Xie, Y. M.; Wei, P. R.; King, R. B.; Schaefer, H. F.; Schleyer, P. V.; Robinson, G. H. Science 2008, 321, 1069-1071
13. Wang, Y. Z.; Xie, Y. M.; Wei, P. R.; King, R. B.; Schaefer, H. F.; Schleyer, P. V.; Robinson, G. H. J. Am. Chem. Soc. 2008, 130, 14970-14971
14. Kinjo, R.; Donnadieu, B.; Celik, M. A.; Frenking, G.; Bertrand, G. Science 2011, 333, 610-613
15. Valente, C.; Calimsiz, S.; Hoi, K. H.; Mallik, D.; Sayah, M.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 3314-3332
16. Balogh, J.; Slawin, A. M. Z.; Nolan, S. P. Organometallics 2012, 31, 3259-3263
17. Rekken, B. D.; Brown, T. M.; Fettinger, J. C.; Tuononen, H. M.; Power, P. P. J. Am. Chem. Soc. 2012, 134, 6504-6507
18. Summerscales, O. T.; Olmstead, M. M.; Power, P. P. Organometallics 2011, 30, 3468-3471
19. Woodul, W. D.; Carter, E.; Müller, R.; Richards, A. F.; Stasch, A.; Kaupp, M.; Murphy, D. M.; Driess, M.; Jones, C. J. Am. Chem. Soc. 2011, 133, 10074-10077
20. Sheberla, D.; Tumanskii, B.; Bravo-Zhivotovskii, D.; Molev, G.; Molev, V.; Lee, V. Y.; Takanashi, K.; Sekiguchi, A.; Apeloig, Y. Organometallics 2010, 29, 5596 - 5606
21. Ishida, S.; Hirakawa, F.; Iwamoto, T. J. Am. Chem. Soc. 2011, 133, 12968-12971.
22. Pan, X.; Chen, X.; Li, T.; Li, Y.; Wang, X. J. Am. Chem. Soc. 2013, 135, 3414-3417
23. Pan, X.; Su, Y.; Chen, X.; Li, Y.; Zuo, J.; Wang, X. J. Am. Chem. Soc. 2013, 135, 5561-5564
24. Protasiewicz, J. D.; Washington, M. P.; Gudimetla, V. B.; Payton, J. L.; Simpson, M. C. Inorg. Chim. Acta 2010, 364, 39-45
25. Dutan, C.; Shah, S.; Smith, R. C.; Choua, S.; Berclaz, T.; Geoffroy, M.; Protasiewicz, J. D. Inorg. Chem. 2003, 42, 6241-6251
26. Smith, R. C.; Gleason, L. B.; Protasiewicz, J. D. J. Mater. Chem. 2006, 16, 2445-2452
27. Smith, R. C.; Ren, T.; Protasiewicz, J. D. Eur. J. Inorg. Chem. 2002, 2779-2783
28. Smith, R. C.; Shah, S.; Urnezius, E.; Protasiewicz, J. D. J. Am. Chem. Soc. 2003, 125, 40-41
29. Stephan, D. W. Org. Biomol. Chem. 2008, 6, 1535-1539
30. Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46-76
31. Ménard, G.; Hatnean, J. A.; Cowley, H. J.; Lough, A. J.; Rawson, J. M.; Stephan, D. W. J. Am. Chem. Soc. 2013, 135, 6446-6449
32. Boeré, R. T.; Bond, A. M.; Cronin, S.; Duffy, N. W.; Hazendonk, P.; Masuda, J. D.; Pollard, K.; Roemmele, T. L.; Tran, P.; Zhang, Y. New J. Chem. 2008, 32, 214-231
33. Boeré, R. T.; Masuda, J. D.; Tran, P. J. Organomet. Chem. 2006, 691, 5585-5591
34. Sasaki, S.; Yoshifuji, M. Curr. Org. Chem 2007, 11, 17-31
35. Changenet, P.; Plaza, P.; Martin, M. M.; Meyer, J. Y.; Rettig, W. Chem. Phys. 1997, 221, 311-322
36. Rozanel'skaya, N. A.; Bokanov, A. I.; Uzhinov, B. M.; Stepanov, B. I. J. Gen. Chem. USSR 1975, 45, 277-280
37. Bryce, D. L.; Eichele, K.; Wasylishen, R. E. Inorg. Chem. 2003, 42, 5085-5096
38. Schiavon, G.; Zercchin, S.; Cogoni, G.; Bontempelli, G. J. Electroanal. Chem. 1973, 48, 425-431
39. Ohmori, H.; Nakai, S.; Masui, M. J. Chem. Soc., Perkin Trans. 1 1978, 1333-1335
40. Culcasi, M.; Berchadsky, Y.; Gronchi, G.; Tordo, P. J. Org. Chem. 1991, 56, 3537-3542
41. Tordo, P. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed., Wiley: Chichester, 1990; Vol. 1, Chapter 6.
42. Sasaki, S.; Sutoh, K.; Murakami, M.; Yoshifuji, M. J. Am. Chem. Soc. 2002, 124, 14830-14831
43. Sasaki, S.; Chowdhury, R.; Yoshifuji, M. Tetrahedron Lett. 2004, 45, 9193-9196
44. Merzougui, B.; Berchadsky, Y.; Tordo, P.; Gronchi, G. Electrochim. Acta 1997, 42, 2445-2453
45. Zagumennov, V. A.; Nikitin, E. V. Russ. J. Electrochem. 2003, 39, 1236-1239
46. Palau, C.; Berchadsky, Y.; Chalier, F.; Finet, J.-P.; Gronchi, G.; Tordo, P. J. Phys. Chem. 1995, 99, 158-163
47. Caram, J. A.; Vasini, E. J. Electrochim. Acta 1994, 39, 2395-2400
48. Bond, A. M.; Duffy, N. W.; Elton, D. M.; Fleming, B. D. Anal. Chem. 2009, 81, 8801-8808
49. Zhang, J.; Guo, S.-X.; Bond, A. M. Anal. Chem. 2007, 79, 2276-2288
50. Sher, A. A.; Bond, A. M.; Gavaghan, D. J.; Harriman, K.; Feldberg, S. W.; Duffy, N. W.; Guo, S.-X.; Zhang J. Anal. Chem. 2004, 76, 6214-6228
51. Zhang, J.; Guo, S.-X.; Bond, A. M. Anal. Chem. 2007, 79, 2276-2288
52. O'Mullane, A. P.; Zhang, J.; Brajter-Toth, A.; Bond, A. M. Anal. Chem. 2008, 80, 4614-4626
53. Guo, S.; Zhang, J.; Elton, D. M.; Bond, A. M. Anal. Chem. 2004, 76, 166-177
54. Fleming, B. D.; Barlow, N. L.; Zhang, J.; Bond, A. M.; Armstrong, F. A. Anal. Chem. 2006, 78, 2948-2956
55. Lee, C. Y.; Fleming, B. D.; Zhang, J.; Guo, S.-X.; Elton, D. M.; Bond, A. M. Anal. Chim. Acta 2009, 652, 205-214
56. Fleming, B. D.; Zhang, J.; Elton, D. M.; Bond, A. M. Anal. Chem. 2007, 79, 6516-6526
57. Lertanantawong, B.; O'Mullane, A. P.; Zhang, J.; Surareungchai, W.; Somasudrum, M.; Bond, A. M. Anal. Chem. 2008, 80, 6515-6525
58. Lee, C.-Y.; Bullock, J. P.; Kennedy, G. F.; Bond, A. M. J. Phys. Chem. A 2010, 114, 10122-10134
59. Bullock, J. P.; Mashkina, E.; Bond, A. M. J. Phys. Chem. A 2011, 115, 6493-6502
60. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications, 2 nd ed.; Wiley: New York, 2001; Chapter 5.
61. Gennett, T.; Milner, D. F.; Weaver, M. J. J. Phys. Chem. 1985, 89, 2787-2794
62. Marcus, R. A. J. Chem. Phys. 1965, 43, 679-701
63. Richardson, J. N.; Harvey, J.; Murray, R. W. J. Phys. Chem. 1994, 98, 13396-13402
64. Fawcett, W. R.; Opallo, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2131-2143
65. Bott, R. C.; Bowmaker, G. A.; Buckley, R. W.; Healy, P. C.; Perera, M. C. S. Aust. J. Chem. 2000, 53, 175-181
66. Blount, J. F.; Camp, D.; Hart, R. D.; Healy, P. C.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1994, 47, 1631-1639