2-(3,5-Dinitrophenyl)-1,3-dithiane carbanion: A benzylic anion with a low energy triplet state

Journal of the American Chemical Society

Volumn 133, Issue 39, 2011, Pages 15553-15558

  Perrotta, Raffaele R ^a   Winter, Arthur H ^b   Coldren, William H ^a   Falvey, Daniel E ^b  

^a Bldg 142   (United States)

^b IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIC; CHEMICAL TRAPPING; DFT LEVELS; DIRADICALS; ELECTRON WITHDRAWING GROUP; LITHIUM IONS; LOW ENERGIES; META POSITIONS; SINGLET-TRIPLET ENERGY GAP; TRIPLET ELECTRONIC STATE; TRIPLET STATE;

GROUND STATE; LITHIUM;

NEGATIVE IONS;

1,3 DITHIANE DERIVATIVE; 2 (3,5 DINITROPHENYL) 1,3 DITHIANE; ANION; BENZILIC ACID; LITHIUM ION; UNCLASSIFIED DRUG;

ARTICLE; DENSITY FUNCTIONAL THEORY; ELECTRON; ENERGY; ORGANIC CHEMISTRY; PREDICTION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 80053294965     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja204711a     Document Type: Article

References (69)

1. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
2. Perdew, J. P.; Yue, W. Phys. Rev. B. 1996, 33, 8800-8802
3. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
4. Krylov, A. I. Acc. Chem. Res. 2006, 39, 83-91
5. Bally, T.; Borden, W. T. Rev. Comput. Chem. 1999, 13, 1-97
6. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
7. Poutsma, J. C.; Upshaw, S. D.; Squires, R. R.; Wenthold, P. G. J. Phys. Chem. A 2002, 106, 1067-1073
8. Cramer, C. J. J. Am. Chem. Soc. 1999, 120, 6261-6269
9. Andersson, K.; Malmqvist, P. A.; Ross, B. O. J. Chem. Phys. 1992, 96, 1218-1226
10. Ess, D. H.; Johnson, E. R.; Hu, X. Q.; Yang, W. T. J. Phys. Chem. A 2011, 115, 76-83
11. Wright, B. B.; Platz, M. S. J. Am. Chem. Soc. 1983, 105, 628-630
12. Lahti, P. M. Magnetic Properties Of Organic Materials; Marcel Dekker: New York, 1999.
13. Borden, W. T. Diradicals; Wiley: New York, 1982.
14. Nozawa, T.; Nagata, M.; Ichinohe, M.; Sekiguchi, A. J. Am. Chem. Soc. 2011, 133, 5773-5775
15. Shil, S.; Misra, A. J. Phys. Chem. A 2010, 114, 2022-2027
16. Shultz, D. A.; Fico, R. M.; Bodner, S. H.; Kumar, R. K.; Vostrikove, K. E.; Kampf, J. W.; Boyle, P. D. J. Am. Chem. Soc. 2003, 125, 11761-11771
17. Oka, H. Org. Lett. 2010, 12, 448-451
18. Rajca, A.; Wongsriratanakul, J.; Rajca, S. Science 2001, 294, 1503-1505
19. Lochmann, L.; Bauer, W. J. Am. Chem. Soc. 1992, 114, 7482-7489
20. Wenthold, P. G.; Kim, J. B.; Lineberger, W. C. J. Am. Chem. Soc. 1997, 119, 1354-1359
21. Neuaus, P.; Grotte, D.; Sander, W. J. Am. Chem. Soc. 2008, 130, 2993-3000
22. Wang, T.; Krylov, A. I. J. Chem. Phys. 2005, 123, 6
23. Lenington, M. J.; Wenthold, P. G. J. Phys. Chem. A 2010, 114, 1334-1337
24. Rajca, A.; Olankitanit, A.; Rajca, S. J. Am. Chem. Soc. 2011, 133, 4750-4753
25. Nemirowski, A.; Schreiner, P. R. J. Org. Chem. 2007, 72, 9533-9540
26. Wang, J.; Kubicki, J.; Peng, H.; Platz, M. S. J. Am. Chem. Soc. 2008, 130, 6604-6609
27. Woddcock, H. L.; Moran, D.; Brooks, B. R.; Schleyer, P. V.; Schaefer, H. F. J. Am. Chem. Soc. 2007, 129, 3763-3770
28. Hirai, K.; Itoh, T.; Tomioka, H. Chem. Rev. 2009, 109, 3275-3332
29. Tomioka, H.; Nakane, N.; Tatsugi, J. Bull. Chem. Soc. Jpn. 2008, 81, 1629-1637
30. Tomioka, H.; Moss, R. A.; Platz, M. S.; Jones, M., Jr. Triplet Carbenes in Reactive Intermediate Chemistry; John Wiley and Sons: Hoboken, NJ, 2004; pp 375-462.
31. Dougherty, D. A. Acc. Chem. Res. 1991, 24, 88-94
32. Gilroy, J. B.; McKinnon, S. D.; Kennepohl, P.; Zsombor, M. S.; Ferguson, M. J.; Thompson, L. K.; Hicks, R. G. J. Org. Chem. 2007, 72, 8062-8069
33. Fukuzaki, E.; Nishide, H. Org. Lett. 2006, 8, 1835-1838
34. Lee, E. C.; Choi, Y. C.; Kim, W. Y.; Singh, N. J.; Lee, S.; Shim, J. H.; Kim, K. S. Chem.-Eur. J. 2010, 16, 12141-12146
35. Rajca, A. Advances in Physical Organic Chemistry; Elsevier Academic Press, Inc.: San Diego, CA, 2005; Vol. 40, pp 153-199.
36. Ichino, T.; Vilano, S. M.; Gianola, A. J.; Goebbert, D. J.; Velarde, L.; Sanov, A.; Blanksby, S. J.; Zhou, X.; Hrovat, D. A.; Borden, W. T.; Lineberger, W. C. Angew. Chem., Int. Ed. 2009, 48, 8509-8511
37. Amiri, S.; Schreiner, P. R. J. Phys. Chem. A 2009, 113, 11750-11757
38. Hirai, K.; Itoh, T.; Tomioka, H. Chem. Rev. 2009, 109, 3275-3332
39. Winter, A. H.; Falvey, D. E.; Cramer, C. J. J. Am. Chem. Soc. 2004, 126, 9661-9668
40. Perrotta, R. R.; Winter, A. H.; Falvey, D. E. Org. Lett. 2011, 13, 212-215
41. Winter, A. H.; Falvey, D. E. J. Am. Chem. Soc. 2010, 132, 215-222
42. Corey, E. J.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1965, 4, 1075-1077
43. Corey, E. J.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1965, 4, 1077-1078
44. Corey, E. J.; Seebach, D. J. Org. Chem. 1966, 31, 4097-4099
45. Seebach, D.; Jones, N. R.; Corey, E. J. J. Org. Chem. 1968, 33, 300-305
46. Seebach, D.; Corey, E. J. Org. Synth. 1968, 50, 72
47. Seebach, D.; Corey, E. J. J. Org. Chem. 1975, 40, 231-237
48. Stowell, M. H. B.; Rock, R. S.; Rees, D. C.; Chan, S. I. Tetrahedron Lett. 1996, 37, 307-310
49. Hassan, H. H. A. M.; Tamm, C. Helv. Chim. Acta 1996, 79, 518-526
50. Lee, H. B.; Balasubramian, S. J. Org. Chem. 1999, 64, 3454-3460
51. Bräuer, M.; Weston, J.; Anders, E. J. Org. Chem. 2000, 65, 1193-1199
52. Eliel, E. L.; Abatjoglou, A. G.; Kuyper, L. F. J. Am. Chem. Soc. 1977, 99, 8262-8269
53. Gunther, H. J. Braz. Chem. Soc. 1999, 10, 241, general example of anions in proton NMR behavior
54. Carlin, R. L. Magnetochemistry; Springer: Heidelberg, Germany, 1986; pp 5-18.
55. Dowd, P. J. Am. Chem. Soc. 1966, 88, 2587
56. Dowd, P. Acc. Chem. Res. 1972, 5
57. Burns, G. J. Appl. Phys. 1961, 32, 2048
58. Wertz, J. E.; Bolton, J. R. Electron Spin Resonance Elementary Theory and Practical Application; McGraw-Hill: New York, 1972; Chapter 10.
59. Wasserman, E.; Snyder, L. C.; Yager, W. A. J. Chem. Phys. 1964, 41, 1763
60. Gordy, W. In Theory and Applications of Electron Spin Resoance; West, W., Ed.; John Wiley and Sons, Inc.: New York, 1980, Vol. 15, p 589 (A Weissberger series ed.).
61. Loliger, J.; Schefford, R. J. Chem. Educ. 1972, 49, 646-647
62. Ostfeld, D.; Cohen, A. J. Chem. Educ. 1972, 49, 829
63. Piguet, C. J. Chem. Educ. 1997, 74, 815-816
64. Crawford, T. H.; Swanson, J. J. Chem. Educ. 1971, 48, 382-386
65. Grant, D. H. J. Chem. Educ. 1995, 72, 39-40
66. Schubert, E. M. J. Chem. Educ. 1992, 69, 62
67. Cu, A.; Testa, A. C. J. Am. Chem. Soc. 1974, 96, 1963-1965
68. Banik, B. K.; Mukhopadhyay, C.; Venkatraman, M. S.; Becker, F. F. Tetrahedron Lett. 1998, 39, 7243-7246
69. Ankner, T.; Hilmersson, G. Tetrahedron Lett. 2007, 48, 5707-5710