NMR and computational studies of the configurational properties of spirodioxyselenuranes. Are dynamic exchange processes or temperature-dependent chemical shifts involved?

Journal of Organic Chemistry

Volumn 77, Issue 20, 2012, Pages 9268-9276

  Press, David J ^a   McNeil, Nicole M R ^a   Rauk, Arvi ^a   Back, Thomas G ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACID CATALYST; BENZYLIC; C-O CLEAVAGE; COMPUTATIONAL INVESTIGATION; COMPUTATIONAL STUDIES; EXCHANGE PROCESS; HIGH ACTIVATION ENERGY; INTERMEDIATE TEMPERATURES; LOW TEMPERATURES; LOW-ACTIVATION ENERGY; PRESENCE OF WATER; PSEUDOROTATION; STEREOMUTATIONS; TEMPERATURE DEPENDENCE; TEMPERATURE DEPENDENT; VARIABLE-TEMPERATURE NMR;

ACTIVATION ENERGY; COALESCENCE; HYDROGEN; PROTONS; SELENIUM; TEMPERATURE DISTRIBUTION;

CHEMICAL SHIFT;

ACID; CARBENE; HYDROGEN; SELENIUM; SOLVENT; SPIRO COMPOUND; SPIRODIOXYSELENURANE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYST; CHEMICAL BOND; DIASTEREOISOMER; ENERGY; HEATING; LOW TEMPERATURE; MOLECULAR DYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANOSELENIUM COMPOUNDS; QUANTUM THEORY; SPIRO COMPOUNDS; TEMPERATURE;

EID: 84867697704     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301846a     Document Type: Article

References (87)

1. Back, T. G.; Moussa, Z. J. Am. Chem. Soc. 2002, 124, 12104-12105
2. Back, T. G.; Moussa, Z. J. Am. Chem. Soc. 2003, 125, 13455-13460
3. Back, T. G.; Moussa, Z.; Parvez, M. Angew. Chem., Int. Ed. 2004, 43, 1268-1270
4. Mugesh, G.; du Mont, W.-W.; Sies, H. Chem. Rev. 2001, 101, 2125-2179
5. Mugesh, G.; Singh, H. B. Chem. Soc. Rev. 2000, 29, 347-357
6. Mugesh, G.; du Mont, W.-W. Chem.-Eur. J. 2001, 7, 1365-1370
7. Bhabak, K. P.; Mugesh, G. Acc. Chem. Res. 2010, 43, 1408-1419
8. Epp, O.; Ladenstein, R.; Wendel, A. Eur. J. Biochem. 1983, 133, 51-69
9. Ganther, H. E. Chem. Scr. 1975, 8a, 79-84
10. Ganther, H. E.; Kraus, R. J. In Methods in Enzymology; Colowick, S. P.; Kaplan, N. O., Eds.; Academic Press: New York, 1984; Vol. 107, pp 593-602.
11. Stadtman, T. C. J. Biol. Chem. 1991, 266, 16257-16260
12. Tappel, A. L. Curr. Top. Cell. Regul. 1984, 24, 87-97
13. Flohé, L. Curr. Top. Cell. Regul. 1985, 27, 473-478
14. Nogueira, C. W.; Zeni, G.; Rocha, J. B. T. Chem. Rev. 2004, 104, 6255-6286
15. Back, T. G.; Kuzma, D.; Parvez, M. J. Org. Chem. 2005, 70, 9230-9236
16. Press, D. J.; Mercier, E. A.; Kuzma, D.; Back, T. G. J. Org. Chem. 2008, 73, 4252-4255
17. Tripathi, S. K.; Patel, U.; Roy, D.; Sunoj, R. B.; Singh, H. B.; Wolmershäuser, G.; Butcher, R. J. J. Org. Chem. 2005, 70, 9237-9247
18. Tripathi, S. K.; Sharma, S.; Singh, H. B.; Butcher, R. J. Org. Biomol. Chem. 2011, 9, 581-587
19. Kuzma, D.; Parvez, M.; Back, T. G. Org. Biomol. Chem. 2007, 5, 3213-3217
20. Sarma, B. K.; Manna, D.; Minoura, M.; Mugesh, G. J. Am. Chem. Soc. 2010, 132, 5364-5374
21. Selvakumar, K.; Singh, H. B.; Goel, N.; Singh, U. P.; Butcher, R. J. Dalton Trans. 2011, 40, 9858-9867
22. Selvakumar, K.; Singh, H. B.; Goel, N.; Singh, U. P.; Butcher, R. J. Chem.-Eur. J. 2012, 18, 1444-1457
23. Drabowicz, J.; Halaba, G. Rev. Heteroat. Chem. 2000, 22, 1-32
24. Allenmark, S. Chirality 2008, 20, 544-551
25. Claeson, S.; Langer, V.; Allenmark, S. Chirality 2000, 12, 71-75
26. Drabowicz, J.; Luczak, J.; Mikolajczyk, M.; Yamamoto, Y.; Matsukawa, S.; Akiba, K. Tetrahedron: Asymmetry 2002, 13, 2079-2082
27. Drabowicz, J.; Luczak, J.; Mikolajczyk, M.; Yamamoto, Y.; Matsukawa, S.; Akiba, K. Chirality 2004, 16, 598-601
28. Petrovic, A. G.; Polavarapu, P. L.; Drabowicz, J.; Zhang, Y.; McConnell, O. J.; Duddeck, H. Chem.-Eur. J. 2005, 11, 4257-4262
29. Gáti, T.; Tóth, G.; Drabowicz, J.; Moeller, S.; Hofer, E.; Polavarapu, P.; Duddeck, H. Chirality 2005, 17, S40-S47
30. Lindgren, B. Acta Chem. Scand. 1972, 26, 2560-2561
31. Zhang, J.; Koizumi, T. Phosphorus, Sulfur Silicon Relat. Elem. 2000, 157, 225-252
32. Zhang, J.; Takahashi, S.; Saito, S.; Koizumi, T. Tetrahedron: Asymmetry 1998, 9, 3303-3317
33. For NMR and computational studies of aza- and oxyselenuranes produced by oxidation of selenomethionine, see: Ritchey, J. A.; Davis, B. M.; Pleban, P. A.; Bayse, C. A. Org. Biomol. Chem. 2005, 3, 4337-4342
34. For a recent report on the use of related cyclic seleninate esters as catalysts for the racemic oxidations of sulfides to sulfoxides, alkenes to epoxides, and enamines to α-hydroxyketones, see: Mercier, E. A.; Smith, C. D.; Parvez, M.; Back, T. G. J. Org. Chem. 2012, 77, 3508-3517
35. Oki, M. Applications of Dynamic NMR Spectroscopy to Organic Chemistry; VCH: Weinheim, Germany, 1985.
36. Sandström, J. Dynamic NMR Spectroscopy; Academic Press: London, 1982.
37. Lambert, J. B.; Mazzola, E. P. Nuclear Magnetic Resonance Spectroscopy; Pearson-Prentice Hall: Upper Saddle River, NJ, 2004; Chapter 5.2.
38. Bergman, J.; Engman, L.; Sidén, J. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1986; Vol. 1, Chapter 14.
39. Drabowicz, J.; Kielbasinski, P.; Zajac, A. In The Chemistry of Organic Selenium and Tellurium Compounds; Rappoport, Z., Ed.; Wiley: Chichester, U.K., 2012; Vol. 3, Part 2, Chapter 15.
40. Drabowicz, J.; Mikolajczyk, M. In Organoselenium Chemistry; Wirth, T., Ed.; Springer-Verlag: Berlin, 2000; pp 143-176.
41. Sato, S.; Takahashi, O.; Furukawa, N. Coord. Chem. Rev. 1998, 176, 483-514
42. Adzima, L. J.; Martin, J. C. J. Org. Chem. 1977, 42, 4006-4016
43. Astrologes, G. W.; Martin, J. C. J. Am. Chem. Soc. 1976, 98, 2895-2900
44. Reich, H. J. J. Am. Chem. Soc. 1973, 95, 964-966
45. Denney, D. B.; Denney, D. Z.; Hsu, Y. F. J. Am. Chem. Soc. 1978, 100, 5982-5983
46. Denney, D. B.; Denney, D. Z.; Hammond, P. J.; Hsu, Y. F. J. Am. Chem. Soc. 1981, 103, 2340-2347
47. 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 09, revision A.01; Gaussian, Inc.: Wallingford, CT, 2009.
48. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
49. Perdew, J. P.; Wang, Y. Phys. Rev. B 1992, 45, 13244-13249
50. Ab Initio Molecular Orbital Theory; Hehre, W. J.; Radom, L.; von R. Schleyer, P.; Pople, J. A., Eds.; John Wiley & Sons: New York, 1986.
51. Pearson, J. K.; Ban, F.; Boyd, R. J. J. Phys. Chem. A 2005, 109, 10373-10379
52. Heverly-Coulson, G. S.; Boyd, R. J. J. Phys. Chem. A 2011, 115, 4827-4831
53. Berry, R. S. J. Chem. Phys. 1960, 32, 933-938
54. Whitesides, G. M.; Mitchell, H. L. J. Am. Chem. Soc. 1969, 91, 5384-5386
55. Ugi, I.; Marquarding, D.; Klusacek, H.; Gillespie, P.; Ramirez, F. Acc. Chem. Res. 1971, 4, 288-296
56. Muetterties, E. L. J. Am. Chem. Soc. 1969, 91, 1636-1643
57. Muetterties, E. L. J. Am. Chem. Soc. 1969, 91, 4115-4122
58. Moberg, C. Angew. Chem., Int. Ed. 2011, 50, 10290-10292
59. Cass, M. E.; Hii, K. K.; Rzepa, H. S. J. Chem. Educ. 2006, 83, 336
60. Bürgi, H. B.; Dunitz, J. D. Acc. Chem. Res. 1983, 16, 153-161
61. Mislow, K. Acc. Chem. Res. 1970, 3, 321-331
62. For pseudorotations in sulfur compounds, see: Oae, S. Organic Sulfur Chemistry: Structure and Mechanism; CRC Press: Boca Raton, FL, 1991; pp 18-21.
63. Muetterties, E. L.; Mahler, W.; Schmutzler, R. Inorg. Chem. 1963, 2, 613-618
64. Muetterties, E. L.; Mahler, W.; Packer, K. J.; Schmutzler, R. Inorg. Chem. 1964, 3, 1298-1303
65. Gorenstein, D.; Westheimer, F. H. J. Am. Chem. Soc. 1970, 92, 634-644
66. Ogawa, S.; Sato, S.; Erata, T.; Furukawa, N. Tetrahedron Lett. 1992, 33, 1915-1918
67. Couzijn, E. P. A.; Slootweg, J. C.; Ehlers, A. W.; Lammertsma, K. J. Am. Chem. Soc. 2010, 132, 18127-18140
68. Mauksch, M.; von R. Schleyer, P. Inorg. Chem. 2001, 40, 1756-1769
69. Mislow, K. Science 1954, 120, 232-233
70. Mislow, K.; Bolstad, R. J. Am. Chem. Soc. 1955, 77, 6712-6713
71. Brinkmann, T.; Uzar, H. C. J. Chem. Soc., Perkin Trans. 2 2000, 527-530
72. Wiegrefe, A.; Brinkmann, T.; Uzar, H. C. J. Phys. Org. Chem. 2001, 14, 205-209
73. Jameson, C. J. Annu. Rev. Phys. Chem. 1996, 47, 135-169
74. Jameson, A. K.; Jameson, C. J. J. Am. Chem. Soc. 1973, 95, 8559-8561
75. Cross, B. P.; Schleich, T. Org. Magn. Reson. 1977, 10, 82-85
76. Hoffman, R. E.; Becker, E. D. J. Magn. Reson. 2005, 176, 87-98
77. Ammann, C.; Meier, P.; Merbach, A. E. J. Magn. Reson. 1982, 46, 319-321
78. Van Geet, A. L. Anal. Chem. 1968, 40, 2227-2229
79. Van Geet, A. L. Anal. Chem. 1970, 42, 679-680
80. Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49-56
81. Peng, C.; Schlegel, H. B. Isr. J. Chem. 1993, 33, 449-454
82. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161
83. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527
84. Ditchfield, R. Mol. Phys. 1974, 27, 789-807
85. Gee, C. H.; Raynes, W. T. Chem. Phys. Lett. 2000, 330, 595-602
86. Ruud, K.; Astrand, P.-O.; Taylor, P. R. J. Am. Chem. Soc. 2001, 123, 4826-4833
87. Sabzyan, H.; Buzari, B. Chem. Phys. 2008, 352, 297-305