Probing hyperconjugation experimentally with the conformational deuterium isotope effect

Journal of Organic Chemistry

Volumn 77, Issue 20, 2012, Pages 9221-9226

  Greenway, Kyle T ^a   Bischoff, Anthony G ^a   Pinto, B Mario ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANOMERIC EFFECT; CHALCOGENS; CHEMICAL PHENOMENAS; CONFORMATIONAL EQUILIBRIUM; DEUTERIUM ISOTOPE EFFECT; DFT CALCULATION; HYPERCONJUGATION; NATURAL BOND ORDERS; PERTURBATION METHOD; PRACTICAL IMPORTANCE; VARIABLE TEMPERATURE;

CARRIER MOBILITY; DENSITY FUNCTIONAL THEORY; DEUTERIUM; ETHERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXYGEN; SELENIUM; SULFUR;

CONFORMATIONS;

1,3 DITHIANE DERIVATIVE; CHALCOGEN; DEUTERIUM; DIOXANE; OXYGEN; SELENIUM DERIVATIVE; SULFUR;

ARTICLE; CHEMICAL INTERACTION; CONFORMATION; CONJUGATION; DENSITY FUNCTIONAL THEORY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TEMPERATURE DEPENDENCE;

DEUTERIUM; DIOXANES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; ORGANOSELENIUM COMPOUNDS; OXYGEN; QUANTUM THEORY; QUINOLIZINES; SELENIUM; SULFUR; SULFUR COMPOUNDS; TEMPERATURE;

EID: 84867731140     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3017988     Document Type: Article

References (40)

1. Edward, J. T. Chem. Ind. 1955, 36, 1102-1104
2. Lemieux, R. U.; Chu, N. J. In Abstracts of Papers; 133rd National Meeting of the American Chemical Society; San Francisco, CA, 1958; Vol. 33, p 31N.
3. Albright, T. A.; Burdett, J. K.; Whangbo, M. Orbital Interactions in Chemistry; 1 st ed.; Wiley: Chichester, UK, 1985.
4. Mulliken, R. S. J. Chem. Phys. 1939, 7, 339-352
5. Mulliken, R. S.; Rieke, C. A.; Brown, W. G. J. Am. Chem. Soc. 1941, 63, 41-56
6. Alabugin, I. V.; Gilmore, K. M.; Peterson, P. W. WIREs Comput. Mol. Sci. 2011, 1, 109-141
7. Whangbo, M.-H.; Wolfe, S. Isr. J. Chem. 1980, 20, 36-42
8. Goodman, L.; Gu, H.; Pophristic, V. J. Phys. Chem. A 2005, 109, 1223-1229
9. Braida, B.; Prana, V.; Hiberty, P. C. Angew. Chem., Int. Ed. 2009, 48, 5724-5728
10. Alabugin, I. V.; Zeidan, T. A. J. Am. Chem. Soc. 2002, 124, 3175-3185
11. Alabugin, I. V. J. Org. Chem. 2000, 65, 3910-3919
12. Pinto, B. M.; Schlegel, H. B.; Wolfe, S. Can. J. Chem. 1987, 65, 1658-1662
13. Cocinero, E. J.; Carcabal, P.; Vaden, T. D.; Simons, J. P.; Davis, B. G. Nature 2011, 469, 76-79
14. Wang, C.; Ying, F.; Wu, W.; Mo, Y. J. Am. Chem. Soc. 2011, 133, 13731-13736
15. Saunders, M.; Jaffe, M. H.; Vogel, P. J. Am. Chem. Soc. 1971, 93, 2558-2559
16. Mo, Y. Nat. Chem. 2010, 2, 666-671
17. Romers, C.; Altona, C.; Buys, H. R.; Havinga, E. In Topics in Stereochemistry; Eliel, E. L.; Allinger, N. L., Eds.; John Wiley & Sons, Inc.: Hoboken, NJ; Vol. 4, pp 39-97.
18. Wolfe, S.; Pinto, B. M.; Varma, V.; Leung, R. Y. N. Can. J. Chem. 1990, 68, 1051-1062
19. Juaristi, E.; Cuevas, G. Acc. Chem. Res. 2007, 40, 961-970
20. Bohlmann, F. Angew. Chem. 1957, 69, 641-642
21. Wolfe, S.; Kim, C.-K. Can. J. Chem. 1991, 69, 1408-1412
22. Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019-5087
23. Bailey, W. F.; Rivera, A. D.; Rossi, K. Tetrahedron Lett. 1988, 29, 5621-5624
24. Anet, F. A. L.; Kopelevich, M. J. Chem. Soc., Chem. Commun. 1987, 595-598
25. Juaristi, E.; Cuevas, G.; Vela, A. J. Am. Chem. Soc. 1994, 116, 5796-5804
26. Anet, F. A. L.; Kopelevich, M. J. Am. Chem. Soc. 1986, 108, 2109-2110
27. Batchelor, R. J.; Einstein, F. W. B.; Gay, I. D.; Gu, J. H.; Johnston, B. D.; Pinto, B. M. J. Am. Chem. Soc. 1989, 111, 6582-6591
28. Pinto, B. M.; Johnston, B. D.; Nagelkerke, N. Heterocycles 1989, 28, 389-403
29. Mikoajczyk, M.; Mikina, M.; Graczyk, P.; Wieczorek, M. W.; Bujacz, G. Tetrahedron Lett. 1991, 32, 4189-4192
30. Pinto, B. M.; Sandoval-Ramirez, J.; Dev Sharma, R. Tetrahedron Lett. 1985, 26, 5235-5238
31. Pinto, B. M.; Johnston, B. D.; Sandoval-Ramirez, J.; Sharma, R. D. J. Org. Chem. 1988, 53, 3766-3771
32. Cheeseman, J. R.; Trucks, G. W.; Keith, T. A.; Frisch, M. J. J. Chem. Phys. 1996, 104, 5497-5509
33. Merrick, J. P.; Moran, D.; Radom, L. J. Phys. Chem. A 2007, 111, 11683-11700
34. Reed, A. E.; Weinhold, F. J. Chem. Phys. 1985, 83, 1736-1740
35. Bickelhaupt, F. M.; Baerends, E. J. Angew. Chem., Int. Ed. 2003, 42, 4183-4188
36. Ouzounian, J. G.; Anet, F. A. L. J. Labelled Compd. Radiopharm. 1986, 23, 401-404
37. Hanley, J. A.; Forsyth, D. A. J. Labelled Compd. Radiopharm. 1990, 28, 307-310
38. Eliel, E. L.; Smith, V. S.; Hutchins, R. O. J. Org. Chem. 1975, 40, 524-526
39. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100
40. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789