Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives

Journal of Physical Chemistry A

Volumn 115, Issue 50, 2011, Pages 14539-14545

  Favaro, Denize C ^a   Ducati, Lucas C ^a   Dos Santos, Francisco P ^a   Contreras, Ruben H ^b   Tormena, Claudio F ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVES; COUPLING CONSTANTS; EXPERIMENTAL STUDIES; FERMI CONTACT; HALOGEN ATOMS; LONE PAIR; SPIN COUPLING CONSTANTS; STRONG INTERACTION;

BROMINE; CHLORINE;

COUPLINGS;

EID: 84055187650     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp2083456     Document Type: Article

References (43)

1. Karplus, M. J. Chem. Phys. 1959, 30, 11.
2. Karplus, M. J. Phys. Chem. 1960, 64, 1793.
3. Karplus, M. J. Am. Chem. Soc. 1963, 85, 2870.
4. Thomas, W. A. Prog. Nucl. Magn. Reson. Spectrosc. 1997, 30, 183.
5. Parella, T.; Sanchez-Ferrando, F.; Virgili, A. Magn. Reson. Chem. 1992, 14, 657.
6. Liu, M.; Farran, R D.; Gillam, J. M.; Nicholson., J. K; Lindon, J. C. J. Magn. Reson. 1995, 109, 275.
7. Kover, K. E. J. Magn. Reson. 2006, 181, 89.
8. dos Santos, F. P.; Tormena, C. F.; Contreras, R. H.; Rittner, R.; Magalhaes, A. Magn. Reson. Chem. 2008, 46, 107.
9. San-Fabián, J.; Guilleme, J.; Díez, E.; Lazzeretti, P.; Malagoli, M.; Zanasi, R.; Mora, A L. Mol. Phys. 1994, 82, 913.
10. Guilleme, J.; San-Fabian, J.; Díez, E. Mol. Phys. 1997, 91, 243.
11. San-Fabián, J.; Guilleme, J.; Díez, E. Av. Quím. 1995, 91, 200.
12. Barfield, M.; Smith, W. B. J. Am. Chem. Soc. 1992, 114, 1574.
13. Smith, W. B.; Barfield, M. Magn. Reson. Chem. 1993, 31, 696.
14. VanWijk, J.; Huckriede, B. D.; Ippel, J. H.; Altona, C. Methods Enzymol. 1992, 211, 286.
15. Lohr, F.; Schmidt, J. M.; Ruterjans, H. J. Biomol. NMR 1999, 14, 1.
16. Barone, V.; Peralta, J. E.; Contreras, R H. J. Comput. Chem. 2001, 22, 1615.
17. Contreras, R. H.; Suardíaz, R; Pérez, C.; Crespo-Otero, R.; San Fabián, J.; García de la Vega, J. M. J. Chem. Theory Comput. 2008, 4, 1494.
18. Contreras, R. H.; Suardíaz, R; Pérez, C.; Crespo-Otero, R.; San Fabián, J.; García de la Vega, J. M. Int. J. Quantum Chem. 2010, 110, 532.
19. Perez, C.; Suardíaz, R; Ortiz, P. J.; Crespo-Otero, R.; Bonetto, G. M.; Gavín, J. A; García de la Vega, J. M.; San Fabián, J.; Contreras, R H. Magn. Reson. Chem. 2008, 46, 846.
20. Contreras, R. H.; Peralta, J. E. Prog. Nucl. Magn. Reson. Spectrosc. 2000, 37, 321.
21. (a) Vitorge, M. C.; Chenon, M. T.; Coupry, C.; Lumbroso-Bader, N. Org Magn. Reson. 1983, 21, 20.
22. (b) Contreras, R H.; Natiello, M. A.; Tufró, M. F.; De Kowalewski, D. G; Scuseria, G. E. Z. Phys. Chem. 1986, 267, 289.
23. Nolis, P.; Espinosa, J. F.; Parella, T. J. Magn. Reson. 2006, 180, 39.
24. Sychrovshý, V; Gräfenstein, J.; Cremer, D. J. Chem. Phys. 2000, 113, 3530.
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A; Cheeseman, J. R; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V; Mennucci, B.; Cossi, M.; Scalmani, G; Rega, N.; Petersson, G. A; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; 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.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J.J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A G; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G; Liashenko, A; Piskorz, P.; Komaromi, I.; Martin, R L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
26. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F. NBO 5.0G; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 2001; http://www.chem.wisc.edu/ ~nbo5/, program as implemented in the Gaussian03 package.
27. (a) Becke, A D. Phys. Rev. A 1988, 38, 3098.
28. (b) Becke, A D. J. Chem. Phys. 1993, 98, 5648.
29. (c) Lee, C. T.; Yang, W. T.; Parr, R. G Phys. Rev. B 1988, 37, 785.
30. Woon, D. E.; Dunning, T. H. J. Chem. Phys. 1993, 98, 1358.
31. Barone, V. J. Chem. Phys. 1994, 10, 6834.
32. Marshall, J. L.; Walter, S. R; Barfield, M.; Marchand, A. P.; Segré, A. L. Tetrahedron 1976, 32, 537.
33. Cheng, M.; Pu, X.; Wang, N.-B.; Li, M.; Tian, A. New J. Chem. 2008, 32, 1060.
34. Anizelli, P. R.; Favaro, D. C.; Contreras, R. H.; Tormena, C. F. J. Phys. Chem. A 2011, 115, 5684.
35. Vilcachagua, J. D.; Ducati, L. C.; Rittner, R.; Contreras, R H.; Tormena, C. F. J. Phys. Chem. A 2011, 115, 7762 and references cited therein.
36. (a) Oddershede, J. Polarization Propagator Calculations. In Advances in Quantum Chemistry; P.-O. Lowdin, Ed.; Elsevier: New York, 1978; Vol. 11, p 272.
37. (b) Diz, A. C.; Giribet, C. G; Ruiz de Azúa, M. C.; Contreras, R H. Int. J. Quantum Chem. 1990, 37, 663.
38. (c) Electronic origin of high resolution NMR parameters. Contreras, R. H.; Giribet, C. G; Ruiz de Azúa, M. C.; Ferraro, M. B. Studies in Physical and Theoretical Chemistry. In Structure, Interactions and Reactivity; Fraga, S., Ed.; Elsevier: New York, 1992; Vol. 77B, Chapter 7, p 212.
39. (d) Contreras, R H.; Ruiz de Azúa, M. C.; Giribet, C. G; Aucar, G. A; Lobayan de Bonczok, R J. Mol. Struct. (Theochem) 1993, 284, 249.
40. (e) Giribet, C. G; Ruiz de Azúa, M. C.; Contreras, R H.; Lobayan de Bonczok, R.; Aucar, G. A; Gomez, S. J. Mol. Struct. (Theochem) 1993, 300, 467.
41. Contreras, R H.; Esteban, A L.; Diez, E.; Head, N. J.; Della, E. W. Mol. Phys. 2006, 104, 485.
42. Contreras, R H.; dos Santos, F. P.; Ducati, L. C.; Tormena, C. F. Magn. Reson. Chem. 2010, 48, S151.
43. Barfield, M.; Chakrabarty, B. Chem. Rev. 1969, 69, 757.