1hJFH coupling in 2-fluorophenol revisited: Is intramolecular hydrogen bond responsible for this long-range coupling?

Magnetic Resonance in Chemistry

Volumn 49, Issue 12, 2011, Pages 763-767

  Cormanich, Rodrigo A ^a   Moreira, Marilua A ^b   Freitas, Matheus P ^b   Ramalho, Teodorico C ^b   Anconi, Cléber P A ^b   Rittner, Roberto ^a   Contreras, Rubén H ^c   Tormena, Cláudio F ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b FEDERAL UNIVERSITY OF LAVRAS   (Brazil)

^c Ciudad Universitaria   (Argentina)

Author keywords

2 fluorophenol; coupling constant; FCCP CMO; intramolecular H bonding; QTAIM

Indexed keywords

HYDROGEN BONDS; QUANTUM THEORY;

2-FLUOROPHENOL; COUPLING CONSTANTS; FCCP-CMO; FERMI CONTACT TERM; FLUORINE ATOMS; INTRAMOLECULAR H-BONDING; INTRAMOLECULAR HYDROGEN BOND; OH-GROUPS; QTAIM; SPIN-SPIN COUPLINGS;

MOLECULAR ORBITALS;

2 FLUOROPHENOL; 2-FLUOROPHENOL; ACETONITRILE; ACETONITRILE DERIVATIVE; CYCLOHEXANE; CYCLOHEXANE DERIVATIVE; PHENOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON; HYDROGEN BOND; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYSICAL CHEMISTRY; QUANTUM THEORY; THERMODYNAMICS;

ACETONITRILES; CHEMISTRY, PHYSICAL; CYCLOHEXANES; ELECTRONS; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PHENOLS; QUANTUM THEORY; THERMODYNAMICS;

EID: 83855163977     PISSN: 07491581     EISSN: 1097458X     Source Type: Journal    
DOI: 10.1002/mrc.2838     Document Type: Article

References (40)

1. J. Dingley, S. Grzesiek, J. Am. Chem. Soc. 1998, 120, 8293.
2. K. Pervushin, A. Ono, C. Fernandez, T. Szyperski, M. Kainosho, K. Wüthrich, Proc. Natl. Acad. Sci. USA 1998, 95, 14147.
3. I. Alkorta, J. Elguero, G. S. Denisov, Magn. Reson. Chem. 2008, 46, 599.
4. J. B. Rowbotham, M. Smith, T. Schaefer, Can. J. Chem. 1975, 53, 986.
5. M. L. Senent, A. Niño, C. Muñoz-Caro, Y. G. Smeyers, R. Domínguez-Gomez, J. M. Orza, J. Phys. Chem. A 2002, 106, 10673.
6. S. J. Grabowski, Chem. Rev. 2011, 111, 2597.
7. J. D. Dunitz, R. Taylor, Chem. Eur. J. 1997, 3, 89.
8. A. C. Legon, Angew. Chem. Int. Ed. 1999, 38, 2686.
9. P. Metrangolo, G. Resnati, Chem. Eur. J. 2001, 7, 2511.
10. F. Zordan, L. Brammer, P. Sherwood, J. Am. Chem. Soc. 2005, 127, 5979.
11. S. J. Grabowski, E. Bilewicz, Chem. Phys. Lett. 2006, 427, 51.
12. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Revision E.01, Gaussian: Wallingford CT, 2004.
13. J. Geertsen, J. Oddershede, J. Chem. Phys. 1984, 90, 301.
14. T. Enevoldsen, J. Oddershede, S. P. A. Sauer, Theor. Chem. Acc. 1998, 100, 275.
15. E. S. Nielsen, P. Jørgensen, J. Oddershede, J. Chem. Phys. 1980, 73, 6238.
16. J. Dalton, A Molecular Electronic Structure Program, Release 2.0 2005, see.
17. E. D. Glendening, J. K. Badenhoop, A. E. Reed, J. E. Carpenter, J. A. Bohmann, C. M. Morales, F. Weinhold,. NBO 5.0. Theoretical Chemistry Institute, University of Wisconsin: Madison, 2001.
18. T. A. Keith, AIMAll (Version 11.06.19). T.K Gristmill Software, Overland Park KS, USA, 2011 ()
19. R. F. W. Bader, Atoms in Molecules: A Quantum Theory, Clarendon, Oxford, 1990.
20. R. F. W. Bader, Chem. Eur. J. 2006, 12, 2896.
21. I. Mata, I. Alkorta, E. Espinosa, E. Molins, J. Elguero, in The Quantum Theory of Atoms in Molecules, from Solid State to DNA and Drug Design (Eds:, C. F. Matta, R. J. Boyd,), WILEY-VHC, Weinheim, 2007.
22. S. J. Grabowski, in The Quantum Theory of Atoms in Molecules, from Solid State to DNA and Drug Design (Eds:, C. F. Matta, R. J. Boyd,), WILEY-VHC, Weinheim, 2007.
23. a) J. E. Perez, F. S. Ortiz, R. H. Contreras, C. G. Giribet, M. C. Ruiz de Azúa, J. Mol. Struct. (THEOCHEM) 1990, 210, 193
24. b) A. V. Afonin, J. E. Pérez, M. C. Ruiz de Azúa, R. H. Contreras, P. Lazzeretti, Russ. Chem. Bull., 46, 306-309, 1997.
25. R. H. Contreras, G. Gotelli, L. C. Ducati, T. M. Barbosa, C. F. Tormena, J. Phys. Chem. A 2010, 114, 1044.
26. P. R. Anizelli, D. C. Favaro, R. H. Contreras, C. F. Tormena, J. Phys. Chem. A, 2011, 115, 5684.
27. J. Oddershede, in Advances in Quantum Chemistry, Vol. 11 (Ed:, P.-O. Löwdin,) Academic Press, New Your, 1978, p. 275.
28. A. C. Diz, C. G. Giribet, M. C. Ruiz de Azúa, R. H. Contreras, Int. J. Quantum Chem. 1990, 37, 663.
29. G. A. Aucar, R. H. Romero, A. F. Maldonado, Int. Rev. Phys. Chem. 2010, 29, 1.
30. R. H. Contreras, M. C. Ruiz de Azúa, C. G. Giribet, G. A. Aucar, R. Lobayan de Bonczok, J. Mol. Struct. (THEOCHEM) 1993, 284, 249.
31. A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899.
32. F. Weinhold In, Encyclopedia of Computational Chemistry, (Ed., Schleyer, P. v. R.,), Wiley, New York, 1998, Vol. 3, p. 1792.
33. A. Soncini, P. Lazzeretti, J. Chem. Phys. 2003, 119, 1343.
34. J. D. Vilcachagua, L. C. Ducati, R. Rittner, R. H. Contreras, C. F. Tormena, J. Phys. Chem. A 2011, 115, 7762 and references cited therein.
35. D. Rae, J. A. Weigold, R. H. Contreras, G. Yamamoto, Magn. Reson. Chem. 1992, 30, 1047. and references cited therein.
36. I. G. Shenderovich, S. N. Smirnov, G. S. Denisov, V. A. Gindin, N. S. Golubev, A. Dunger, R. Reibke, S. Kirpekar, O. L. Malkina, H. H. Limbach, Ber Bunsenges. Phys. Chem. 1998, 102, 422.
37. I. G. Shenderovich, H. H. Limbach, S. N. Smirnov, P. M. Tolstoy, G. S. Denisov, N. S. Golubev, Phys. Chem. Chem. Phys. 2002, 4, 5488.
38. N. S. Golubev, I. G. Shenderovich, S. N. Smirnov, G. S. Denisov, H.-H. Limbach, Chem. Eur. J. 1999, 5, 492.
39. P. Schah-Mohammedi, I. G. Shenderovich, C. Detering, H.-H. Limbach, P. M. Tolstoy, S. N. Smirnov, G. S. Denisov, N. S. Golubev, J. Am. Chem. Soc. 2000, 122, 12878.
40. J. E. Del Bene, S. A. Perera, R. J. Bartlett, J. Am. Chem. Soc. 2000, 122, 3560.