The low-barrier hydrogen bond of deuterated benzoylacetone probed by very low temperature neutron and X-ray diffraction studies and theoretical calculations

Chemistry - A European Journal

Volumn 13, Issue 19, 2007, Pages 5539-5547

  Madsen, Georg K H ^a   McIntyre, Garry J ^b   Schiøtt, Birgit ^a   Larsen, Finn K ^a  

^a AARHUS UNIVERSITY   (Denmark)

^b Lnstitue Laue Langevin   (France)

Author keywords

Deuterium; Enzyme catalysis; Hydrogen bonds; Low barrier tunneling; Neutron diffraction

Indexed keywords

AROMATIC COMPOUNDS; DEUTERIUM; ENZYME ACTIVITY; HYDROGEN BONDS; NEUTRON DIFFRACTION; PROBABILITY DENSITY FUNCTION;

BENZOYLACETONE; HYDROGEN POTENTIALS; LOW BARRIER TUNNELING;

ACETONE;

EID: 34547307213     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601490     Document Type: Article

References (50)

1. F. Hibbert, J. Emsley, Adv. Phys. Org. Chem. 1990, 26, 255-379.
2. G. A. Jeffrey, An introduction to Hydrogen Bonding, Oxford University Press, 1997.
3. T. Steiner, Angew. Chem. 2002,114, 50-80;
4. Angew. Chem. Int. Ed. 2002, 41, 48-76.
5. W. W. Cleland, Biochemistry 1992, 31, 317-319.
6. P. Gilli, V. Bertolasi, V. Ferretti, G. Gilli, J. Am. Chem. Soc. 1994, 116, 909-915.
7. G. K. H. Madsen, B. B. Iversen, F. K. Larsen, M. Kapon, G. M. Reisner, F. H. Herbstein, J. Am. Chem. Soc. 1998, 120, 10040-10045.
8. C. Flensburg. S. Larsen, R. F. Stewart, J. Phys. Chem. 1995, 99, 10130-10141.
9. a)W. W. Cleland, M. M. Krevoy. Science 1994, 264, 1887-1890;
10. b) P. A. Frey, S. A. Whitt, J. B. Tobin, Science 1994, 264, 1927-1930;
11. c) A. Warshel, A. Papazyan, P. A. Kollman, W. W. Cleland, M. M. Kreevoy, P. A. Frey, Science 1995, 269, 102-106.
12. P. A. Frey, J. Phys. Org. Chem. 2004, 17, 511-520.
13. C. N. Schutz, A. Warshel, Proteins: Struct., Fund, Bioinf. 2004, 55, 711-723.
14. C. N. Fuhrmann, M. D. Daugherty, D. A. Agard, J. Am. Chem. Soc. 2006, 128, 9086-9102.
15. a) M. Benoit, D. Marx, M. Parrinello, Nature 1998, 392, 258-261;
16. b) M. Benoit, D. Marx, ChemPhysChem 2005, 6, 1738-1741.
17. C. C. Wilson, Acta Crystallogr. Sect. B 2001, 57, 435-439.
18. C. A. Morrison, M. M. Siddick, P. J. Camp, C. C. Wilson, J. Am. Chem. Soc. 2005, 127, 4042-4048.
19. F. Fontaine-Vive, M. R. Johnson, G. J. Kearley, J. A. K. Howard, S. F. Parker, J. Am. Chem. Soc. 2006, 128, 2963-2969.
20. T. Steiner, I. Marjerz, C. C. Wilson, Angew. Chem. 2001, 113, 2728-2731;
21. Angew. Chem. Int. Ed. 2001, 40, 2651-2654.
22. J. A. Cowan, J. A. K. Howard, G. J. Mclntyre, S. M.-F. Lo, I. D. Williams, Acta Crystallogr. Sect. B 2003, 59, 794 - 801.
23. J. A. Cowan, J. A. K. Howard, G. J. Mclntyre, S. M.-F. Lo, I. D. Williams, Acta Crystallogr. Sect. B 2005, 61 ,'724-730.
24. E. O. Schlemper, W. C. Hamilton, S. T. La Placa, J. Chem. Phys. 1971, 54, 3990-4000.
25. B. Hsu, E. O. Schlemper, C. K. Fair, Acta Crystallogr. Sect. B 1980, 36, 1387-1391.
26. a) J. D. Dunitz, V. Schomaker, K. N. Trueblood, J. Phys. Chem. 1988, 92, 856-867;
27. b)J.D. Dunitz, E. F. Maverick, K. N. Trueblood, Angew. Chem. 1988, 100, 910-926;
28. Angew. Chem. Int. Ed. Engl. 1988, 27, 880-895.
29. F. L. Hirshfeld, Acta Crystallogr. Sect. A 1976, 32, 239-244.
30. K. Wolf, W. Mikenda, E. Nusterer, K. Schwarz, C. Ulbricht, Chem. Eur.J. 1998, 4, 1418-1427.
31. M. Ichikawa, Acta Crystallogr. Sect. B 1978, 34, 2074-2080.
32. F. Takusagawa, T. F. Koetzle, Acta Crystallogr. Sect. B 1979, 35, 2126-2135.
33. F. H. Herbstein, B.B. Iversen, M. Kapon, F. K. Larsen, G. K. H. Madsen, G. M. Reisner, Acta Crystallogr. Sect. B 1999, 55, 767-787.
34. V. Barone, C. Adamo, J. Chem. Phys. 1996, 105, 11007-11019.
35. K. Hinsen, B. Roux, J. Chem. Phys. 1997, 106, 3567-3577.
36. M. E. Tuckerman, D. Marx, Phys. Rev. Lett. 2001, 86, 4946-4949.
37. R. Iftime, J. Schofield, J. Chem. Phys. 2001, 114, 6763-6773.
38. J. A. Belot, J. Clark, J. A. Cowan, G. S. Harbison, A. I. Kolesnikov, Y.-S. Kye, A. J. Schultz, C. Silvernail, X. Zhao, J. Phys. Chem. B 2004, 108, 6922-6926.
39. G. K. H. Madsen, C. Wilson, T. M. Nymand, G. J. Mclntyre, F. K. Larsen, J. Phys. Chem. A 1999, 103, 8684-8690.
40. T. Steiner, W. Saenger, Acta Crystallogr. Sect. B 1994, 50, 348-357.
41. B. T. M. Willis, A. W. Pryor, Thermal Vibrations in Crystallography, Cambridge University Press, 1975.
42. This is seen from the plot of the thermal ellipsoids in CTMH. Unfortunately the MSD of the hydrogen are not included in the attached structure in reference [31] Therefore we can not study it quantitatively.
43. It should also be pointed out that the RMSD is actually a small number compared to the distances covered by the enol hydrogen. To just cover 50% of the probability density distribution a distance of 1.54 times the RMSD is needed.
44. P. Gilli, V. Bertolasi, L. Pretto, V. Feretti, G. Gilli, J. Am. Chem. Soc. 2004, 126, 3845-3855.
45. T. Koritsanszky, S. Howard, P. R. Mallinson, Z. Su. T. Richter, N. K. Hansen, XD, a computer program package for multipole refinement and analysis of charge densities from diffraction data, Institute of Crystallography, Freie Universität, Berlin, 1995.
46. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
47. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
48. T. H. Dunning, Jr., J. Chem. Phys. 1989, 90,1007-1023.
49. Gaussian 03, Revision B.05, 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. akrzewski, 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, Gaussian, Inc., Wallingford CT, 2004.
50. G. K. H. Madsen, G. Santi, Phys. Rev. B 2005 72, 220301 (R.