Theoretical and X-ray crystallographic evidence of a fluorine-imine gauche effect: An addendum to dunathan's stereoelectronic hypothesis

Chemistry - A European Journal

Volumn 17, Issue 32, 2011, Pages 8850-8857

  Sparr, Christof ^a   Salamanova, Evdokiya ^b   Schweizer, W Bernd ^a   Senn, Hans Martin ^b   Gilmour, Ryan ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

aldimines; conformation analysis; density functional theory; fluorine; gauche effect

Indexed keywords

ALDIMINES; ANTIPERIPLANAR; C-F BONDS; CONFORMATION ANALYSIS; CONJUGATED IMINE; DFT METHOD; EXTERNAL SYSTEMS; GAUCHE CONFORMATION; GAUCHE EFFECTS; PYRIDOXAL PHOSPHATES; SINGLE CRYSTAL X-RAY DIFFRACTION ANALYSIS; TORSION ANGLE;

ENZYME INHIBITION; FLUORINE; NITROGEN COMPOUNDS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

DENSITY FUNCTIONAL THEORY;

FLUORINATED HYDROCARBON; FLUORINE; IMINE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; CONFORMATION; METHODOLOGY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; FLUORINE; HYDROCARBONS, FLUORINATED; IMINES; MODELS, CHEMICAL; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 79960618458     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100644     Document Type: Article

References (49)

1. H. C. Dunathan, Proc. Natl. Acad. Sci. USA 1966, 55, 712-716.
2. C. T. Walsh, Enzymatic Reaction Mechanisms, 2 nd ed., W. H. Freeman, San Fransisco, 1979
3. J. C. Vederas, H. G. Floss, Acc. Chem. Res. 1980, 13, 455-463
4. H. Hayashi, H. Wada, T. Yoshimura, N. Esaki, K. Soda, Annu. Rev. Biochem. 1990, 59, 87-110
5. H. Hayashi, J. Biochem. 1995, 118, 463-473
6. A. C. Eliot, J. F. Kirsch, Annu. Rev. Biochem. 2004, 73, 383-415
7. T. D. H. Bugg, in Introduction to Enzyme and Coenzyme Chemistry, 2 nd ed., Wiley-Blackwell, New York, 2004, pp. 211-226.
8. C. T. Walsh, Annu. Rev. Biochem. 1984, 53, 493-535.
9. B. Lippert, B. W. Metcalf, R. J. Resvick, Biochem. Biophys. Res. Commun. 1982, 108, 146-152
10. W. S. Faraci, C. T. Walsh, Biochemistry 1989, 28, 431-437
11. D. B. Berkowitz, K. R. Karukurichi, R. De La Salud-Bea, D. L. Nelson, C. D. McCune, J. Fluorine Chem. 2008, 129, 731-742
12. D. B. Berkowitz, K. R. Karukurichi, R. De La Salud-Bea, G. Maiti, J. M. McFadden, M. L. Morris, ACS Symp. Ser. 2009, 1009, 288-303
13. D. B. Berkowitz, R. de La Salud-Bea, W.-J. Jahng, Org. Lett. 2004, 6, 1821-1824.
14. D. Murali, L. G. Flores, A. D. Roberts, R. J. Nickles, O. T. DeJesus, Appl. Radiat. Isot. 2003, 59, 237-243.
15. M. G. Palfreyman, C. Danzin, P. Bey, M. J. Jung, G. Ribereau-Gayon, M. Aubry, J. P. Vevert, A. Sjoerdsma, J. Neurochem. 1978, 31, 927-932.
16. M.-D. Tsai, H. J. R. Weintraub, S. R. Byrn, C. Chang, H. G. Floss, Biochemistry 1978, 17, 3183-3188
17. L. Casella, M. Gullotti, J. Am. Chem. Soc. 1983, 105, 803-809
18. M. Nagata, M. Doi, M. Inoue, T. Ishida, M. Kamigauchi, M. Sugiura, A. Wakahara, J. Chem. Soc. Perkin Trans. 2 1994, 983-988.
19. C. Béguin, S. Hamman, Org. Magn. Reson. 1981, 16, 129-132
20. M. C. Salon, S. Hamman, C. G. Béguin, Org. Magn. Reson. 1983, 21, 265-270
21. M. C. Salon, S. Hamman, C. G. Béguin, J. Fluorine Chem. 1985, 27, 361-370
22. H. Ünver, E. Kendi, K. Güven, T. N. Durlu, Z. Naturforsch. B 2002, 57, 685-690.
23. D. O'Hagan, C. Bilton, J. A. K. Howard, L. Knight, D. J. Tozer, J. Chem. Soc. Perkin Trans. 2 2000, 605-607
24. C. R. S. Briggs, D. O'Hagan, J. A. K. Howard, D. S. Yufit, J. Fluorine Chem. 2003, 119, 9-13
25. C. R. S. Briggs, M. J. Allen, D. O'Hagan, D. J. Tozer, A. M. Z. Slawin, A. E. Goeta, J. A. K. Howard, Org. Biomol. Chem. 2004, 2, 732-740
26. N. E. J. Gooseman, D. O'Hagan, A. M. Z. Slawin, A. M. Teale, D. J. Tozer, R. J. Young, Chem. Commun. 2006, 3190-3192
27. N. E. J. Gooseman, D. O'Hagan, M. J. G. Peach, A. M. Z. Slawin, D. J. Tozer, R. J. Young, Angew. Chem. 2007, 119, 6008-6012
28. Angew. Chem. Int. Ed. 2007, 46, 5904-5908
29. D. Y. Buissonneaud, T. van Mourik, D. O'Hagan, Tetrahedron 2010, 66, 2196-2202
30. for an excellent review see, D. O'Hagan, Chem. Soc. Rev. 2008, 37, 308-319
31. I. Hyla-Kryspin, S. Grimme, S, Hruschka, G. Haufe, Org. Biomol. Chem. 2008, 6, 4167-4175.
32. C. Sparr, W. B. Schweizer, H. M. Senn, R. Gilmour, Angew. Chem. 2009, 121, 3111-3114
33. Angew. Chem. Int. Ed. 2009, 48, 3065-3068
34. C. Bucher, C. Sparr, W. B. Schweizer, R. Gilmour, Chem. Eur. J. 2009, 15, 7637-7647
35. C. Mondelli, C. Bucher, A. Baiker, R. Gilmour, J. Mol. Catal. A: Chem. 2010, 327, 87-91
36. C. Sparr, R. Gilmour, Angew. Chem. 2010, 122, 6670-6673
37. Angew. Chem. Int. Ed. 2010, 49, 6520-6523
38. C. Bucher, R. Gilmour, Angew. Chem. 2010, 122, 8906-8910
39. Angew. Chem. Int. Ed. 2010, 49, 8724-8728
40. S. Paul, W. B. Schweizer, M.-O. Ebert, R. Gilmour, Organometallics 2010, 29, 4424-4427.
41. L. Goodman, H. B. Gu, V. Pophristic, J. Phys. Chem. A 2005, 109, 1223-1229.
42. F. Weinhold, C. R. Landis, Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective, Cambridge University Press, Cambridge, 2005.
43. S. Sharif, M. C. Hout, P. M. Tolstoy, M. D. Toney, K. H. M. Jonsson, H.-H. Limbach, J. Phys. Chem. B 2007, 111, 3869-3876
44. M. Chan-Huot, C. Niether, S. Sharif, P. M. Tolstoy, M. D. Toney, H.-H. Limbach, J. Mol. Struct. 2010, 976, 282-289
45. M. Chan-Huot, S. Sharif, P. M. Tolstoy, M. D. Toney, H.-H. Limbach, Biochemistry 2010, 49, 10818-10830.
46. Gaussian 09, Revision A.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr. , J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, 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, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
47. Y. Zhao, D. G. Truhlar, Theor. Chem. Acc. 2008, 120, 215-241
48. Y. Zhao, D. G. Truhlar, Acc. Chem. Res. 2008, 41, 157-167.
49. B. J. Lynch, Y. Zhao, D. G. Truhlar, J. Phys. Chem. A 2003, 107, 1384-1388.