Hydrogen bonded arrays: The power of multiple hydrogen bonds

Journal of the American Chemical Society

Volumn 134, Issue 4, 2012, Pages 2094-2099

  Shokri, Alireza ^a   Schmidt, Jacob ^a   Wang, Xue Bin ^b,c   Kass, Steven R ^a  

^a University of Minnesota   (United States)

^b PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

^c WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC PROCESS; ELECTRON DETACHMENT ENERGIES; HYDROGEN BOND INTERACTION; HYDROGEN BONDED NETWORK; INTERACTION ENERGIES; MODEL COMPOUND; OH GROUP;

PHOTOELECTRON SPECTROSCOPY;

HYDROGEN BONDS;

HYDROXYL GROUP; POLYOL; WATER;

ARTICLE; CATALYSIS; CONTROLLED STUDY; ELECTRON; HYDROGEN BOND; PKA; X RAY PHOTOELECTRON SPECTROSCOPY;

ALCOHOLS; HYDROGEN BONDING; MOLECULAR STRUCTURE; QUANTUM THEORY;

EID: 84863011754     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2081907     Document Type: Article

References (52)

1. Childs, W.; Boxer, S. G. Biochemistry 2010, 49, 2725-2731
2. Simon, L.; Goodman, J. M. J. Org. Chem. 2010, 75, 1831-1840
3. Sigala, P. A.; Kraut, D. A.; Caaveiro, J. M. M.; Pybus, B.; Rubin, E. A.; Ringe, D.; Petsko, G. A.; Herschlag, D. J. Am. Chem. Soc. 2008, 130, 13696-13708
4. Zhang, Y.; Kua, J.; McCammon, J. A. J. Am. Chem. Soc. 2002, 124, 10572-10577
5. Whiting, A. K.; Peticolas, W. L. Biochemistry 1994, 33, 552-561
6. Gerlt, J. A.; Gassman, P. G. Biochemistry 1993, 32, 11943-11952
7. Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552-11568
8. Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887-1890
9. Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927-1930
10. Cleland, W. W.; Frey, P. A.; Gerlt, J. A. J. Biol. Chem. 1998, 273, 25529-25532
11. Schwans, J. P.; Kraut, D. A.; Herschlag, D. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 14271-14275
12. Shan, S. O.; Herschlag, D. Proc. Natl. Acad. Sci. U. S. A. 1996, 93, 14474-14479
13. Shan, S. O.; Herschlag, D. J. Am. Chem. Soc. 1996, 118, 5515-5518
14. Shan, S. O.; Loh, S.; Herschlag, D. Science 1996, 272, 97-101
15. Shan, S. O.; Herschlag, D. Methods Enzymol. 1999, 308, 246-276
16. Tian, Z.; Fattahi, A.; Lis, L.; Kass, S. R. J. Am. Chem. Soc. 2009, 131, 16984-16988
17. Jencks, W. P. Adv. Enzymol. Relat. Areas Mol. Biol. 1975, 43, 219-410
18. Jencks, W. P. Methods Enzymol. 1989, 171, 145-164
19. Wang, X. B.; Wang, L. S. Rev. Sci. Instrum. 2008, 79, 073108
20. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
21. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
22. Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007-1023
23. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2008, 112, 1095-1099
24. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
25. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157-167
26. Papajak, E.; Truhlar, D. G. J. Chem. Theory Comput. 2010, 6, 597-601
27. Frisch, M. J.,. Gaussian 09; Gaussian, Inc.: Pittsburgh, PA, 2009.
28. Woolley, E. M.; Tomkins, J.; Hepler, L. G. J. Solution Chem. 1972, 1, 341-351
29. Ellison, G. B.; Engleking, P. C.; Lineberger, W. C. J. Phys. Chem. 1982, 86, 4873-4878
30. Tian, Z.; Fattahi, A.; Lis, L.; Kass, S. R. Croat. Chem. Acta 2009, 82, 41-45
31. Meot-Ner (Mautner), M. Chem. Rev. 2005, 105, 213-284
32. Meot-Ner (Mautner), M.; Speller, C. V. J. Phys. Chem. 1986, 90, 6616-6624
33. Lu, Z.; Continetti, R. E. J. Phys. Chem. A 2004, 108, 9962-9969
34. Berzinsh, U.; Gustafsson, M.; Hanstorp, D.; Klinkmuller, A.; Ljungblad, U.; Martensson-Pendrill, A. M. Phys. Rev. A 1995, 51, 231-238
35. Weaver, A.; Arnold, D. W.; Bradforth, S. E.; Neumark, D. M. J. Chem. Phys. 1991, 94, 1740-1751
36. Wang, X. B.; Wang, L. S. J. Chem. Phys. 2000, 113, 10928-10933
37. Wang, X. B.; Vorpagel, E. R.; Yang, X.; Wang, L. S. J. Phys. Chem. A 2001, 105, 10468-10474
38. Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1986, 108, 6189-6197
39. Wu, R.; McMahon, T. B. J. Phys. Chem. B 2009, 113, 8767-8775
40. Wu, R.; McMahon, T. B. J. Am. Chem. Soc. 2007, 129, 11312-11313
41. Norrman, K.; McMahon, T. B. J. Phys. Chem. A 1999, 103, 7008-7016
42. Meot-Ner (Mautner), M.; Sieck, L. W.; Scheiner, S.; Duan, X. J. Am. Chem. Soc. 1994, 116, 7848-7856
43. Campbell, S.; Rodgers, M. T.; Marzluff, E. M.; Beauchamp, J. L. J. Am. Chem. Soc. 1995, 117, 12840-12854
44. Sharma, R. B.; Blades, A. T.; Kebarle, P. J. Am. Chem. Soc. 1984, 106, 510-516
45. Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1983, 105, 4906-4911
46. Xantheas, S. S. J. Am. Chem. Soc. 1995, 117, 10373-10380
47. Bruice, T. C.; Pandit, U. K. Proc. Natl. Acad. Sci. U.S.A. 1960, 46, 402-404
48. -1 in the transition structure. For more details, see: Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1988, 110, 3075-3080
49. Joyce, L. A.; Shabbir, S. H.; Anslyn, E. V. Chem. Soc. Rev. 2010, 39, 3621-3632
50. Takemoto, Y. Yuki Gosei Kagaku Kyokaishi 2006, 64, 1139-1147
51. Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289-296
52. Betschmann, P.; Lerner, C.; Sahli, S.; Obst, U.; Diederich, F. Chimia 2000, 54, 633-639