Dihydrogen bonding: Structures, energetics, and dynamics

Chemical Reviews

Volumn 101, Issue 7, 2001, Pages 1963-1980

  Custelcean, Radu ^a   Jackson, James E ^b  

^a University of Minnesota   (United States)

^b MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROGEN BONDING;

CATALYST SELECTIVITY; HYDRIDES; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; SOLUTIONS; TRANSITION METAL COMPOUNDS;

HYDROGEN BONDS;

HYDROGEN;

CHEMISTRY; HYDROGEN BOND; PHYSICAL CHEMISTRY; REVIEW;

CHEMISTRY, PHYSICAL; HYDROGEN; HYDROGEN BONDING;

EID: 0035385141     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr000021b     Document Type: Review

References (104)

1. Jeffrey, G.A. An Introduction to Hydrogen Bonding; Oxford University Press: Oxford, 1997.
2. Jeffrey, G.A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991.
3. Calhorda, M.J. Chem. Commun. 2000, 801.
4. Shubina, E.S.; Belkova, N.V.; Epstein, L.M. J. Organomet. Chem. 1997, 536-537, 17.
5. Crabtree, R.H.; Siegbahn, P.E.M.; Eisenstein, O.; Rheingold, A.L.; Koetzle, T.F. Acc. Chem. Res. 1996, 29, 348.
6. Crabtree, R.H. J. Organomet. Chem. 1998, 577, 111.
7. Alkorta, I.; Rozas, I.; Elguero, J. Chem. Soc. Rev. 1998, 27, 163.
8. Crabtree, R.H. Science 1998, 282, 2000.
9. Crabtree, R.H.; Eisenstein, O.; Sini, G.; Peris, E. J. Organomet. Chem. 1998, 567, 7.
10. Kelly, P.; Loza, M. Chem. Britain 1999, 35, 26.
11. Zachariasen, W.H.; Mooney, R.C.L. J. Chem. Phys. 1934, 2, 34.
12. We have recently redetermined the crystal structure of ammonium hypophosphite at higher resolution, which allowed us to locate the H atoms and thus probe the existence of dihydrogen bonding. However, we found no close H⋯H contacts in this salt. Stein, R.; Custelcean, R.; Jackson, J.E., manuscript in preparation.
13. Burg, A.B. Inorg. Chem. 1964, 3, 1325.
14. Titov, L.V.; Makarova, M.D.; Rosolovskii, V.Y. Dokl. Akad. Nauk 1968, 180, 381.
15. Brown, M.P.; Heseltine, R.W. Chem. Commun. 1968, 1551.
16. Brown, M.P.; Heseltine, R.W.; Smith, P.A.; Walker, P.J. J. Chem. Soc. A 1970, 410.
17. Brown, M.P.; Walker, P.J. Spectrochim. Acta 1974, 30A, 1125.
18. Shubina, E.S.; Bachmutova, E.V.; Saitkulova, L.N.; Epstein, L.M. Mendeleev Commun. 1997, 83.
19. Epstein, L.M.; Shubina, E.S.; Bakhmutova, E.V.; Saitkulova, L.N.; Bakhmutov, V.I.; Chistyakov, A.L.; Stankevich, I.V. Inorg. Chem. 1998, 37, 3013.
20. Shubina, E.S.; Belkova, N.V.; Bakhmutova, E.V.; Saitkulova, L.N.; Ionidis, A.V.; Epstein, L.M. Russ. Chem. Bull. 1998, 47, 817.
21. Jackson, J.E.; Huang, R.; Eckert, J.; Sharma, M.; Argyriou, D.; Sheldon, R., manuscript in preparation.
22. Richardson, T.B.; de Gala, S.; Crabtree, R.H.; Siegbhan, P.E.M. J. Am. Chem. Soc. 1995, 117, 12875.
23. Cramer, C.J.; Gladfelter, W.L. Inorg. Chem. 1997, 36, 5358.
24. Klooster, W.T.; Koetzle, T.F.; Siegbahn, P.E.M.; Richardson, T.B.; Crabtree, R.H. J. Am. Chem. Soc. 1999, 121, 6337.
25. Popelier, P.L.A. J. Phys. Chem. A 1998, 102, 1873.
26. Nöth, H.; Thomas, S. Eur. J. Inorg. Chem. 1999, 1373.
27. Zottola, M.A.; Pedersen, L.G.; Singh, P.; Shaw, B.R. Modeling the Hydrogen Bond; Smith,D.A., Ed.; ACS Symposium Series: American Chemical Society, Washington, DC, 1994; Vol. 569, pp 277-285.
28. Singh, P.; Zottola, M.; Huang, S.; Shaw, B.R.; Pedersen, L.G. Acta Crystallogr. 1996, C52, 693.
29. Padilla-Martińez, I.R.; Rosalez-Hoz, M. De J.; Tlahuext, H.; Camacho-Camacho, C.; Ariza-Castolo, A.; Contreras, R. Chem. Ber. 1996, 129, 441.
30. This number was obtained using the value of 1.45 Å as the van der Waals radius for the hydridic hydrogen.
31. Flores-Parra, A.; Sánchez-Ruiz, S.A.; Guadarrama, C.; Nöth, H.; Contreras, R. Eur. J. Inorg. Chem. 1999, 2069.
32. Atwood, J.L.; Koutsantonis, G.A.; Lee, F.-C.; Raston, C.L. Chem. Commun. 1994, 91.
33. Campbell, J.P.; Hwang, J.W.; Young, V.G.; Von Dreele, R.B.; Cramer, C.J.; Gladfelter, W.L.J. Am. Chem. Soc. 1998, 120, 521.
34. Liu, Q.; Hoffmann, R. J. Am. Chem. Soc. 1995, 117, 10108.
35. Alkorta, I.; Elguero, J.; Foces-Foces, C. Chem. Commun. 1996, 1633.
36. Remko, M. Mol. Phys. 1998, 94, 839.
37. Kulkarni, S.A. J. Phys. Chem. A 1998, 102, 7704.
38. Kulkarni, S.A.; Srivastava, A.K. J. Phys. Chem. A 1999, 103, 2836.
39. Lundell, J.; Pettersson, M. Phys. Chem. Chem. Phys. 1999, 1, 1601.
40. Grabowski, S. J. Chem. Phys. Lett. 1999, 312 (5-6), 542.
41. Grabowski, S.J. J. Phys. Chem. 2000, 104, 5551.
42. Milstein, D.; Calabrese, J.C.; Williams, I.D. J. Am. Chem. Soc. 1986, 108, 6387.
43. Stevens, R.C.; Bau, R.; Milstein, D.; Blum, O.; Koetzle,T.F.J. Chem. Soc., Dalton Trans. 1990, 1429.
44. Feracin, S.; Bürgi, T.; Bakhmutov, V.I.; Eremenko, I.; Vorontsov, E.V.; Vimenits, A.B.; Berke, H. Organometallics 1994, 13, 4194.
45. Lee, J.C.; Rheingold, A.L.; Muller, B.; Pregosin, P.S.; Crabtree, R.H. Chem. Commun. 1994, 1021.
46. Peris, E.; Lee, J.C.; Rambo, J.R., Eisenstein, O.; Crabtree, R.H. J. Am. Chem. Soc. 1995, 117, 3485.
47. Lough, A.J.; Park, S.; Ramachandran, R.; Morris, R.H. J. Am. Chem. Soc. 1994, 116, 8356.
48. Park, S.; Ramachandran, R.; Lough, A.J.; Morris, R.H. Chem. Commun. 1994, 2201.
49. Park, S.; Lough, A.J.; Morris, R.H. Inorg. Chem. 1996, 35, 3001.
50. Wessel, J.; Lee, J.C.; Peris, E.; Yap, G.P.A.; Fortin, J.B.; Ricci, J.S.; Sini, G.; Albinati, A.; Koetzle, T.F.; Eisenstein, O.; Rheingold, A.L.; Crabtree, R.H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2507.
51. Patel, B.P.; Wessel, J.; Yao, W.; Lee, J.C. Jr.; Peris, E.; Koetzle, T.F.; Yap, G.P.A.; Fortin, J.B.; Ricci, J.S.; Sini, G.; Albinati, A.; Eisenstein, O.; Rheingold, A.L.; Crabtree, R.H. New J. Chem. 1997, 21, 413.
52. Sini, G.; Eisenstein, O.; Yao, W.; Crabtree, R.H. Inorg. Chim. Acta 1998, 280, 26.
53. Patel, B.P.; Yao, W.; Yap, G.P.A.; Rheingold, A.L.; Crabtree, R.H. Chem. Commun. 1996, 991.
54. Peris, E.; Wessel, J.; Patel, B.P.; Crabtree, R.H. Chem. Commun. 1995, 2175.
55. Desmurs, P.; Kavallieratos, K.; Yao, W.; Crabtree, R.H. New J. Chem. 1999, 23, 1111.
56. Shubina, E.S.; Belkova, N.V.; Krylov, A.N.; Vorontsov, E.V.; Epstein, L.M.; Gusev, D.G.; Niedermann, M.; Berke, H. J. Am. Chem. Soc. 1996, 118, 1105.
57. Belkova, N.V.; Shubina, E.S.; Ionidis, A.V.; Epstein, L.M.; Jacobsen, H.; Messmer, A.; Berke, H. Inorg. Chem. 1997, 36, 1522.
58. Messmer, A.; Jacobsen, H.; Berke, H. Chem. Eur. J. 1999, 5, 3341.
59. Scheiner, S.; Orlova, G. J. Phys. Chem. A 1998, 102, 260.
60. Richardson, T.B.; Koetzle, T.F.; Crabtree, R.H. Inorg. Chim. Acta 1996, 250, 69.
61. Xu, W.; Lough, A.J.; Morris, R.H. Can. J. Chem. 1997, 75, 475.
62. Huang, L.-Y.; Aulwurm, U.R.; Heinemann, F.W.; Knoch, F.; Kisch, H. Chem. Eur. J. 1998, 4, 1641.
63. Junk, P.C.; Steed, J.W. J. Organomet. Chem. 1999, 587, 191.
64. Braga, D.; De Leonardis, P.; Grepioni, F.; Tedesco, E.; Calhorda, M.J. Inorg. Chem. 1998, 37, 3337.
65. Custelcean, R.; Jackson, J.E., unpublished results.
66. Abramov, Y.A.; Brammer, L.; Klooster, W.T.; Bullock, R.M. Inorg. Chem. 1998, 37, 6317.
67. Gusev, D.G.; Lough, A.J.; Morris, R.H. J. Am. Chem. Soc. 1998, 120, 13138.
68. Abdur-Rashid, K.; Gusev, D.G.; Landau, S.E.; Lough, A.J.; Morris, R.H. J. Am. Chem. Soc. 1998, 120, 11826.
69. Abdur-Rashid, K.; Gusev, D.G.; Lough, A.J.; Morris, R.H. Organometallics 2000, 19, 834.
70. Jackson, J.E.; Bass, S.; Huang, R., unpublished results.
71. Custelcean, R.; Jackson, J.E. Angew. Chem., Int. Ed. Engl. 1999, 38, 1661.
72. Custelcean, R.; Jackson, J.E. J. Am. Chem. Soc. 1998, 120, 12935.
73. Lee, J.C.; Peris, E.; Rheingold, A.L.; Crabtree, R.H. J. Am. Chem. Soc. 1994, 116, 11014.
74. Ayllón, J.A.; Gervaux, C.; Sabo-Etienne, S.; Chaudret, B. Organometallics 1997, 16, 2000.
75. Orlova, G.; Scheiner, S.; Kar, T. J. Phys. Chem. A 1999, 103, 514.
76. Shubina, E.S.; Belkova, N.V.; Bakhmutova, E.V.; Vorontsov, E.V.; Bakhmutov, V.I.; Ionidis, A.V.; Bianchini, C.; Marvelli, L.; Peruzzini, M.; Epstein, L.M. Inorg. Chim. Acta 1998, 280, 302.
77. Epstein, L.M.; Shubina, E.S. Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 359.
78. Orlova, G.; Scheiner, S. J. Phys. Chem. A 1998, 102, 4813.
79. Chu, H.S.; Xu, Z.; Ng, S.M.; Lau, C.P.; Lin, Z. Eur. J. Inorg. Chem. 2000, 993.
80. Ayllón, J.A.; Sabo-Etienne, S.; Chaudret, B.; Ulrich, S.; Limbach, H.-H. Inorg. Chim. Acta 1997, 259, 1.
81. Gründemann, S.; Ulrich, S.; Limbach, H.-H.; Golubev, N.S.; Denisov, G.S.; Epstein, L.M.; Sabo-Etienne, S.; Chaudret, B. Inorg. Chem. 1999, 38, 2550.
82. Chu, H.S.; Lau, C.P.; Wong, K.Y.; Wong, W.T. Organometallics 1998, 17, 2768.
83. Musashi, Y.; Sakaki, S. J. Am. Chem. Soc. 2000, 122, 3867.
84. Ayllón, J.A.; Sayers, S.F.; Sabo-Etienne, S.; Donnadieu, B.; Chaudret, B. Organometallics 1999, 18, 3981.
85. Caballero, A.; Jalón, F.A.; Manzano, B.R. Chem. Commun. 1998, 1879.
86. Patel, B.P.; Kavallieratos, K.; Crabtree, R.H. J. Organomet. Chem. 1997, 528, 205.
87. Bosque, R.; Maseras, F.; Eisenstein, O.; Patel, B.P.; Yao, W.; Crabtree, R.H. Inorg. Chem. 1997, 36, 5505.
88. Yao, W.; Crabtree, R.H. Inorg. Chem. 1996, 35, 3007.
89. Aime, S.; Gobetto, R.; Valls, E. Organometallics 1997, 16, 5140.
90. Aime, S.; Férriz, M.; Gobetto, R.; Valls, E. Organometallics 1999, 18, 2030.
91. Aime, S.; Férriz, M.; Gobetto, R.; Valls, E. Organometallics 2000, 19, 707.
92. Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285.
93. Gatling, S.C.; Jackson, J.E. J. Am. Chem. Soc. 1999, 121, 8655.
94. Davis, R.E. J. Am. Chem. Soc. 1962, 84, 892.
95. Kreevoy, M.M.; Hutchins, J.E.C. J. Am. Chem. Soc. 1969, 91, 4329.
96. Pepperberg, I.M.; Halgren, T.A.; Lipscomb, W.N. J. Am. Chem. Soc. 1976, 98, 3442.
97. Mesmer, R.E.; Jolly, W.L. Inorg. Chem. 1962, 1, 608.
98. Schreiner, P.R.; Schaefer, H.F.; Schleyer, P.v.R. J. Chem. Phys. 1994, 101, 7625.
99. Watts, J.D.; Bartlett, R.J. J. Am. Chem. Soc. 1995, 117, 825.
100. Custelcean, R. J. Mol. Struct. Theochem. 2000, 505, 95.
101. Rozas, I.; Alkorta, I.; Elguero, J. Chem. Phys. Lett. 1997, 275, 423.
102. Hwang, J.-W.; Campbell, J.P.; Kozubowski, J.; Hanson, S.A.; Evans, J.F.; Gladfelter, W.L. Chem. Mater. 1995, 7, 517.
103. Custelcean, R.; Jackson, J.E. J. Am. Chem. Soc. 2000, 122, 5251.
104. Custelcean, R.; Vlassa, M.; Jackson, J.E. Angew. Chem., Int. Ed. 2000, 39, 3299.