How strong is the C(α)-H···O=C hydrogen bond?

Journal of the American Chemical Society

Volumn 122, Issue 19, 2000, Pages 4750-4755

  Vargas, Rubicelia ^a,b   Garza, Jorge ^a,b   Dixon, David A ^a   Hay, Benjamin P ^a  

^a PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

^b UNIVERSIDAD AUTÓNOMA METROPOLITANA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; ENERGY; GEOMETRY; HYDROGEN BOND; PROTEIN CONFORMATION; PROTEIN STRUCTURE; THERMODYNAMICS;

EID: 0034679011     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993600a     Document Type: Article

References (94)

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66. Examples of each dimer: (a) 1: Ray, M.; Golombek, A. P.; Hendrich, M. P.; Young, V. G.; Borovik, A. S. J. Am. Chem. Soc. 1996, 118, 6084. (b) 2: Raper, E. S.; Britton, A. M.; Creighton, J. R.; Clegg, W.; Hooper, M.; Kubiak, M. Acta Crystallogr., Sect. C 1987 43, 1538. (c) 3, Wenkert, E.; Moeller, P. D. R.; Piettre, S. R.; McPhail, A. T. J. Org. Chem. 1987, 52, 3404. (d) 4, Oliver, J. E.; Waters, R. M.; Lusby, W. R.; Flippen- Anderson, J. L. J. Heterocycl. Chem. 1991, 28, 1569. (e) Structure of neat DMF: Borrman, H.; Persson, I.; Sandström, M.; Stalhandske, C. M. V. J. Chem. Soc., Perkin Trans. 2 2000, 393.
67. Examples of each dimer: (a) 1: Ray, M.; Golombek, A. P.; Hendrich, M. P.; Young, V. G.; Borovik, A. S. J. Am. Chem. Soc. 1996, 118, 6084. (b) 2: Raper, E. S.; Britton, A. M.; Creighton, J. R.; Clegg, W.; Hooper, M.; Kubiak, M. Acta Crystallogr., Sect. C 1987 43, 1538. (c) 3, Wenkert, E.; Moeller, P. D. R.; Piettre, S. R.; McPhail, A. T. J. Org. Chem. 1987, 52, 3404. (d) 4, Oliver, J. E.; Waters, R. M.; Lusby, W. R.; Flippen- Anderson, J. L. J. Heterocycl. Chem. 1991, 28, 1569. (e) Structure of neat DMF: Borrman, H.; Persson, I.; Sandström, M.; Stalhandske, C. M. V. J. Chem. Soc., Perkin Trans. 2 2000, 393.
68. Examples of each dimer: (a) 1: Ray, M.; Golombek, A. P.; Hendrich, M. P.; Young, V. G.; Borovik, A. S. J. Am. Chem. Soc. 1996, 118, 6084. (b) 2: Raper, E. S.; Britton, A. M.; Creighton, J. R.; Clegg, W.; Hooper, M.; Kubiak, M. Acta Crystallogr., Sect. C 1987 43, 1538. (c) 3, Wenkert, E.; Moeller, P. D. R.; Piettre, S. R.; McPhail, A. T. J. Org. Chem. 1987, 52, 3404. (d) 4, Oliver, J. E.; Waters, R. M.; Lusby, W. R.; Flippen- Anderson, J. L. J. Heterocycl. Chem. 1991, 28, 1569. (e) Structure of neat DMF: Borrman, H.; Persson, I.; Sandström, M.; Stalhandske, C. M. V. J. Chem. Soc., Perkin Trans. 2 2000, 393.
69. Examples of each dimer: (a) 1: Ray, M.; Golombek, A. P.; Hendrich, M. P.; Young, V. G.; Borovik, A. S. J. Am. Chem. Soc. 1996, 118, 6084. (b) 2: Raper, E. S.; Britton, A. M.; Creighton, J. R.; Clegg, W.; Hooper, M.; Kubiak, M. Acta Crystallogr., Sect. C 1987 43, 1538. (c) 3, Wenkert, E.; Moeller, P. D. R.; Piettre, S. R.; McPhail, A. T. J. Org. Chem. 1987, 52, 3404. (d) 4, Oliver, J. E.; Waters, R. M.; Lusby, W. R.; Flippen-Anderson, J. L. J. Heterocycl. Chem. 1991, 28, 1569. (e) Structure of neat DMF: Borrman, H.; Persson, I.; Sandström, M.; Stalhandske, C. M. V. J. Chem. Soc., Perkin Trans. 2 2000, 393.
70. Examples of each dimer: (a) 1: Ray, M.; Golombek, A. P.; Hendrich, M. P.; Young, V. G.; Borovik, A. S. J. Am. Chem. Soc. 1996, 118, 6084. (b) 2: Raper, E. S.; Britton, A. M.; Creighton, J. R.; Clegg, W.; Hooper, M.; Kubiak, M. Acta Crystallogr., Sect. C 1987 43, 1538. (c) 3, Wenkert, E.; Moeller, P. D. R.; Piettre, S. R.; McPhail, A. T. J. Org. Chem. 1987, 52, 3404. (d) 4, Oliver, J. E.; Waters, R. M.; Lusby, W. R.; Flippen- Anderson, J. L. J. Heterocycl. Chem. 1991, 28, 1569. (e) Structure of neat DMF: Borrman, H.; Persson, I.; Sandström, M.; Stalhandske, C. M. V. J. Chem. Soc., Perkin Trans. 2 2000, 393.
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76. Values obtained at the MP2/6-31++G(2d, 2p) level with BSSE correction: Rovira, M. C.; Novoa, J. J.; Whangbo, M.-H.; Williams, J. M. Chem. Phys. 1995, 200, 319.
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81. Values for C-H⋯Q=C hydrogen bonds obtained at lower levels of theory also fall within this range: (a) Turi, L.; Dannenberg, J. J. J. Phys. Chem. 1993, 97, 12197. (b) Turi, L.; Dannenberg, J. J. J. Phys. Chem. 1996, 100, 9638. (c) Cardenas-Jiron, G. I.; Masunov, A.; Dannenberg, J. J. J. Phys. Chem. 1999, 103, 7042.
82. Values for C-H⋯Q=C hydrogen bonds obtained at lower levels of theory also fall within this range: (a) Turi, L.; Dannenberg, J. J. J. Phys. Chem. 1993, 97, 12197. (b) Turi, L.; Dannenberg, J. J. J. Phys. Chem. 1996, 100, 9638. (c) Cardenas-Jiron, G. I.; Masunov, A.; Dannenberg, J. J. J. Phys. Chem. 1999, 103, 7042.
83. Values for C-H⋯Q=C hydrogen bonds obtained at lower levels of theory also fall within this range: (a) Turi, L.; Dannenberg, J. J. J. Phys. Chem. 1993, 97, 12197. (b) Turi, L.; Dannenberg, J. J. J. Phys. Chem. 1996, 100, 9638. (c) Cardenas-Jiron, G. I.; Masunov, A.; Dannenberg, J. J. J. Phys. Chem. 1999, 103, 7042.
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86. -1): (a) Methane 418.0 ± 3.5, fluoromethane 409.0 ± 4.0, difluoromethane 389 ± 3.5, trifluoromethane 376.0 ± 4.5, ethylene 407.0 ± 3.0: Graul, S. T.; Squires, R. R. J. Am. Chem. Soc. 1990,112, 2517. (b) Ethane 420.1 ± 2.0: DePuy, C. H.; Gronert, S.; Barlow, S. E.; Bierbaum, V. M.; Damrauer, R. J. Am. Chem. Soc. 1990, 112, 2517. (c) Benzene 401.7 ± 0.5: Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590. (d) Acetylene 378.0 ± 0.7: Ervin, K. M.; Gronert, S.; Barlow, S. E.; Gilles, M. K.; Harrison, A. G.; Bierbaum, V. M.; DePuy, C. H.; Lin, W. C. J. Am. Chem. Soc. 1990, 112, 5750. (e) Acetal 389.8 ± 0.9: Nimlos, M. R.; Soderquist, J. A.; Ellison, G. B. J. Am. Chem. Soc. 1989, 111, 7675. (f) Hydrogen cyanide 348.3 ± 2.0: Bradforth, S. E.; Kim, E. H.; Arnold, D. W.; Neumark, D. M. J. Chem. Phys. 1993, 98, 800.
87. -1): (a) Methane 418.0 ± 3.5, fluoromethane 409.0 ± 4.0, difluoromethane 389 ± 3.5, trifluoromethane 376.0 ± 4.5, ethylene 407.0 ± 3.0: Graul, S. T.; Squires, R. R. J. Am. Chem. Soc. 1990,112, 2517. (b) Ethane 420.1 ± 2.0: DePuy, C. H.; Gronert, S.; Barlow, S. E.; Bierbaum, V. M.; Damrauer, R. J. Am. Chem. Soc. 1990, 112, 2517. (c) Benzene 401.7 ± 0.5: Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590. (d) Acetylene 378.0 ± 0.7: Ervin, K. M.; Gronert, S.; Barlow, S. E.; Gilles, M. K.; Harrison, A. G.; Bierbaum, V. M.; DePuy, C. H.; Lin, W. C. J. Am. Chem. Soc. 1990, 112, 5750. (e) Acetal 389.8 ± 0.9: Nimlos, M. R.; Soderquist, J. A.; Ellison, G. B. J. Am. Chem. Soc. 1989, 111, 7675. (f) Hydrogen cyanide 348.3 ± 2.0: Bradforth, S. E.; Kim, E. H.; Arnold, D. W.; Neumark, D. M. J. Chem. Phys. 1993, 98, 800.
88. -1): (a) Methane 418.0 ± 3.5, fluoromethane 409.0 ± 4.0, difluoromethane 389 ± 3.5, trifluoromethane 376.0 ± 4.5, ethylene 407.0 ± 3.0: Graul, S. T.; Squires, R. R. J. Am. Chem. Soc. 1990,112, 2517. (b) Ethane 420.1 ± 2.0: DePuy, C. H.; Gronert, S.; Barlow, S. E.; Bierbaum, V. M.; Damrauer, R. J. Am. Chem. Soc. 1990, 112, 2517. (c) Benzene 401.7 ± 0.5: Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590. (d) Acetylene 378.0 ± 0.7: Ervin, K. M.; Gronert, S.; Barlow, S. E.; Gilles, M. K.; Harrison, A. G.; Bierbaum, V. M.; DePuy, C. H.; Lin, W. C. J. Am. Chem. Soc. 1990, 112, 5750. (e) Acetal 389.8 ± 0.9: Nimlos, M. R.; Soderquist, J. A.; Ellison, G. B. J. Am. Chem. Soc. 1989, 111, 7675. (f) Hydrogen cyanide 348.3 ± 2.0: Bradforth, S. E.; Kim, E. H.; Arnold, D. W.; Neumark, D. M. J. Chem. Phys. 1993, 98, 800.
89. -1): (a) Methane 418.0 ± 3.5, fluoromethane 409.0 ± 4.0, difluoromethane 389 ± 3.5, trifluoromethane 376.0 ± 4.5, ethylene 407.0 ± 3.0: Graul, S. T.; Squires, R. R. J. Am. Chem. Soc. 1990,112, 2517. (b) Ethane 420.1 ± 2.0: DePuy, C. H.; Gronert, S.; Barlow, S. E.; Bierbaum, V. M.; Damrauer, R. J. Am. Chem. Soc. 1990, 112, 2517. (c) Benzene 401.7 ± 0.5: Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590. (d) Acetylene 378.0 ± 0.7: Ervin, K. M.; Gronert, S.; Barlow, S. E.; Gilles, M. K.; Harrison, A. G.; Bierbaum, V. M.; DePuy, C. H.; Lin, W. C. J. Am. Chem. Soc. 1990, 112, 5750. (e) Acetal 389.8 ± 0.9: Nimlos, M. R.; Soderquist, J. A.; Ellison, G. B. J. Am. Chem. Soc. 1989, 111, 7675. (f) Hydrogen cyanide 348.3 ± 2.0: Bradforth, S. E.; Kim, E. H.; Arnold, D. W.; Neumark, D. M. J. Chem. Phys. 1993, 98, 800.
90. -1): (a) Methane 418.0 ± 3.5, fluoromethane 409.0 ± 4.0, difluoromethane 389 ± 3.5, trifluoromethane 376.0 ± 4.5, ethylene 407.0 ± 3.0: Graul, S. T.; Squires, R. R. J. Am. Chem. Soc. 1990,112, 2517. (b) Ethane 420.1 ± 2.0: DePuy, C. H.; Gronert, S.; Barlow, S. E.; Bierbaum, V. M.; Damrauer, R. J. Am. Chem. Soc. 1990, 112, 2517. (c) Benzene 401.7 ± 0.5: Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590. (d) Acetylene 378.0 ± 0.7: Ervin, K. M.; Gronert, S.; Barlow, S. E.; Gilles, M. K.; Harrison, A. G.; Bierbaum, V. M.; DePuy, C. H.; Lin, W. C. J. Am. Chem. Soc. 1990, 112, 5750. (e) Acetal 389.8 ± 0.9: Nimlos, M. R.; Soderquist, J. A.; Ellison, G. B. J. Am. Chem. Soc. 1989, 111, 7675. (f) Hydrogen cyanide 348.3 ± 2.0: Bradforth, S. E.; Kim, E. H.; Arnold, D. W.; Neumark, D. M. J. Chem. Phys. 1993, 98, 800.
91. -1): (a) Methane 418.0 ± 3.5, fluoromethane 409.0 ± 4.0, difluoromethane 389 ± 3.5, trifluoromethane 376.0 ± 4.5, ethylene 407.0 ± 3.0: Graul, S. T.; Squires, R. R. J. Am. Chem. Soc. 1990,112, 2517. (b) Ethane 420.1 ± 2.0: DePuy, C. H.; Gronert, S.; Barlow, S. E.; Bierbaum, V. M.; Damrauer, R. J. Am. Chem. Soc. 1990, 112, 2517. (c) Benzene 401.7 ± 0.5: Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590. (d) Acetylene 378.0 ± 0.7: Ervin, K. M.; Gronert, S.; Barlow, S. E.; Gilles, M. K.; Harrison, A. G.; Bierbaum, V. M.; DePuy, C. H.; Lin, W. C. J. Am. Chem. Soc. 1990, 112, 5750. (e) Acetal 389.8 ± 0.9: Nimlos, M. R.; Soderquist, J. A.; Ellison, G. B. J. Am. Chem. Soc. 1989, 111, 7675. (f) Hydrogen cyanide 348.3 ± 2.0: Bradforth, S. E.; Kim, E. H.; Arnold, D. W.; Neumark, D. M. J. Chem. Phys. 1993, 98, 800.
92. -1): (a) Acetone 369.1 ± 2.1 from: Bartmess, J. E.; Scott, J. A.; Mclver, R. T., Jr. J. Am. Chem. Soc. 1979, 101, 6047. (b) Acetylacetone 343.8 ± 2.1 from: Taft, R. W.; Bordwell, F. G. Acc. Chem. Res. 1988, 21, 463.
93. -1): (a) Acetone 369.1 ± 2.1 from: Bartmess, J. E.; Scott, J. A.; Mclver, R. T., Jr. J. Am. Chem. Soc. 1979, 101, 6047. (b) Acetylacetone 343.8 ± 2.1 from: Taft, R. W.; Bordwell, F. G. Acc. Chem. Res. 1988, 21, 463.
94. Dixon, D. A.; Dobbs, K. D.; Valentini, J. J. J. Phys. Chem. 1994, 98, 13435.