Hydrogen-bonded complexes of methanol and acetylides. Structure and energy correlations

Journal of the American Chemical Society

Volumn 122, Issue 22, 2000, Pages 5371-5378

  Chabinyc, Michael L ^a   Brauman, John I ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; METHANOL;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENERGY TRANSFER; HYDROGEN BOND; MOLECULAR STABILITY;

EID: 0034616812     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994191l     Document Type: Article

References (92)

1. Kebarle, P. Annu. Rev. Phys. Chem. 1977, 28, 445-476.
2. Perrin, C. L.; Nielson, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511-544.
3. Meot-Ner, M. J. Am. Chem. Soc. 1984, 106, 1257-1264.
4. Meot-Ner, M.; Sieck, L. W. J. Phys. Chem. 1985, 89, 5222-5225.
5. Meot-Ner, M.; Sieck, L. W.; Koretke, K. K.; Deakyne, C. A. J. Am. Chem. Soc. 1997, 119, 10430-10438.
6. Takashima, K.; Riveros, J. M. Mass Spectrom. Rev. 1998, 17, 409-430.
7. Eigen, M. Angew. Chem., Int. Ed. Engl. 1964, 3, 1-19.
8. Jencks, W. P. Catalysis in Chemistry and Enzymology; Dover Publications: New York, 1987.
9. Bartmess, J. E. In NIST Chemistry WebBook, NIST Standard Reference Database 69; Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, 1998.
10. Cao, H. Z.; Allavena, M.; Tapia, O.; Evleth, E. M. J. Phys. Chem. 1985, 89, 1581-1592.
11. Scheiner, S. Hydrogen Bonding: A Theoretical Perspective; Oxford University Press: Oxford, 1997.
12. Kresge, A. J.; Powell, M. F. J. Org. Chem. 1986, 51, 822-824.
13. Ervin, K. M.; et al. J. Am. Chem. Soc. 1990, 112, 5750-5759.
14. -1. The reaction efficiency is 0.30 based on the Su-Chesnavich capture rate C. DePuy, personal communication.
15. Caldwell, G.; Rozeboom, M. D.; Kiplinger, J. P.; Bartmess, J. E. J. Am. Chem. Soc. 1984, 106, 4660-4667.
16. Meot-Ner, M. J. Am. Chem. Soc. 1988, 110, 3858-3862.
17. Chabinyc, M. L.; Brauman, J. I. J. Phys. Chem. A 1999, 103, 9163-9166.
18. Larson, J. W.; McMahon, T. B. J. Am. Chem. Soc. 1983, 105, 2944-2950.
19. Vogel, A. I. Practical Organic Chemistry; John Wiley & Sons Inc.: New York, 1956.
20. Hanst, P. L.; Calvert, J. G. J. Phys. Chem. 1959, 63, 104-111.
21. Zhong, M.; Brauman, J. I. J. Am. Chem. Soc. 1996, 118, 636-641.
22. Han, C.-C.; Brauman, J. I. J. Am. Chem. Soc. 1989, 111, 6491-6496.
23. DePuy, C.; Grabowski, J. J.; Bierbaum, V. M.; Ingemann, S.; Nibbering, N. M. M. J. Am. Chem. Soc. 1985, 107, 1093-1098.
24. Blair, L. K.; Isolani, P. C.; Riveros, J. M. J. Am. Chem. Soc. 1973, 95, 1057-1060.
25. DePuy, C. H.; Bierbaum, V. M. J. Am. Chem. Soc. 1981, 103, 5034-5038.
26. Bartmess, J. E.; Scott, J. A.; Mclver, R. T., Jr. J. Am. Chem. Soc. 1979, 101, 6056-6063.
27. Hansch, C. H.; Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology; John Wiley & Sons: New York, 1979.
28. Farneth, W. E.; Brauman, J. I. J. Am. Chem. Soc. 1976, 98, 7891-7898.
29. Meot-Ner, M.; Sieck, L. W. J. Phys. Chem. 1986, 90, 6687-6690.
30. Paul, G. J. C.; Kebarle, P. J. Phys. Chem. 1990, 94, 5184-5189.
31. 2O.
32. 5CCH, it is unlikely. The structurally similar complex of benzyl anion and methanol has been calculated to be weakly bound, ∼12 kcal/mol, and has not been observed experimentally. See ref 23 and the following: Gatev, G.; Zhong, M.; Brauman J. I. J. Phys. Org. Chem. 1997, 10, 531-536.
33. Larson, J. W., McMahon, T. B. J. Am. Chem. Soc. 1984, 106, 517-521.
34. East, A. L. L.; Radom, L. J. Chem. Phys. 1997, 106, 6655-6674.
35. Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley: New York, 1976.
36. Su, T.; Chesnavich, W. J. J. Chem. Phys. 1982, 76, 5183-5185.
37. Frisch, M. J.; et al. Gaussian 94, Revision C.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
38. Smith, B. J.; Radom, L. Chem. Phys. Lett. 1995, 245, 123-128.
39. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
40. Pimentel, G. C.; McClellan, A. L. The Hydrogen Bond; Freeman: San Francisco, 1960.
41. Ions and Ion Pairs in Organic Reactions; Szwarc, M., Ed.; Wiley-Interscience: New York, 1972.
42. Hibbert, F.; Emsley, J. In Advances in Physical Organic Chemistry; Bethell, D., Ed.; Academic Press: London, 1990; Vol. 26.
43. Guthrie, J. P. Chem. Biol. 1996, 3, 163-170.
44. Gerlt, J. A.; Kreevoy, M. M.; Cleland, W. W.; Frey, P. A. Chem. Biol. 1997, 4, 259-267.
45. Shan, S.-O.; Loh, S.; Herschlag, D. Science 1996, 272, 97-101.
46. Stahl, N.; Jencks, W. P. J. Am. Chem. Soc. 1985, 108, 4196-4205.
47. Perrin, C. L.; Nielson, J. B. J. Am. Chem. Soc. 1997, 119, 12734-12741.
48. Leopold, K. R.; Fraser, G. T.; Novick, S. E.; Klemperer, W. Chem. Rev. 1994, 94, 1807-1827.
49. Hirota, E. Chem. Rev. 1992, 92, 141-173.
50. - and halide-water complexes have been examined. See: Kawaguchi, K.; Hirota, E. J. Chem. Phys. 1985, 84, 2953-2960. Ayotte, P.; Bailey, C. G.; Johnson, M. A. J. Phys. Chem. A 1998, 102, 3067-3071.
51. - and halide-water complexes have been examined. See: Kawaguchi, K.; Hirota, E. J. Chem. Phys. 1985, 84, 2953-2960. Ayotte, P.; Bailey, C. G.; Johnson, M. A. J. Phys. Chem. A 1998, 102, 3067-3071.
52. Larson, J. W.; McMahon, T. B. J. Am. Chem. Soc. 1987, 109, 6230-6236.
53. Dessent, C. E. H.; Kim, J.; Johnson, M. A. Acc. Chem. Res. 1998, 31, 527-534.
54. Bradforth, S. E.; Arnold, D. W.; Metz, R. B.; Weaver, A.; Neumark, D. M. J. Phys. Chem. 1991, 95, 8066-8078.
55. Meot-Ner, M.; Sieck, L. W. J. Am. Chem. Soc. 1986, 108, 7525-7529.
56. Davidson, W. R.; Sunner, J.; Kebarle, P. J. Am. Chem. Soc. 1979, 101, 1675-1680.
57. Zeegers-Huyskens, T. J. Mol. Struct. 1988, 177, 125-141.
58. Wolfe, S.; Hoz, S.; Kim, C.-K.; Yang, K. J. Am. Chem. Soc. 1990, 112, 4186-4191.
59. DeLaat, A. M.; Ault, B. S. J. Phys. Chem. 1987, 91, 4232-4236.
60. Fraser, G. T.; Leopold, K. R.; Klemperer, W. J. Chem. Phys. 1984, 80, 1423-1426.
61. Jeng, M.-L. H.; DeLaat, A. M.; Ault, B. S. J. Phys. Chem. 1989, 93, 3997-4000.
62. Cybulski, S. M.; Scheiner, S. J. Am. Chem. Soc. 1987, 109, 4199-4206.
63. Our estimate is based on the detection limit of our instrument and the pressure range available.
64. Chesnavich, W. J. J. Chem. Phys. 1986, 84, 2615-2619.
65. Lim, K. F.; Brauman, J. I. J. Chem. Phys. 1991, 94, 7164-7179.
66. Baer, S.; Moylan, C. R.; Brauman, J. I. J. Am. Chem. Soc. 1991, 113, 5942-5949.
67. The small negative frequency in both structures corresponded to a torsional motion of the methoxide anion. Attempts to eliminate the negative eigenvalue in both cases were not fruitful. Many similar conformations within a small energy range (<0.2 kcal/mol) were found, indicating that both structures were "loosely" bound.
68. Chabinyc, M. L.; Brauman, J. I. J. Am. Chem. Soc. 1998, 120, 10865-10870.
69. de Beer, E.; Kim, E. H.; Neumark, D. M.; Gunion, R. F.; Lineberger, W. C. J. Chem. Phys. 1995, 99, 13627-13636.
70. Blades, A.; Klassen, J. S.; Kebarle, P. J. Am. Chem. Soc. 1995, 117, 10563-10571.
71. Cumming, J. B.; French, M. A.; Kebarle, P. J. Am. Chem. Soc. 1977, 99, 6999-7003.
72. Morokuma, K. Acc. Chem. Res. 1977, 10, 294-300.
73. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 800-926.
74. Wladkowski, B. D.; East, A. L. L.; Mihalick, J. E.; Allen, W. D.; Brauman, J. I. J. Chem. Phys. 1993, 100, 2058-2088.
75. Platts, J.; Ladig, K. E. J. Phys. Chem. 1996, 100, 13455-13461.
76. Liebman, J. F.; Romm, M. J.; Meot-Ner, M.; Cyhulski, S. M.; Scheiner, S. J. Phys. Chem. 1991, 95, 1112-1119.
77. Gao, J.; Garner, D. S.; Jorgensen, W. L. J. Am. Chem. Soc. 1986, 108, 4784-4790.
78. Chen, J.; McAllister, M. A.; Lee, J. K.; Houk, K. N. J. Org. Chem. 1998, 63, 4611-4619.
79. Meot-Ner and co-workers have obtained results that appear to show that simple electrostatic arguments are adequate for some cationic systems. For example, see ref 4. These types of models have not been shown to have the same level of success for anionic systems. See refs 76 and 77.
80. Wiberg, K. B. J. Am. Chem. Soc. 1990, 112, 3379-3385.
81. Chauvel, J. P., Jr.; True, N. S. Chem. Phys. 1985, 95, 435-441.
82. Clearly, charge distributions are perturbed in the ion-molecule complex, and charge-transfer effects may be important. See: Weinhold, F. J. Mol. Struct. (THEOCHEM) 1997, 398-399, 181-197. Recent experimental work has suggested that neutral hydrogen bonds may have partial covalent character. (See: Cornilescu, G.; Hu, J.-S.; Bax, A. J. J. Am. Chem. Soc. 1999, 121, 2949. Isaacs, E. D.; Shukla, A.; Platzman, P. M.; Hamann, D. R.; Barbiellini, B.; Tulk, C. A. Phys. Rev. Lett. 1999, 82, 600-603). However, electrostatics provide a good qualitative model for understanding the interaction.
83. Clearly, charge distributions are perturbed in the ion-molecule complex, and charge-transfer effects may be important. See: Weinhold, F. J. Mol. Struct. (THEOCHEM) 1997, 398-399, 181-197. Recent experimental work has suggested that neutral hydrogen bonds may have partial covalent character. (See: Cornilescu, G.; Hu, J.-S.; Bax, A. J. J. Am. Chem. Soc. 1999, 121, 2949. Isaacs, E. D.; Shukla, A.; Platzman, P. M.; Hamann, D. R.; Barbiellini, B.; Tulk, C. A. Phys. Rev. Lett. 1999, 82, 600-603). However, electrostatics provide a good qualitative model for understanding the interaction.
84. Clearly, charge distributions are perturbed in the ion-molecule complex, and charge-transfer effects may be important. See: Weinhold, F. J. Mol. Struct. (THEOCHEM) 1997, 398-399, 181-197. Recent experimental work has suggested that neutral hydrogen bonds may have partial covalent character. (See: Cornilescu, G.; Hu, J.-S.; Bax, A. J. J. Am. Chem. Soc. 1999, 121, 2949. Isaacs, E. D.; Shukla, A.; Platzman, P. M.; Hamann, D. R.; Barbiellini, B.; Tulk, C. A. Phys. Rev. Lett. 1999, 82, 600-603). However, electrostatics provide a good qualitative model for understanding the interaction.
85. Hudson, R. F.; Eisenstein, O.; Anh, N. T. Tetrahedron 1975, 31, 751-756.
86. Janousek, B. K.; Zimmerman, A. H.; Reed, K. J.; Brauman, J. I. J. Am. Chem. Soc. 1978, 100, 6142-6148.
87. Wiberg, K. B.; Wendoloski, J. J. J. Phys. Chem. 1984, 88, 586-593.
88. Wiberg, K. B.; Rablen, P. R J. Am. Chem. Soc. 1993, 115, 9234-9242.
89. Schleyer, P. v. R. Pure Appl. Chem. 1987, 59, 1647-1660.
90. The interaction of the dipole of the substituent with the dipole of the hydrogen bond donor is small compared to their respective interactions with the charge. A simple estimation using Coulomb's law and ab initio point charges suggests that this interaction is only ∼5% of the total attractive electrostatic potential.
91. Grabowski, J. J.; DePuy, C. H.; Bierbaum, V. M. J. Am. Chem. Soc. 1983, 105, 2565-2571.
92. Squires, R. R.; Bierbaum, V. M.; Grabowski, J. J.; DePuy, C. H. J. Am. Chem. Soc. 1983, 105, 5185-5192.