Alkyl radicals as hydrogen bond acceptors: Computational evidence

Journal of the American Chemical Society

Volumn 131, Issue 24, 2009, Pages 8627-8635

  Hammerum, Steen ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION INTENSITY; ALKYL RADICALS; COMPUTATIONAL STUDIES; DONOR-ACCEPTOR; HYDROGEN BOND ACCEPTORS; HYDROGEN BOND STRENGTH; HYDROGEN BONDINGS; IONIZATION ENERGIES; PROTON AFFINITY; PROTON DONORS; STRETCHING FREQUENCY; STRUCTURAL INFORMATION;

ALKYLATION; BINDING SITES; BOND LENGTH; BOND STRENGTH (CHEMICAL); HYDROGEN; PROTON TRANSFER; PROTONS;

HYDROGEN BONDS;

ALKYL GROUP; FORMALDEHYDE; PROPANE; PROTON; RADICAL; WATER; ALKANE; FREE RADICAL;

ABSORPTION; ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; FOURIER TRANSFORMATION; HYDROGEN BOND; IONIZATION; MOLECULAR INTERACTION; SURFACE CHARGE; CHEMICAL MODEL; CHEMISTRY; INFRARED SPECTROPHOTOMETRY; STATIC ELECTRICITY; THERMODYNAMICS;

ALKANES; FREE RADICALS; HYDROGEN BONDING; MODELS, CHEMICAL; SPECTROPHOTOMETRY, INFRARED; STATIC ELECTRICITY; THERMODYNAMICS; WATER;

EID: 67650557275     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja901854t     Document Type: Article

References (164)

1. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
2. Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48.
3. Scheiner, S. Hydrogen Bonding, a Theoretical Perspective; Oxford University Press: New York, 1997.
4. Pauling, L. The Nature of the Chemical Bond; Cornell University Press: Ithaca, NY, 1939.
5. Gordon, M. S.; Jensen, J. H. Acc. Chem. Res. 1996, 29, 536.
6. (a) Alkorta, I.; Rozas, I.; Elguero, J. Chem. Soc. Rev. 1998, 27, 163.
7. (b) Rozas, I.; Alkorta, I.; Elguero, J. J. Am. Chem. Soc. 2000, 122, 11154.
8. (a) Jacox, M. E. Chem. Phys. 1979, 42, 133.
9. (b) Misochko, E. Y.; Benderskii, V. A.; Goldschleger, A. U.; Akimov, A. V.; Shestakov, A. F. J. Am. Chem. Soc. 1995, 117, 11997.
10. (c) Merritt, J. M.; Rudić, S.; Miller, R. E. J. Chem. Phys. 2006, 124, 084301.
11. Chen, Y.; Tschuikow-Roux, E.; Rauk, A. J. Phys. Chem. 1991, 95, 9832.
12. Alkorta, I.; Rozas, I.; Elguero, J. Ber. Bunsen-Ges. 1998, 102, 429.
13. (a) Tachikawa, H. J. Phys. Chem. A 1998, 102, 7065.
14. (b) Igarashi, M.; Ishibashi, T.; Tachikawa, H. J. Mol. Struct. 2002, 594, 61.
15. (c) Wang, B.-Q.; Li, Z.-R.; Wu, D.; Hao, X.-Y.; Li, R.-J.; Sun, C.-C. Chem. Phys. Lett. 2003, 375, 91.
16. (d) Tang, K.; Shi, F. Q. Int. J. Quantum Chem. 2007, 107, 665.
17. (e) Raghavendra, B.; Arunan, E. J. Phys. Chem. A 2007, 111, 9699.
18. (f) Li, Q.; An, X.; Luan, F.; Li, W.; Gong, B.; Cheng, J.; Sun, J. J. Chem. Phys. 2008, 128, 154102.
19. (g) An, X.; Liu, H.; Li, Q.; Gong, B.; Cheng, J. J. Phys. Chem. A 2008, 112, 5258.
20. (h) Crespo-Otero, R.; Sanchez-Garzia, E.; Suardiaz, R.; Montero, L. A.; Sander, W. Chem. Phys. 2008, 353, 193.
21. Li, Q.; An, X.; Gong, B.; Cheng, J. J. Mol. Struct. 2008, 866, 11.
22. Meot-Ner (Mautner), M. Chem. Rev. 2005, 105, 213.
23. (a) Gilli, G.; Gilli, P. J. Mol. Struct. 2000, 552, 1.
24. (b) Gilli, P.; Pretto, L.; Gilli, G. J. Mol. Struct. 2007, 844, 328.
25. (c) Gilli, P.; Pretto, L.; Bertolasi, V.; Gilli, G. Acc. Chem. Res. 2009, 42, 33.
26. Hammerum, S.; Nielsen, C. B. J. Phys. Chem. A 2005, 109, 12046.
27. (a) Cao, J.; Sun, W.; Holmes, J. L. Int. J. Mass Spectrom. 2002, 217, 179.
28. (b) Wang, X.; Sun, W.; Holmes, J. L. J. Phys. Chem. A 2006, 110, 8409.
29. Gil, A.; Sodupe, M.; Bertran, J. Chem. Phys. Lett. 2004, 395, 27.
30. (a) Nedev, H.; van der Rest, G.; Mourgues, P.; Audier, H. E. Eur. J. Mass Spectrom. 2003, 9, 319.
31. (b) Nedev, H.; van der Rest, G.; Mourgues, P.; Audier, H. E. Int. J. Mass Spectrom. 2004, 231, 197.
32. Bouchoux, G.; Choret, N. Int. J. Mass Spectrom. 2000, 201, 161.
33. Semialjac, M.; Loos, J.; Schröder, D.; Schwarz, H. Int. J. Mass Spectrom. 2002, 214, 129.
34. (a) Mayer, P. M.; Keister, J. W.; Baer, T.; Evans, M.; Ng, C. Y.; Hsu, C.-W. J. Phys. Chem. A 1997, 101, 1270.
35. (b) Mayer, P. M. Int. J. Mass Spectrom. 2002, 218, 1.
36. (a) Kitaura, K.; Morokuma, K. Int. J. Quantum Chem. 1976, 10, 305.
37. (b) Umeyama, H.; Morokuma, K. J. Am. Chem. Soc. 1977, 99, 1316.
38. (c) Morokuma, K. Acc. Chem. Res. 1977, 10, 294.
39. Bader, R. A. W. Atoms in Molecules; Clarendon Press: Oxford, UK, 1990.
40. Koch, U.; Popelier, P. L. A. J. Phys. Chem. 1995, 99, 9747.
41. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
42. Weinhold, F.; Landis, C. R. Valency and Bonding; Cambridge University Press: Cambridge, UK, 2005.
43. (a) Aloisio, S.; Francisco, J. S. Acc. Chem. Res. 2000, 33, 825.
44. (b) Hansen, J. C.; Francisco, J. S. ChemPhysChem 2002, 3, 833.
45. Qi, X.-J.; Lin, L.; Fu, Y.; Guo, Q.-X. Struct. Chem. 2005, 16, 347.
46. Frisch, M. J.; et al., Gaussian 03, rev. C2; Gaussian Inc: Wallingford, CT, 2004.
47. (a) Del Bene, J. E.; Person, W. B.; Szczepaniak, K. J. Phys. Chem. 1995, 99, 10705.
48. (b) Pan, Y. P.; McAllister, M. A. J. Mol. Struct. 1998, 427, 221.
49. (c) Koné, M.; Illien, B.; Graton, J.; Laurence, C. J. Phys. Chem. A 2005, 109, 11907.
50. (a) Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1998, 109, 7764.
51. (b) Baboul, A. G.; Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. J. Chem. Phys. 1999, 110, 7650.
52. (c) Curtiss, L. A.; Redfern, P. C.; Rassolov, V.; Kedziora, G.; Pople, J. A. J. Chem. Phys. 2001, 114, 9287.
53. Nicolaides, A.; Rauk, A.; Glukhovtsev, M. N.; Radom, L. J. Phys. Chem. 1996, 100, 17460.
54. Del Bene, J. E.; Shavitt, I. In Molecular Interactions Scheiner, S., Ed.; Wiley: New York, 1997; pp 157-179.
55. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.
56. Chase, M. W., Jr. NIST-JANAF Thermochemical Tables, 4th ed.; Journal of Physical Chemical Reference Data; National Institute of Standards and Technology and the American Institute of Physics: Melville, NY, 1998; Monograph No. 9.
57. (a) Guerra, C. F.; Bickelhaupt, F. M. Angew. Chem., Int. Ed. 1999, 38, 2942.
58. (b) Guerra, C. F.; Bickelhaupt, F. M.; Snijders, J. G.; Baerends, E. J. Chem. - Eur. J. 1999, 5, 3581.
59. (c) Guerra, C. F.; Bickelhaupt, F. M. Angew. Chem., Int. Ed. 2002, 41, 2092.
60. Grabowski, S. J. Ann. Rep. Prog. Chem., Sect. C 2006, 102, 131.
61. (a) Xantheas, S. S. J. Chem. Phys. 1996, 104, 8821.
62. (b) Bowen, J. P.; Sorensen, J. B.; Kirschner, K. N. J. Chem. Educ. 2007, 84, 1225.
63. (a) Adesokan, A. A.; Gerber, R. B. J. Phys. Chem. A 2009, 113, 1905.
64. (b) Oh, H.-B.; Lin, C.; Hwang, H. Y.; Zhai, H.; Breuker, K.; Zabroushov, V.; Carpenter, B. K.; McLafferty, F. W. J. Am. Chem. Soc. 2005, 127, 4076.
65. (c) Buckingham, A. D.; Del Bene, J. E.; McDowell, S. A. C. Chem. Phys. Lett. 2008, 463, 1.
66. Kryachko, E. S.; Zeegers-Huyskens, T. J. Phys. Chem. A 2003, 107, 7546.
67. (a) Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
68. (b) Jensen, F. Introduction to Computational Chemistry, 2nd. ed.; Wiley: Chichester, UK, 2007.
69. (a) Masamura, M. Theor. Chem. Acc. 2001, 106, 301.
70. (b) Cramer, C. J. Essentials of Computational Chemistry; Wiley: Chicester, UK, 2002.
71. Schaftenaar, G.; Noordik, J. H. J. Comput.-Aided Mol. Design 2000, 14, 123.
72. Ortiz Alba, J. C.; Jané, C. B. Xaim; Universitat Rovira i Virgili, Tarragona, Spain; http://www.quimica.urv.es/XAIM.
73. Bennett, S. L.; Field, F. H. J. Am. Chem. Soc. 1972, 94, 5188.
74. -1 (attributed to McMahon, T. B.).
75. Castleman, A. W.; Peterson, K. I.; Upschulte, B. L.; Schilling, F. J. Int. J. Mass Spectrom. Ion Phys. 1983, 47, 203.
76. (a) Hilbert, G. E.; Wulf, O. R.; Hendricks, S. B.; Liddel, U. J. Am. Chem. Soc. 1936, 58, 548.
77. (b) Hendricks, S. B.; Wulf, O. R.; Hilbert, G. E.; Liddel, U. J. Am. Chem. Soc. 1936, 58, 1991.
78. (c) Badger, R. M.; Bauer, S. H. J. Chem. Phys. 1937, 5, 839.
79. (a) Allerhand, A.; Schleyer, P. v. R. J. Am. Chem. Soc. 1963, 85, 1715.
80. (b) Pimentel, C. G.; McClellan, A. L. The Hydrogen Bond; Freeman: San Francisco, 1960;
81. (c) Fuster, F.; Silvi, B. Theor. Chem. Acc. 2000, 104, 13.
82. Thompson, W. H.; Hynes, J. T. J. Am. Chem. Soc. 2000, 122, 6278.
83. (a) Ratajczak, H.; Orville-Thomas, W. J.; Rao, C. N. R. Chem. Phys. 1976, 17, 197.
84. (b) Rao, C. N. R.; Dwivedi, P. C.; Ratajczak, H.; Orville-Thomas, W. J. J. Chem. Soc., Faraday Trans. 2 1974, 955.
85. Iogansen, A. V. Spectrochim. Acta 1999, 55, 1585.
86. Swanton, D. J.; Bacskay, G. B.; Hush, N. S. Chem. Phys. 1983, 82, 303.
87. Joseph, J.; Jemmis, E. D. J. Am. Chem. Soc. 2007, 129, 4620.
88. (a) Badger, R. M. J. Chem. Phys. 1934, 2, 128.
89. (b) Badger, R. M. J. Chem. Phys. 1935, 3, 710.
90. (c) Lippincott, E. R.; Schroeder, R. J. Chem. Phys. 1955, 23, 1099.
91. (d) Schroeder, R.; Lippincott, E. R. J. Phys. Chem. 1957, 51, 921.
92. (a) Mó, Y.; Yáñez, M.; Elguero, J. J. Chem. Phys. 1992, 97, 6628.
93. (b) Espinosa, E.; Souhassou, M.; Lachekar, H.; Lecomte, C. Acta Crystallogr. 1999, B55, 563.
94. (c) Grabowski, S. J. Monatsh. Chem. 2002, 133, 1373.
95. Olesen, S. G.; Hammerum, S. Europ. J. Mass Spectrom. 2009, 15, 239.
96. Carpenter, J. E.; Weinhold, F. J. Mol. Struct. 1988, 169, 41.
97. Karpichev, B.; Reisler, H.; Krylov, A. I.; Diri, K. J. Phys. Chem. A 2008, 112, 9965.
98. Fridgen, T. D. J. Phys. Chem. A 2006, 110, 6122.
99. (b) Burt, M. B.; Fridgen, T. D. J. Phys. Chem. A 2007, 111, 10738.
100. Scheiner, S. Acc. Chem. Res. 1994, 27, 402.
101. (a) Bouma, W. J.; Radom, L. Chem 1979, 64, 216.
102. (b) Pross, A.; Radom, L. J. Am. Chem. Soc. 1981, 103, 6049.
103. Gardenier, G. H.; Roscioli, J. R.; Johnson, M. A. J. Phys. Chem. A 2008, 112, 12022.
104. (a) Cybulski, S. M.; Scheiner, S. J. Phys. Chem. 1989, 93, 6565.
105. (b) Solcà, N.; Dopfer, O. J. Phys. Chem. A 2005, 109, 6174.
106. (c) Qian, W.; Krimm, S. J. Phys. Chem. A 2005, 109, 5608.
107. (d) Stone, A. J. The Theory of Intramolecular Forces; Oxford University Press: Oxford, UK, 1996.
108. (a) Liebman, J. F.; Romm, M. J.; Meot-Ner (Mautner), M.; Cybulski, S. M.; Scheiner, S. J. Phys. Chem. 1991, 95, 1112.
109. (b) Meot-Ner (Mautner), M.; Sieck, L. W.; Liebman, J. F.; Scheiner, S. J. Phys. Chem. 1996, 100, 6445.
110. Goebbert, D. J.; Wenthold, P. G. Europ. J. Mass Spectrom. 2004, 10, 837.
111. Pendás, A. M.; Blanco, M. A.; Francisco, E. J. Chem. Phys. 2006, 125, 184112.
112. (a) Glendening, E. D.; Streitwieser, A. J. Chem. Phys. 1994, 100, 2900.
113. (b) Glendening, E. D. J. Phys. Chem. A 2005, 109, 11936.
114. Larson, J. W.; McMahon, T. B. J. Am. Chem. Soc. 1982, 104, 6255.
115. (a) Davidson, W. R.; Sunner, J.; Kebarle, P. J. Am. Chem. Soc. 1979, 101, 1675.
116. (b) Desmeules, P. J.; Allen, L. C. J. Chem. Phys. 1980, 72, 4731.
117. (a) Chen, J.; McAllister, M. A.; Lee, J. K.; Houk, K. N. J. Org. Chem. 1998, 63, 4611.
118. (b) Shan, S.; Loh, S.; Herschlag, D. Science 1996, 272, 97.
119. (a) Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1984, 106, 1257.
120. (b) Speller, C. V.; Meot-Ner (Mautner), M. J. Phys. Chem. 1985, 89, 5217.
121. (c) Meot-Ner (Mautner), M.; Sieck, L. W. J. Phys. Chem. 1985, 89, 5222.
122. Mayer, P. M. J. Phys. Chem. A 1999, 103, 5905.
123. Lankau, T.; Yu, C.-H. Phys. Chem. Chem. Phys. 2007, 9, 299.
124. Remer, L. C.; Jensen, J. H. J. Phys. Chem. A 2000, 104, 9266.
125. Özen, A. S.; De Proft, F.; Aviyente, V.; Geerlings, P. J. Phys. Chem. A 2006, 110, 5860.
126. (a) Caldwell, G.; Rozeboom, M. D.; Kiplinger, J. P.; Bartmess, J. E. J. Am. Chem. Soc. 1984, 106, 4660.
127. (b) Zeegers-Huyskens, T. J. Mol. Struct. 1986, 135, 93.
128. (c) Nguyen, M. T.; Leroux, N.; Zeegers-Huyskens, T. J. Mol. Struct. 1997, 404, 75.
129. (d) Zeegers-Huyskens, T. J. Org. Chem. 1999, 64, 4946.
130. (e) Chandra, A. K.; Zeegers-Huyskens, T. J. Org. Chem. 2003, 68, 3618.
131. (f) Chandra, A. K.; Nguyen, M. T.; Zeegers-Huyskens, T. J. Phys. Chem. A 1998, 102, 6010.
132. Bian, L. J. Phys. Chem. A 2003, 107, 11517.
133. Chan, B.; Del Bene, J. E.; Radom, L. J. Am. Chem. Soc. 2007, 129, 12197.
134. (a) Zeegers-Huyskens, T. Chem. Phys. Lett. 1986, 129, 172.
135. (b) Zeegers-Huyskens, T. J. Mol. Struct. 1988, 177, 125.
136. (a) Humbel, S. J. Phys. Chem. A 2002, 106, 5517.
137. (b) Humbel, S.; Hoffmann, N.; Côte, I.; Bouquart, J. Chem. - Eur. J. 2000, 6, 1592.
138. (a) Gordy, W.; Stanford, S. C. J. Chem. Phys. 1940, 8, 170.
139. (b) Hammett, L. P. J. Chem. Phys. 1940, 8, 644.
140. (c) Ault, B. S.; Steinback, E.; Pimentel, G. C. J. Phys. Chem. 1975, 79, 615.
141. (d) Barnes, A. J. J. Mol. Struct. 1983, 100, 259.
142. (e) Zeegers-Huyskens, T. J. Mol. Liq. 1995, 67, 33.
143. (f) Fridgen, T. D.; MacAleese, L.; Maitre, P.; McMahon, T. B.; Boissel, P.; Lemaire, J. Phys. Chem. Chem. Phys. 2005, 7, 2747.
144. (g) Roscioli, J. R.; McCunn, L. R.; Johnson, M. A. Science 2007, 316, 249.
145. Chan, B.; Del Bene, J. E.; Elguero, J.; Radom, L. J. Phys. Chem. A 2005, 109, 5509.
146. Tsubomura, H. Bull. Chem. Soc. Jpn. 1954, 27, 445.
147. (a) Coulson, C. A.; Danielsson, U. Ark. Fys. 1954, 8, 239.
148. (b) Coulson, C. A.; Danielsson, U. Ark. Fys. 1954, 8, 245.
149. (c) Coulson, C. A. Research, Sci. Appl. Ind. 1957, 10, 149.
150. (d) Coulson, C. A.; In Hydrogen Bonding; Hadzi, D., Ed.; Pergamon Press: London, 1959; pp 339-355.
151. Puranik, P. G.; Kumar, V. Proc. Ind. Acad. Sci. 1963, 58, 29.
152. Szczepaniak, K.; Tramer, A. J. Phys. Chem. 1967, 71, 3035.
153. (a) Ratajczak, H. J. Phys. Chem. 1972, 76, 3000.
154. (b) Ratajczak, H.; Orville-Thomas, W. J. J. Chem. Phys. 1973, 58, 911.
155. (c) Ratajczak, H.; Orville-Thomas, W. J. J. Mol. Struct. 1975, 26, 387.
156. Allen, L. C. J. Am. Chem. Soc. 1975, 97, 6921.
157. Alabugin, I. V.; Manoharan, M.; Peabody, S.; Weinhold, F. J. Am. Chem. Soc. 2003, 125, 5973.
158. (a) Maksić, Z. B.; Vianello, R. J. Phys. Chem. A 2002, 106, 419.
159. (b) Deakyne, C. Int. J. Mass Spectrom. 2003, 227, 601.
160. Rablen, P. R.; Lockman, J. W.; Jorgensen, W. L. J. Phys. Chem. A 1998, 102, 3782.
161. (a) Spiegel, D. A.; Wiberg, K. B.; Schacherer, L. N.; Medeiros, M. R.; Wood, J. L. J. Am. Chem. Soc. 2005, 127, 12513.
162. (b) Pozzi, D.; Scanlan, E. M.; Renaud, P. J. Am. Chem. Soc. 2005, 127, 14204.
163. (c) Cuerva, J. M.; Campaña, A. G.; Justicia, J.; Rosales, A.; Oller-López, J. L.; Robles, R.; Cárdenas, D. J.; Buñuel, E.; Oltra, J. E. Angew. Chem., Int. Ed. 2006, 45, 5522.
164. (d) Tantawy, W.; Zipse, H. Eur. J. Org. Chem. 2007, 5817.