Hydride affinity scale of various substituted arylcarbeniums in acetonitrile

Journal of Physical Chemistry A

Volumn 114, Issue 50, 2010, Pages 13244-13256

  Zhu, Xiao Qing ^a   Wang, Chun Hua ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE RING; C-H BOND; ELECTRON WITHDRAWING GROUP; ELECTRON-DONATING; ELECTRON-DONATING GROUP; ELECTROPHILICITY; GASPHASE; GIBBS FREE ENERGY CHANGES; HOMOLYTIC DISSOCIATION; HYDRIDE TRANSFERS; INTEGRAL EQUATION FORMALISMS; LINEAR RELATIONSHIPS; PHENYL RINGS; POLARIZED CONTINUUM MODELS; REDUCTION POTENTIAL;

ACETONITRILE; BENZENE; CONTINUUM MECHANICS; INTEGRAL EQUATIONS;

HYDRIDES;

ACETONITRILE; ACETONITRILE DERIVATIVE; CARBON; HYDROGEN;

ARTICLE; CHEMISTRY; ELECTRON; QUANTUM THEORY; REPRODUCIBILITY; THERMODYNAMICS;

ACETONITRILES; CARBON; ELECTRONS; HYDROGEN; QUANTUM THEORY; REPRODUCIBILITY OF RESULTS; THERMODYNAMICS;

EID: 79953275912     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp109149x     Document Type: Article

References (134)

1. Examples in organometallics: (a) Sanders, A.; Cohen, L.; Geiring, W. P.; Kenedy, D.; Magatti, C. V. J. Am. Chem. Soc. 1973, 95, 5430.
2. Kiel, W. A.; Lin, G.-Y.; Gladysz, J. A. J. Am. Chem. Soc. 1980, 102, 3299.
3. Hayes, J. C.; Pearson, G. D. N.; Cooper, N. J. J. Am. Chem. Soc. 1981, 103, 4648.
4. Hayes, J. C.; Cooper, N. J. J. Am. Chem. Soc. 1982, 104, 5570.
5. Hayes, J. C.; Jernakoff, P.; Miller, G. A.; Cooper, N. J. Pure Appl. Chem. 1984, 56, 25.
6. Asaro, M. F.; Bodner, G. S.; Gladysz, J. A.; Cooper, S. R.; Cooper, N. J. Organometallics 1985, 4, 1020.
7. Guerchais, V.; Lapinte, C. J. Chem. Soc., Chem. Commun. 1986, 663.
8. Green, M. L. H.; Nagy, P. L. I. J. Organomet. Chem. 1963, 1, 58.
9. Slack, D. A.; Baird, M. C. J. Chem. Soc., Chem. Commun. 1974, 701.
10. Laycock, D. E.; Hartgarink, J.; Baird, M. C. J. Org. Chem. 1980, 45, 291.
11. Bly, R. S.; Silverman, G. S.; Hossain, M. M.; Bly, R. K. Organometallics 1984, 3, 642.
12. Hneihen, A. S.; Fermin, M. C.; Maas, J. J.; Bruno, J. W. J. Organomet. Chem. 1992, 429, C33-C37.
13. Recent examples in organometallics: (a) Sarker, N.; Bruno, J. W. Organometallics 2001, 20, 55.
14. Cheng, T.-Y.; Bullock, R. M. Organometallics 2002, 21, 2325.
15. Sarker, N.; Bruno, J. W. J. Am. Chem. Soc. 1999, 121, 2174.
16. Cheng, T.-Y.; Bullock, R. M. J. Am. Chem. Soc. 1999, 121, 3150.
17. Ellis, W. W.; Miedaner, A.; Curtis, C. J.; Gibson, D. H.; DuBois, D. L. J. Am. Chem. Soc. 2002, 124, 1926.
18. Ellis, W. W.; Ciancanelli, R.; Miller, S. M.; Raebiger, J. W.; DuBois, M. R.; DuBios, D. L. J. Am. Chem. Soc. 2003, 125, 12230.
19. Ellis, W. W.; Raebiger, J. W.; Curtis, C. J.; Bruno, J. W.; DuBios, D. L. J. Am. Chem. Soc. 2004, 126, 2738.
20. Recent examples in physical organic chemistry: (a) Cope, A. C.; Martin, M. M.; McKervey, M. A. Q. Rev., Chem. Soc. 1966, 20, 119.
21. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 4th ed.; Springer Sciences & Business Inc.: New York, 2000; Part A, pp 316-323.
22. Zhu, X.-Q.; Yang, Y.; Zhang, M.; Cheng, J.-P. J. Am. Chem. Soc. 2003, 125, 15298.
23. Zhu, X.-Q.; Cao, L.; Liu, Y.; Yang, Y.; Lu, J. Y.; Cheng, J.-P. Chem.-Eur. J. 2003, 9, 3937.
24. Zhu, X.-Q.; Li, zprint>, ]?>; LiMzfn > Q., H. R.; Ai, T.; Lu, J. Y.; Yang, Y.; Cheng, J.-P. Chem.-Eur. J. 2003, 9, 871.
25. Lee, I.-S.; Chow, K.-H.; Kreevoy, M. M. J. Am. Chem. Soc. 2002, 124, 7755, and references therein.
26. Arnett, E. M.; Flowers, R. A.; Meekhof, A. E.; Miller, L. J. Am. Chem. Soc. 1993, 115, 12603.
27. Arnett, E. M.; Flowers, R. A.; Ludwig, R. T.; Meekhof, A. E.; Walek, S. A. J. Phys. Org. Chem. 1997, 10, 499.
28. Olah, G. A.; Molnar, A. Hydrocarbon Chemistry; Wiley-Interscience: New York, 1995.
29. Olah, G. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1393-1405.
30. Vogel, P. Carbocarbenium Chemistry; Elsevier: Amsterdam, 1985.
31. Isaacs, N. Physical Organic Chemistry, 2nd ed.; Longman Scientific: London, 1995; Chapter 10.
32. Zhang, X. M.; Bruno, J. W.; Enyinnaya, E. J. Org. Chem. 1998, 63, 4671, and reference therein.
33. Cheng, J.-P.; Handoo, K. L.; Parker, V. D. J. Am. Chem. Soc. 1993, 115, 2655.
34. Deno, N. C.; Jaruzelski, J. J.; Schiriesheim, A. J. Am. Chem. Soc. 1955, 77, 3044-3051.
35. Arnett, E. M.; Bushick, R. D. J. Am. Chem. Soc. 1964, 86, 1564.
36. Bethell, D.; Gold, V. Carbonium Ions; Academic Press: New York, 1967.
37. Rochester, C. H. Acidity Functions; Academic Press: New York, 1970.
38. Liler, M. Reaction Mechanisms in Sulfuic Acid; Academic Press: New York, 1971.
39. Arnett, E. M.; Petro, S. C. J. Am. Chem. Soc. 1978, 100, 2563, 5402, 5408.
40. Arnett, E. M.; Petro, S. C.; Schleyer, P. v. R. J. Am. Chem. Soc. 1979, 101, 522.
41. Arnett, E. M.; Pienta, N. J. J. Am. Chem. Soc. 1980, 102, 3329.
42. Arnett, E. M.; Hofelich, T. C. J. Am. Chem. Soc. 1983, 105, 2889.
43. Arnett, E. M.; Hofelich, T. C. J. Am. Chem. Soc. 1982, 104, 3522.
44. Cheng, J.-P.; Handoo, K. L.; Xue, J.; Parker, V. D. J. Org. Chem. 1993, 58, 5050.
45. Handoo, K. L.; Cheng, J.-P.; Parker, V. D. J. Am. Chem. Soc. 1993, 115, 5067.
46. Parker, V. D. Acta Chem. Scand. 1992, 46, 1133.
47. Hunter, E. P.; Lias, S. G. In NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Mallard, W. G., Ed.; National Institute of Standards and Technology: Gaithersburg, MD, 2003. http://webbook.nist.gov.
48. Vianello, R.; Peran, N.; Maksic, Z. B. J. Phys. Chem. A 2006, 110, 12870.
49. Bean, G. P. J. Org. Chem. 1993, 58, 7336.
50. Robbins, A. M.; Jin, P.; Brinck, T.; Murray, J. S.; Politzer, P. Int. J. Quantum Chem. 2006, 106, 2904.
51. Grunenberg, J.; Laschat, S.; Dickner, T. Eur. J. Org. Chem. 2003, 4897.
52. Wayner, D. D. D.; Sim, B. A. J. Org. Chem. 1991, 56, 4853.
53. Reynolds, C. H. J. Am. Chem. Soc. 1992, 114, 8676.
54. Teberekidis, V. I.; Sigalas, M P. Tetrahedron 2005, 61, 3967.
55. Robbins, A. M.; Jin, P.; Brinck, T.; Murray, J. S.; Politzer, P. Int. J. Quantum Chem. 2006, 106, 2904.
56. Wurthwein, E. U.; Lang, G.; Shappele, L. H.; Mayr, H. J. Am. Chem. Soc. 2002, 124, 4084.
57. Mandado, M.; Van Alsenoy, C.; Mosquera, R. A. Chem. Phys. Lett. 2005, 405, 10 and references therein;
58. J. Phys. Chem. A 2004, 108, 7050.
59. Jorgensen, W. L.; Briggs, J. M.; Gao, J. J. Am. Chem. Soc. 1987, 109, 6857.
60. Rullmann, J. A. C.; van Duijnen, P. Th. Mol. Phys. 1988, 63, 451.
61. Guissani, Y.; Guillot, B.; Bratos, S. J. Chem. Phys. 1988, 88, 5850.
62. Gao, J.; Li, N.; Freinforf, M. J. Am. Chem. Soc. 1996, 118, 4912.
63. Figueirido, F.; Del Buono, G. S.; Levy, R. M. J. Phys. Chem. 1996, 100, 6389.
64. Byun, K.; Mo, Y.; Gao, J. J. Am. Chem. Soc. 2001, 123, 3974.
65. Florian, J.; Warshel, A. J. Phys. Chem. B 1997, 101, 5583.
66. (a) Lim, C.; Bashford, D.; Karplus, M. J. Phys. Chem. 1991, 95, 5610.
67. Kawata, M.; Ten-no, S.; Kato, S.; Hirata, F. Chem. Phys. 1996, 203, 53.
68. Kawata, M.; Ten-no, S.; Kato, S.; Hirata, F. J. Phys. Chem. 1996, 100, 1111.
69. Sato, H.; Hirata, F. J. Phys. Chem. A 1998, 102, 2603.
70. Sato, H.; Hirata, F. J. Phys. Chem. B 1999, 103, 6596.
71. (a) Topol, I. A.; Tawa, G. J.; Caldwell, R. A.; Eissenstat, M. A.; Burt, S. K. J. Phys. Chem. A 2000, 104, 9619.
72. Jang, Y. H.; Sowers, L. C.; Cagin, T.; Goddard, W. A., III. J. Phys. Chem. A 2001, 105, 274.
73. Klicic, J. J.; Friesner, R. A.; Liu, S.-Y.; Guida, W. C. J. Phys. Chem. A 2002, 106, 1327.
74. Adam, K. R. J. Phys. Chem. A 2002, 106, 11963.
75. (a) Cramer, C. J.; Truhlar, D. G. Rev. Comput. Chem. 1995, 6, 1.
76. Cramer, C. J.; Truhlar, D. G. Chem. Rev. 1999, 99, 2161.
77. Hou, T.; Xu, X. Prog. Chem. 2004, 16, 153.
78. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999.
79. (a) Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210.
80. Cammi, R.; Mennucci, B.; Tomasi, J. J. Phys. Chem. A 1998, 102, 870.
81. Cammi, R.; Mennucci, B.; Tomasi, J. J. Phys. Chem. A 2000, 104, 4690.
82. Fu, Y.; Liu, L.; Li, R. Q.; Liu, R.; Guo, Q. X. J. Am. Chem. Soc. 2004, 126, 814.
83. Fu, Y.; Liu, L.; Yu, H.-Z.; Wang, Y.-M.; Guo, Q.-X. J. Am. Chem. Soc. 2005, 127, 7227.
84. (a) Zhu, X.-Q.; Wang, C.-H.; Liang, H.; Cheng, J.-P. J. Org. Chem. 2006, 72, 945.
85. Zhu, X.-Q.; Wang, C.-H. J. Org. Chem., in press.
86. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T., Jr.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L. Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.01; Gaussian, Inc.: Wallingford, CT, 2004.
87. (a) Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43.
88. Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 106, 5151.
89. (a) Zhang, H. Y.; Sun, Y. M.; Wang, X. L. J. Org. Chem. 2002, 67, 2709.
90. Chandra, A. K.; Nam, P. C.; Nguyen, M. T. J. Phys. Chem. A 2003, 107, 9182.
91. Feng, Y.; Wang, J. T.; Guo, Q. X. J. Phys. Org. Chem. 2003, 16, 883.
92. Johnson, J. R. T.; Panas, I. Inorg. Chem. 2000, 39, 3181.
93. Johnson, J. R. T.; Panas, I. Inorg. Chem. 2000, 39, 3192.
94. Johnson, J. R. T.; Panas, I. Chem. Phys. Lett. 2001, 348, 433.
95. Johnson, J. R. T.; Panas, I. Phys. Chem. Chem. Phys. 2001, 3, 5482.
96. Johnson, J. R. T.; Panas, I. Chem. Phys. 2002, 276, 45.
97. Johnson, J. R. T.; Panas, I. J. Phys. Chem. A 2002, 106, 184.
98. (a) da Silva, C. O.; da Silva, E. C.; Nascimento, M. A. C. J. Phys. Chem. A 1999, 103, 11194.
99. da Silva, C. O.; da Silva, E. C.; Nascimento, M. A. C. J. Phys. Chem. A 2000, 104, 2402.
100. Liptak, M. D.; Shields, G. C. J. Am. Chem. Soc. 2001, 123, 7314.
101. Toth, A. M.; Liptak, M. D.; Phillips, D. L.; Schields, G. C. J. Chem. Phys. 2001, 114, 4595.
102. Liptak, M.; Shields, G. C. Int. J. Quantum Chem. 2001, 85, 727.
103. Liptak, M. D.; Gross, K. C.; Seybold, P. G.; Feldgus, S.; Shields, G. C. J. Am. Chem. Soc. 2002, 124, 6421.
104. Namazian, M.; Heidary, H. THEOCHEM 2003, 620, 257.
105. Saracino, G. A. A.; Improta, R.; Barone, V. Chem. Phys. Lett. 2003, 373, 411.
106. Namazian, M.; Almodarresieh, H. A. J. Mol. Struct. 2004, 686, 97.
107. Heravi, M. J.; Namazian, M.; Peacock, T. E. J. Electroanal. Chem. 1995, 385, 1.
108. Heravi, M. J.; Namazian, M. J. Electroanal. Chem. 1997, 425, 139.
109. (a) Fu, Y.; Shen, K.; Liu, L.; Guo, Q. X. J. Am. Chem. Soc. 2007, 129, 13510.
110. Qi, X. J.; Liu, L.; Fu, Y.; Guo, Q.-X. Organometallics 2006, 25, 5879.
111. Fu, Y.; Liu, L.; Yu, H. Z.; Wang, Y. M.; Guo, Q.-X. J. Am. Chem. Soc. 2005, 127, 7227.
112. Fu, Y.; Liu, L.; Li, R. Q.; Liu, R.; Guo, Q.-X. J. Am. Chem. Soc. 2004, 126, 814.
113. Fu, Y.; Wang, H. J.; Chong, S. S.; Guo, Q.-X.; Liu, L. J. Org. Chem. 2009, 74, 810.
114. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43.
115. Kim, C. K.; Han, I. S.; Ryu, W. S.; Lee, H. W.; Lee, B. S.; Kim, C. K. J. Phys. Chem. A 2006, 110, 2500.
116. (a) Freedman, H. H. In Carbonium Ions; Olah, G. A., Schleyer, P. v. R., Wiley: New York, 1973; Vol. IV, Chapter 28.
117. Okamoto, K.; Takeuchi, K.; Kitagawa, T. Adv. Phys. Org. Chem. 1995, 30, 173.
118. Turnbo, R. G.; Sullivan, D. L.; Pettit, R. J. Am. Chem. Soc. 1964, 86, 5630, and reference therein.
119. Horn, M.; Mayr, H. Chem.-Eur. J. 2010, 16, 7478.
120. Denekamp, C.; Sandlers, Y. Angew. Chem., Int. Ed. 2006, 45, 2093.
121. Mayr, H.; Patz, M. Angew. Chem. 1994, 106, 938;
122. Angew. Chem., Int. Ed. Engl. 1994, 33, 990.
123. Roth, M.; Mayr, H. Angew. Chem. 1995, 107, 2428;
124. Angew. Chem., Int. Ed. Engl. 1994, 34, 2250.
125. Mayr, H.; Bug, T.; Gotta, M. F.; Hering, N.; Irrgang, B.; Janker, B.; Kempt, B.; Loos, R.; Ofial, A.; Remennikov, G.; Schimmel, H. J. Am. Chem. Soc. 2001, 123, 9500.
126. Minegishi, S.; Mayr, H. J. Am. Chem. Soc. 2003, 125, 286.
127. Lucius, R.; Loos, R.; Mayr, H. Angew. Chem. 2002, 114, 97;
128. Angew. Chem., Int. Ed. 2002, 41, 92.
129. Mayr, H. Angew. Chem. 1990, 102, 1415;
130. Angew. Chem., Int. Ed. Engl. 1990, 29, 1371.
131. Schimdele, C.; Houk, K. N.; Mayr, H. J. Am. Chem. Soc. 2002, 124, 11208.
132. Denekamp, C.; Sandlers, Y. Angew. Chem., Int. Ed. 2006, 118, 2147.
133. Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press: Boca Raton, FL, 2003.
134. Pratt, D. A.; Dilabio, G. A.; Mulder, P.; Ingold, K. U. Acc. Chem. Res. 2004, 37, 334.