Effects of geminal disubstitution on C-H and N-H bond dissociation energies

Tetrahedron

Volumn 60, Issue 44, 2004, Pages 9909-9923

  Song, Ke Sheng ^a   Liu, Lei ^a   Guo, Qing Xiang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Anomeric effect; Bond dissociation energy; Captodative effect; Composite ab initio; Geminal effect

Indexed keywords

AMINE; AMMONIA; CARBON; METHANE; METHYL GROUP; NITROGEN;

AB INITIO CALCULATION; ARTICLE; CONFORMATION; CONJUGATION; DISSOCIATION; ELECTRICITY; ENERGY; HYDROGEN BOND; PRIORITY JOURNAL; SEPARATION TECHNIQUE; SUBSTITUTION REACTION;

EID: 4644269811     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.08.028     Document Type: Article

References (88)

1. K.U. Ingold, and J.S. Wright J. Chem. Educ. 77 2000 1062
2. C.Z. Cao, and Y.B. Lin Chin. J. Org. Chem. 23 2003 207
3. D.F. McMillen, and D.M. Golden Annu. Rev. Phys. Chem. 33 1982 493
4. S.J. Blanksby, and G.B. Ellison Acc. Chem. Res. 36 2003 255
5. H.G. Viehe, Z. Janousek, and R. Merenyi Substituent Effects in Radical Chemistry 1986 Reidel Dordrecht, The Netherland
6. X.-K. Jiang Acc. Chem. Res. 30 1997 283
7. A.R. Cherkasov, M. Jonsson, V.I. Galkin, and R.A. Cherkasov Russ. Chem. Rev. 70 2001 1
8. J. Berkowitz, G.B. Ellison, and D. Gutman J. Phys. Chem. 98 1994 2744
9. L.-S. Sheng, L. Tao, F. Qi, Y.-W. Zhang, and S.-Q. Yu Acta Chim. Sinica 53 1995 209
10. F.H. Bordwell, and X.-M. Zhang Acc. Chem. Res. 26 1993 510
11. L.J.J. Laarhoven, P. Mulder, and D.D.M. Wayner Acc. Chem. Res. 32 1999 342
12. Q. Zeng, J.-Q. He, and J.-P. Cheng Chem. J. Chin. Univ. 23 2002 1285
13. K.-S. Song, L. Liu, and Q.-X. Guo J. Org. Chem. 68 2003 4604
14. J.P. Cheng, B. Liu, Y. Lu, J.L. Mi, and Z.W. Huan Chem. J. Chin. Univ. 18 1997 1080
15. B. Liu, Z.W. Huan, and J.P. Cheng Acta Chim. Sinica 55 1997 123
16. D.J. Henry, C.J. Parkinson, P.M. Mayer, and L. Radom J. Phys. Chem. A 105 2001 6750
17. K.-S. Song, Y.-H. Cheng, Y. Fu, L. Liu, X.-S. Li, and Q.-X. Guo J. Phys. Chem. A 106 2002 6651
18. P.M. Mayer, C.J. Parkinson, D.M. Smith, and L. Radom J. Chem. Phys. 108 1998 604
19. C.J. Parkinson, P.M. Mayer, and L. Radom Theor. Chem. Acc. 102 1999 92
20. C.J. Parkinson, P.M. Mayer, and L. Radom J. Chem. Soc., Perkin Trans. 2 1999 2305
21. Y. Feng, L. Liu, J.-T. Wang, H. Huang, and Q.-X. Guo J. Chem. Inf. Comput. Sci. 43 2003 2005
22. Y. Fu, L. Liu, B.-L. Lin, Y. Mou, Y.-H. Cheng, and Q.-X. Guo J. Org. Chem. 68 2003 4657
23. D. Crans, T. Clark, and P.v.R. Schleyer Tetrahedron Lett. 21 1980 3681
24. K.B. Clark, D.D.M. Wayner, S.H. Demirdji, and T.H. Koch J. Am. Chem. Soc. 115 1993 2447
25. D.J. Pasto J. Am. Chem. Soc. 110 1988 8164
26. D.J. Pasto J. Phys. Org. Chem. 10 1997 475
27. G. Leroy, M. Sana, and C. Wilante J. Mol. Struct. (Theochem) 80 1991 303
28. M. Karelson, A.R. Katritzky, and M.C. Zerner J. Org. Chem. 56 1991 134
29. W.X. Li, X.J. Zhou, G.Q. Cai, and Q.S. Yu Chin. Sci. Bull. 37 1992 302
30. W. Li, X. Zhou, and G. Cai Acta Phys.-Chim. Sinica 9 1993 402
31. W. Li, X. Zhou, N. Wu, and G. Cai Chin. Chem. Lett. 4 1993 73
32. Q. Yu, G. Cai, N. Wu, and W. Li Acta Phys.-Chim. Sinica 10 1994 765
33. N. Wu, G. Cai, and Q. Yu Chin. J. Chem. Phys. 7 1994 380
34. H.G. Viehe, Z. Janousek, R. Merenyi, and L. Stella Acc. Chem. Res. 18 1985 148
35. R. Sustmann, and H.G. Korth Adv. Phys. Org. Chem. 26 1990 131
36. K. Pius, M. Jain, and J. Chandrasekhar J. Mol. Struct. (Theochem) 361 1996 191
37. J. Cioslowski, and T. Varnali J. Phys. Chem. 100 1996 18725
38. E.R. Davidson, S. Chakravorty, and J.J. Gajewski New. J. Chem. 21 1997 533
39. J.J. Brocks, F.M. Welle, H.-D. Beckhaus, and C. Richardt Tetrahedron Lett. 38 1997 7721
40. M. Lucarini, G. Pedrielli, F. Pedulli, L. Valgimigli, D. Gigmes, and P. Tordo J. Am. Chem. Soc. 121 1999 11546
41. D.A. Pratt, G.A. DiLabio, L. Valgimigli, G.F. Pedulli, and K.U. Ingold J. Am. Chem. Soc. 124 2002 11085
42. Z. Li, and J.-P. Cheng J. Org. Chem. 68 2003 7350
43. D. Kost, M. Raban, and K. Aviram J. Chem. Soc., Chem. Commun. 1986 346
44. J.P. Cheng, B. Liu, Z. Li, and Z.W. Huan Chin. Sci. Bull. 40 1995 1338
45. J.P. Cheng, D.F. Wang, J.L. Mi, and Z. Yin Chin. Sin. Bull. 42 1997 1538
46. J.P. Cheng, Y. Lu, B. Liu, Y.Y. Zhao, D.F. Wang, Y.K. Sun, and J.L. Mi Sci. China Ser. B: Chem. 41 1998 215
47. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; 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 A.1, Gaussian, Inc., Pittsburgh PA, 2003.
48. A.P. Scott, and L.J. Radom Phys. Chem. 100 1996 16502
49. L.A. Curtiss, K. Raghavachari, P.C. Redfern, V. Rassolov, and J.A. Pople J. Chem. Phys. 109 1998 7764
50. L.A. Curtiss, K.P.C. Redfern, and J.A. Pople J. Chem. Phys. 112 2000 7374
51. B.J. Lynch, and D.G. Truhlar J. Phys. Chem. A 107 2003 3898
52. Z.F. Hu, X. Feng, Z.Y. Wang, and S.K. Zhou Acta Chim. Sinica 60 2002 1760
53. J.W. Ochterski, G.A. Petersson, and K.B. Wiberg J. Am. Chem. Soc. 117 1995 11299
54. J.W. Ochterski, G.A. Petersson, and J.A. Montgomery Jr. J. Chem. Phys. 104 1996 2598
55. A.G. Baboul, L.A. Curtiss, P.C. Redfern, and K. Raghavachari J. Chem. Phys. 110 1999 7650
56. M. Li, W. Shen, and D.-Y. Tang Acta Chim. Sinica 61 2003 1251
57. Y.-R. Luo Handbook of Bond Dissociation Energies in Organic Compounds 2003 CRC Floride (b) For the compounds that have more than one experimental BDEs, the recommended data in the handbook were used.
58. X-Q. Yao, X.-J. Hou, H. Jiao, H.-W. Xiang, and Y.-W. Li J. Phys. Chem. A 107 2003 9991
59. E.R. Johnson, O.J. Clarkin, and G.A. DiLabio J. Phys. Chem. A 107 2003 9953
60. L.F. Wang, and H.Y. Zhang Chin. J. Chem. 21 2003 1669
61. B.L. Lin, Y. Fu, L. Liu, and Q.X. Guo Chin. Chem. Lett. 14 2003 1073
62. H.-Y. Zhang, Y.-M. Sun, and X.-L. Wang Chem. Eur. J. 9 2003 502
63. H.Y. Zhang, Y.M. Sun, and D.Z. Chen Chin. Chem. Lett. 13 2002 531
64. X.-Q. Yao, X.-J. Hou, G.-S. Wu, Y.-Y. Xu, H.-W. Xiang, H. Jiao, and Y.-W. Li J. Phys. Chem. A 106 2002 7184
65. Y.-M. Sun, H.-Y. Zhang, and D.-Z. Chen Chin. J. Chem. 19 2001 657
66. J.-M. Lue, J.M. Wittbrodt, K. Wang, Z. Wen, H.B. Schlegel, P.G. Wang, and J.-P. Cheng J. Am. Chem. Soc. 123 2001 2903
67. Y.-F. Zhang, S.-C. Xiang, and J.-Q. Li Acta Chim. Sinica 58 2000 962
68. A.K. Chandra, and T. Uchimaru J. Phys. Chem. A 104 2000 9244
69. G.A. DiLabio, and D.A. Pratt J. Phys. Chem. A 104 2000 1938
70. G.P.F. Wood, D.J. Henry, and L. Radom J. Phys. Chem. A 107 2003 7985
71. S.W. Benson Thermochemical Kinetics 2nd ed. 1976 Wiley New York
72. F. Wang, X.-J. Xu, H.-M. Xiao, and J. Zhang J. Acta Chim. Sinica 61 2003 1939
73. K.B. Clark, P.N. Culshaw, D. Griller, F.P. Lossing, and M.J.A. Simoes J. Org. Chem. 56 1991 5535
74. G. Leroy J. Mol. Struct. 120 1985 91
75. P. von R. Schleyer, F.D. Jemmis, and G.W. Spitznagel J. Am. Chem. Soc. 107 1985 6393
76. Y.-D. Wu, W. Kirmse, and K.N. Houk J. Am. Chem. Soc. 112 1990 4557
77. K.B. Wiberg, and P.R. Rablen J. Am. Chem. Soc. 115 1993 614
78. The idea of calculating extra stabilization effects was proposed before. See: G. Leroy, J.-P. Dewispelaere, H. Benkadour, D.R. Temsamani, and C. Wilante Bull. Soc. Chim. Belg. 103 1994 367
79. R.W. Baldock, P. Hudson, A.R. Katritzky, and F. Soti J. Chem. Soc., Perkin Trans. 1 1974 1422
80. A.R. Katritzky, P.A. Shipkova, M. Qi, D. Nichols, R.D. Burton, C.H. Waston, J.R. Eyler, T. Tamm, M. Karelson, and M.C. Zerner J. Am. Chem. Soc. 118 1996 11905
81. J.P. Cheng, H.X. Wang, Z.W. Huan, C.E. Tan, and J.A. Landgrebe Chem. J. Chin. Univ. 18 1997 1067
82. S.Q. Zhang, J.K. Feng, A.M. Ren, and Y.X. Li Chem. J. Chin. Univ. 23 2002 1772
83. M.J.S. Dewar J. Am. Chem. Soc. 74 1952 3353
84. L. Stella, Z. Janousek, R. Merenyi, and H.G. Viehe Angew. Chem., Int. Ed. Engl. 17 1978 691
85. G. Leroy, J.-P. Dewispelaere, H. Benkadour, D.R. Temsamani, and C. Wilante J. Mol. Struct. (Theochem) 334 1995 137
86. A.E. Reed, L.A. Curtiss, and F. Weinhold Chem. Rev. 88 1988 899
87. A.J. Kirby Stereoelectronic Effects 1996 Oxford Science Oxford
88. X.P. Nie, and X.L. Ye Chin. J. Org. Chem. 19 1999 109