Citation:
ZHENG Wen-Rui, XU Jing-Li, XIONG Rui. Density Functional Theory Study on N—O Bond Dissociation Enthalpies[J]. Acta Physico-Chimica Sinica,
;2010, 26(09): 2535-2542.
doi:
10.3866/PKU.WHXB20100931
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A number of density functional theory (DFT) methods were compared for the calculation of N—O bond dissociation enthalpies (BDEs) with the experimental values on the basis of the high-precision calculation methods G3 and G3B3. We found that the B3P86 method gave the lowest root of mean square error of 6.36 kJ·mol-1 for calculating N—O BDE of 15 molecules and the correlation coefficient between the theoretical and experimental values was 0.991. We, therefore, used this method to calculate the N—O BDEs of non-aromatic and aromatic compounds. Using natural bond orbital analysis, quantitative relationships between some N—O BDEs and the corresponding N—O bond lengths, atomic charges, bond orders were determined. In addition, we predicted the N—O BDEs of several typical heterocyclic aromatic compounds using the B3P86 method.
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[1]
1. (a) Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem., 1994, 98: 2744
-
[2]
(b) Zhu, X. Q.; Li, H. R.; Ai, T.; Lu, J. Y.; Yang, Y.; Cheng, J. P. Chem.-Eur. J., 2003, 9: 871
-
[3]
2. (a) Bordwell, F. H.; Zhang, X. M. Acc. Chem. Res., 1993, 26: 510
-
[4]
(b) Larhoven, L. J. J.; Mulder, P.;Wayner, D. D. M. Acc. Chem. Res., 1999, 32: 342
-
[5]
3. (a) Sun, Y. M.; Zhang, H. Y.; Chen, D. Z.; Liu, C. B. Org. Lett., 2002, 4: 2909
-
[6]
(b) Wang, L. F.; Zhang, H. Y. Bioorg. Med. Chem. Lett., 2003, 13: 3789
-
[7]
(c) Yao, X. Q.; Hou, X. J.; Jiao, H.; Xiang, H. M.; Li, Y. W. J. Phys. Chem. A, 2003, 107: 9991
-
[8]
(d) Turecek, F. J. Am. Chem. Soc., 2003, 125: 5954 (e) Shen, L.; Zhang, H. Y.; Ji, H. F. Org. Lett., 2005, 7: 243
-
[9]
4. (a) Feng, Y.; Liu, L.; Wang, J. T.; Huang, H.; Guo, Q. X. J. Chem. Inf. Comput. Sci., 2003, 43: 2005
-
[10]
(b) Qi, X. J.; Li, Z.; Fu, Y.; Guo, Q. X.; Liu, L. Organometallics, 2008, 27: 2688
-
[11]
5. (a) Henry, D. J.; Parkinson, C. J.; Mayer, P. M.; Radom, L. J. Phys. Chem. A, 2001, 105: 6750
-
[12]
(b) Song, K. S.; Cheng, Y. H.; Fu, Y.; Liu, L.; Li, X. S.; Guo, Q. X. J. Phys. Chem. A, 2002, 106: 6651
-
[13]
6. (a) Pratt, D. A.; Mills, J. H.; Porter, N. A. J. Am. Chem. Soc., 2003, 125: 5801
-
[14]
(b) Zhang, H. Y.; Sun, Y. M.; Wang, X. L. Chem. Eur. J., 2003, 9: 502
-
[15]
(c) Lin, C. L.; Lai, C. H.; Chu, S. Y. Chem. Phys. Lett., 2002, 359: 355
-
[16]
(d) Zhang, H. Y.; Sun, Y. M.; Chen, D. Z. Chin. Chem. Lett., 2002, 13: 531
-
[17]
(e) Yao, X. Q.; Hou, X. J.; Wu, G. S.; Xu, Y. Y.; Xiang, H. W.; Jiao, H.; Li, Y. W. J. Phys. Chem. A, 2002, 106: 7184
-
[18]
(f) Lue, J. M.;Wittbrodt, J. M.;Wang, K.; Wen, Z.; Schlegel, H. B.; Wang, P. G.; Cheng, J. P. J. Am. Chem. Soc., 2001, 123: 2903
-
[19]
(g) Feng, Y.; Liu, L.; Wang, J. T.; Zhao, S. W.; Guo, Q. X. J. Org. Chem., 2004, 69: 3129
-
[20]
7. mes, J. R. B.; Ribeiro da Silva, M. D. M. C.; Ribeiro da Silva, M. A. V. Chem. Phys. Lett., 2006, 429: 18
-
[21]
8. Luo, Y. R. Handbook of bond dissociation energies. Beijing: Science Press, 2005: 212-219
-
[22]
[罗渝然. 化学键能数据手册. 北京: 科学出版社, 2005: 212-219]
-
[23]
9. Acree Jr.,W. E.; Tucker, S. A.; Ribeiro da Silva, M. D. M. C.; Matos, M. A. R.; ncalves, J. M.; Ribeiro da Silva, M. A. V.; Pilcher, G. J. Chem. Thermody., 1995, 27: 391
-
[24]
10. mes, J. R. B.; Sousa, E. A.; ncalves, J. M.; Monte, M. J. S.; mes, P.; Pandey, S.; Acree Jr.,W. E.; Ribeiro da Silva, M. D. M. C. J. Phys. Chem. B, 2005, 109: 16188
-
[25]
11. Ribeiro da Silva, M. D. M. C.; mes, J. R. B.; ncalves, J. M.; Sousa, E. A.; Pandey, S.; Acree Jr.,W. E. Org. Biomol. Chem., 2004, 2: 2507
-
[26]
12. Ribeiro da Silva, M. D. M. C.; mes, J. R. B.; ncalves, J. M.; Sousa, E. A.; Pandey, S.; Acree Jr., W. E. J. Org. Chem., 2004, 69: 2785
-
[27]
13. (a) Becke, A. D. Phys. Rev. A, 1988, 38: 3098 (b) Lee, C.; Yang,W.; Parr, R. G. Phys. Rev. B, 1988, 37: 785
-
[28]
14. Xu, X.; ddard, W. A. Proc. Natl. Acad. Sci. U. S. A., 2004, 101: 2673
-
[29]
15. Boese, A. D.; Martin, J. M. L. J. Chem. Phys., 2004, 121: 3405
-
[30]
16. Perdew, J. P. Phys. Rev. B, 1986, 33: 8822
-
[31]
17. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A, 2004, 108: 6908
-
[32]
18. Dahlke, E. E.; Truhlar, D. G. J. Phys. Chem. B, 2005, 109: 15677
-
[33]
19. Zhao, Y.; Truhlar, D. G. Phys. Chem. Chem. Phys., 2005, 7: 2701
-
[34]
20. Lynch, B. J.; Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A, 2003, 107: 1384
-
[35]
21. Zhao, Y.; nzalez-Garcia, N.; Truhlar, D. G. J. Phys. Chem. A, 2005, 109: 2012
-
[36]
22. Grimme, S. J. Chem. Phys., 2006, 124: 10342
-
[37]
23. Schwabe, T.; Grimme, S. Phys. Chem. Chem. Phys., 2006, 8: 4398
-
[38]
24. Kang, J. K.; Musgrave, C. B. J. Chem. Phys., 2001, 115: 11040
-
[39]
25. Perdew, J. P.; Burke, K.; Wang, Y. Phys. Rev. B, 1996, 54: 16533
-
[40]
26. Hoe, W. M.; Cohen, A. J.; Handy, N. C. Chem. Phys. Lett., 2001, 341: 319
-
[41]
27. Schultz-Fademrecht, C.; Tius, M. A.; Grimme, S.; Wibbeling, B.; Hoppe, D. Angew. Chem. Int. Edit., 2002, 41: 1532
-
[42]
28. (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev., 1988, 88: 899
-
[43]
(b) Cheng, Y. H.; Zhao, X.; Song, K. S.; Liu, L.; Guo, Q. X. J. Org. Chem., 2002, 67: 6638
-
[44]
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; et al. Gaussian 03. Revision A.01. Pittsburgh, PA: Gaussian Inc., 2003
-
[45]
30. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. J. Chem. Phys., 1998, 109: 7764
-
[46]
31. Baboul, A. G.; Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. J. Chem. Phys., 1999, 110: 7650
-
[47]
32. Zheng, W. R.; Fu, Y.; Wang, H. J.; Guo, Q. X. Chin. J. Org. Chem., 2008, 28: 459
-
[48]
[郑文锐,傅尧,王华静,郭庆祥. 有机化学, 2008, 28: 459]
-
[49]
33. Acree Jr., W. E.; Pilcher, G.; Ribeiro da Silva, M. D. M. C. J. Phys. Chem. Ref. Data, 2005, 34: 553
-
[50]
34. Glendening, E. D.;Weinhold, F. J. Comput. Chem., 1998, 19: 610
-
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