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 shu

Density Functional Theory Study on N—O Bond Dissociation Enthalpies

1.
College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, P. R. China

Received Date: 4 May 2010
Available Online: 22 July 2010
Fund Project: 上海优青科研基金(B-8500-08-0110) (B-8500-08-0110)校启基金(08-22) (08-22)创新项目基金(cx0904009)资助项目 (cx0904009)

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.
- Density functional theory,
- Bond dissociation enthalpy,
- Natural bond orbital analysis,
- N—O bond
1. [1]
  
  1. (a) Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem., 1994, 98: 2744
2. [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. [3]
  2. (a) Bordwell, F. H.; Zhang, X. M. Acc. Chem. Res., 1993, 26: 510
4. [4]
  (b) Larhoven, L. J. J.; Mulder, P.;Wayner, D. D. M. Acc. Chem. Res., 1999, 32: 342
5. [5]
  3. (a) Sun, Y. M.; Zhang, H. Y.; Chen, D. Z.; Liu, C. B. Org. Lett., 2002, 4: 2909
6. [6]
  (b) Wang, L. F.; Zhang, H. Y. Bioorg. Med. Chem. Lett., 2003, 13: 3789
7. [7]
  (c) Yao, X. Q.; Hou, X. J.; Jiao, H.; Xiang, H. M.; Li, Y. W. J. Phys. Chem. A, 2003, 107: 9991
8. [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. [9]
  4. (a) Feng, Y.; Liu, L.; Wang, J. T.; Huang, H.; Guo, Q. X. J. Chem. Inf. Comput. Sci., 2003, 43: 2005
10. [10]
  (b) Qi, X. J.; Li, Z.; Fu, Y.; Guo, Q. X.; Liu, L. Organometallics, 2008, 27: 2688
11. [11]
  5. (a) Henry, D. J.; Parkinson, C. J.; Mayer, P. M.; Radom, L. J. Phys. Chem. A, 2001, 105: 6750
12. [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. [13]
  6. (a) Pratt, D. A.; Mills, J. H.; Porter, N. A. J. Am. Chem. Soc., 2003, 125: 5801
14. [14]
  (b) Zhang, H. Y.; Sun, Y. M.; Wang, X. L. Chem. Eur. J., 2003, 9: 502
15. [15]
  (c) Lin, C. L.; Lai, C. H.; Chu, S. Y. Chem. Phys. Lett., 2002, 359: 355
16. [16]
  (d) Zhang, H. Y.; Sun, Y. M.; Chen, D. Z. Chin. Chem. Lett., 2002, 13: 531
17. [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. [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. [19]
  (g) Feng, Y.; Liu, L.; Wang, J. T.; Zhao, S. W.; Guo, Q. X. J. Org. Chem., 2004, 69: 3129
20. [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. [21]
  8. Luo, Y. R. Handbook of bond dissociation energies. Beijing: Science Press, 2005: 212-219
22. [22]
  [罗渝然. 化学键能数据手册. 北京: 科学出版社, 2005: 212-219]
23. [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. [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. [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. [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. [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. [28]
  14. Xu, X.; ddard, W. A. Proc. Natl. Acad. Sci. U. S. A., 2004, 101: 2673
29. [29]
  15. Boese, A. D.; Martin, J. M. L. J. Chem. Phys., 2004, 121: 3405
30. [30]
  16. Perdew, J. P. Phys. Rev. B, 1986, 33: 8822
31. [31]
  17. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A, 2004, 108: 6908
32. [32]
  18. Dahlke, E. E.; Truhlar, D. G. J. Phys. Chem. B, 2005, 109: 15677
33. [33]
  19. Zhao, Y.; Truhlar, D. G. Phys. Chem. Chem. Phys., 2005, 7: 2701
34. [34]
  20. Lynch, B. J.; Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A, 2003, 107: 1384
35. [35]
  21. Zhao, Y.; nzalez-Garcia, N.; Truhlar, D. G. J. Phys. Chem. A, 2005, 109: 2012
36. [36]
  22. Grimme, S. J. Chem. Phys., 2006, 124: 10342
37. [37]
  23. Schwabe, T.; Grimme, S. Phys. Chem. Chem. Phys., 2006, 8: 4398
38. [38]
  24. Kang, J. K.; Musgrave, C. B. J. Chem. Phys., 2001, 115: 11040
39. [39]
  25. Perdew, J. P.; Burke, K.; Wang, Y. Phys. Rev. B, 1996, 54: 16533
40. [40]
  26. Hoe, W. M.; Cohen, A. J.; Handy, N. C. Chem. Phys. Lett., 2001, 341: 319
41. [41]
  27. Schultz-Fademrecht, C.; Tius, M. A.; Grimme, S.; Wibbeling, B.; Hoppe, D. Angew. Chem. Int. Edit., 2002, 41: 1532
42. [42]
  28. (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev., 1988, 88: 899
43. [43]
  (b) Cheng, Y. H.; Zhao, X.; Song, K. S.; Liu, L.; Guo, Q. X. J. Org. Chem., 2002, 67: 6638
44. [44]
  29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; et al. Gaussian 03. Revision A.01. Pittsburgh, PA: Gaussian Inc., 2003
45. [45]
  30. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. J. Chem. Phys., 1998, 109: 7764
46. [46]
  31. Baboul, A. G.; Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. J. Chem. Phys., 1999, 110: 7650
47. [47]
  32. Zheng, W. R.; Fu, Y.; Wang, H. J.; Guo, Q. X. Chin. J. Org. Chem., 2008, 28: 459
48. [48]
  [郑文锐,傅尧,王华静,郭庆祥. 有机化学, 2008, 28: 459]
49. [49]
  33. Acree Jr., W. E.; Pilcher, G.; Ribeiro da Silva, M. D. M. C. J. Phys. Chem. Ref. Data, 2005, 34: 553
50. [50]
  34. Glendening, E. D.;Weinhold, F. J. Comput. Chem., 1998, 19: 610
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