N—O键解离焓的密度泛函理论研究

doi:10.3866/PKU.WHXB20100931

Abstract

Abstract:

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.

Key words: Density functional theory, Bond dissociation enthalpy, Natural bond orbital analysis, N—O bond

MSC2000:

O641

ZHENG Wen-Rui, XU Jing-Li, XIONG Rui. Density Functional Theory Study on N—O Bond Dissociation Enthalpies[J].Acta Phys. -Chim. Sin., 2010, 26(09): 2535-2542.

References

1. (a) Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem., 1994, 98: 2744
(b) Zhu, X. Q.; Li, H. R.; Ai, T.; Lu, J. Y.; Yang, Y.; Cheng, J. P. Chem.-Eur. J., 2003, 9: 871
2. (a) Bordwell, F. H.; Zhang, X. M. Acc. Chem. Res., 1993, 26: 510
(b) Larhoven, L. J. J.; Mulder, P.;Wayner, D. D. M. Acc. Chem. Res., 1999, 32: 342
3. (a) Sun, Y. M.; Zhang, H. Y.; Chen, D. Z.; Liu, C. B. Org. Lett., 2002, 4: 2909
(b) Wang, L. F.; Zhang, H. Y. Bioorg. Med. Chem. Lett., 2003, 13: 3789
(c) Yao, X. Q.; Hou, X. J.; Jiao, H.; Xiang, H. M.; Li, Y. W. J. Phys. Chem. A, 2003, 107: 9991
(d) Turecek, F. J. Am. Chem. Soc., 2003, 125: 5954 (e) Shen, L.; Zhang, H. Y.; Ji, H. F. Org. Lett., 2005, 7: 243
4. (a) Feng, Y.; Liu, L.; Wang, J. T.; Huang, H.; Guo, Q. X. J. Chem. Inf. Comput. Sci., 2003, 43: 2005
(b) Qi, X. J.; Li, Z.; Fu, Y.; Guo, Q. X.; Liu, L. Organometallics, 2008, 27: 2688
5. (a) Henry, D. J.; Parkinson, C. J.; Mayer, P. M.; Radom, L. J. Phys. Chem. A, 2001, 105: 6750
(b) Song, K. S.; Cheng, Y. H.; Fu, Y.; Liu, L.; Li, X. S.; Guo, Q. X. J. Phys. Chem. A, 2002, 106: 6651
6. (a) Pratt, D. A.; Mills, J. H.; Porter, N. A. J. Am. Chem. Soc., 2003, 125: 5801
(b) Zhang, H. Y.; Sun, Y. M.; Wang, X. L. Chem. Eur. J., 2003, 9: 502
(c) Lin, C. L.; Lai, C. H.; Chu, S. Y. Chem. Phys. Lett., 2002, 359: 355
(d) Zhang, H. Y.; Sun, Y. M.; Chen, D. Z. Chin. Chem. Lett., 2002, 13: 531
(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
(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
(g) Feng, Y.; Liu, L.; Wang, J. T.; Zhao, S. W.; Guo, Q. X. J. Org. Chem., 2004, 69: 3129
7. Gomes, J. R. B.; Ribeiro da Silva, M. D. M. C.; Ribeiro da Silva, M. A. V. Chem. Phys. Lett., 2006, 429: 18
8. Luo, Y. R. Handbook of bond dissociation energies. Beijing: Science Press, 2005: 212-219
[罗渝然. 化学键能数据手册. 北京: 科学出版社, 2005: 212-219]
9. Acree Jr.,W. E.; Tucker, S. A.; Ribeiro da Silva, M. D. M. C.; Matos, M. A. R.; Goncalves, J. M.; Ribeiro da Silva, M. A. V.; Pilcher, G. J. Chem. Thermody., 1995, 27: 391
10. Gomes, J. R. B.; Sousa, E. A.; Goncalves, J. M.; Monte, M. J. S.; Gomes, P.; Pandey, S.; Acree Jr.,W. E.; Ribeiro da Silva, M. D. M. C. J. Phys. Chem. B, 2005, 109: 16188
11. Ribeiro da Silva, M. D. M. C.; Gomes, J. R. B.; Goncalves, J. M.; Sousa, E. A.; Pandey, S.; Acree Jr.,W. E. Org. Biomol. Chem., 2004, 2: 2507
12. Ribeiro da Silva, M. D. M. C.; Gomes, J. R. B.; Goncalves, J. M.; Sousa, E. A.; Pandey, S.; Acree Jr., W. E. J. Org. Chem., 2004, 69: 2785
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
14. Xu, X.; Goddard, W. A. Proc. Natl. Acad. Sci. U. S. A., 2004, 101: 2673
15. Boese, A. D.; Martin, J. M. L. J. Chem. Phys., 2004, 121: 3405
16. Perdew, J. P. Phys. Rev. B, 1986, 33: 8822
17. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A, 2004, 108: 6908
18. Dahlke, E. E.; Truhlar, D. G. J. Phys. Chem. B, 2005, 109: 15677
19. Zhao, Y.; Truhlar, D. G. Phys. Chem. Chem. Phys., 2005, 7: 2701
20. Lynch, B. J.; Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A, 2003, 107: 1384
21. Zhao, Y.; Gonzalez-Garcia, N.; Truhlar, D. G. J. Phys. Chem. A, 2005, 109: 2012
22. Grimme, S. J. Chem. Phys., 2006, 124: 10342
23. Schwabe, T.; Grimme, S. Phys. Chem. Chem. Phys., 2006, 8: 4398
24. Kang, J. K.; Musgrave, C. B. J. Chem. Phys., 2001, 115: 11040
25. Perdew, J. P.; Burke, K.; Wang, Y. Phys. Rev. B, 1996, 54: 16533
26. Hoe, W. M.; Cohen, A. J.; Handy, N. C. Chem. Phys. Lett., 2001, 341: 319
27. Schultz-Fademrecht, C.; Tius, M. A.; Grimme, S.; Wibbeling, B.; Hoppe, D. Angew. Chem. Int. Edit., 2002, 41: 1532
28. (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev., 1988, 88: 899
(b) Cheng, Y. H.; Zhao, X.; Song, K. S.; Liu, L.; Guo, Q. X. J. Org. Chem., 2002, 67: 6638
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; et al. Gaussian 03. Revision A.01. Pittsburgh, PA: Gaussian Inc., 2003
30. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Rassolov, V.; Pople, J. A. J. Chem. Phys., 1998, 109: 7764
31. Baboul, A. G.; Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. J. Chem. Phys., 1999, 110: 7650
32. Zheng, W. R.; Fu, Y.; Wang, H. J.; Guo, Q. X. Chin. J. Org. Chem., 2008, 28: 459
[郑文锐,傅尧,王华静,郭庆祥. 有机化学, 2008, 28: 459]
33. Acree Jr., W. E.; Pilcher, G.; Ribeiro da Silva, M. D. M. C. J. Phys. Chem. Ref. Data, 2005, 34: 553
34. Glendening, E. D.;Weinhold, F. J. Comput. Chem., 1998, 19: 610

[1]	Zhichao Huang,Yazhong Dai,Xiaojie Wen,Dan Liu,Yuxuan Lin,Zhen Xu,Jian Pei,Kai Wu. Conformational Switching of Verdazyl Radicals on Au(111) [J]. Acta Physico-Chimica Sinica, 2020, 36(1): 1907043-0.
[2]	Dan WANG,Xunlei DING,Henglu LIAO,Jiayu DAI. Methane Activation on (Au/Ag)₁-Doped Vanadium Oxide Clusters [J]. Acta Physico-Chimica Sinica, 2019, 35(9): 1005-1013.
[3]	Qiang CHEN,Li-Xue JIANG,Hai-Fang LI,Jiao-Jiao CHEN,Yan-Xia ZHAO,Sheng-Gui HE. Thermal Activation of Methane by Diatomic Vanadium Boride Cations [J]. Acta Physico-Chimica Sinica, 2019, 35(9): 1014-1020.
[4]	Mengru HAN,Yanan ZHOU,Xuan ZHOU,Wei CHU. Tunable Reactivity of MNi₁₂ (M = Fe, Co, Cu, Zn) Nanoparticles Supported on Graphitic Carbon Nitride in Methanation [J]. Acta Physico-Chimica Sinica, 2019, 35(8): 850-857.
[5]	Yue ZHAO,Jiatong CUI,Jichuang HU,Jiabi MA. Reactivities of VO_1–4⁺ Toward n-C_mH_2m+2 (m = 3, 5, 7) as Functions of Oxygen Content and Carbon Chain Length [J]. Acta Phys. -Chim. Sin., 2019, 35(5): 531-538.
[6]	Martínez GONZÁLEZ Marco,Carlos CÁRDENAS,Juan I. RODRÍGUEZ,Shubin LIU,Farnaz HEIDAR-ZADEH,Ramón Alain MIRANDA-QUINTANA,Paul W. AYERS. Quantitative Electrophilicity Measures [J]. Acta Phys. -Chim. Sin., 2018, 34(6): 662-674.
[7]	Paul W. AYERS,Mel LEVY. Levy Constrained Search in Fock Space: An Alternative Approach to Noninteger Electron Number [J]. Acta Phys. -Chim. Sin., 2018, 34(6): 625-630.
[8]	Tian LU,Qinxue CHEN. Revealing Molecular Electronic Structure via Analysis of Valence Electron Density [J]. Acta Phys. -Chim. Sin., 2018, 34(5): 503-513.
[9]	Farnaz HEIDAR-ZADEH,Paul W. AYERS. Generalized Hirshfeld Partitioning with Oriented and Promoted Proatoms [J]. Acta Phys. -Chim. Sin., 2018, 34(5): 514-518.
[10]	Yueqi YIN,Mengxu JIANG,Chunguang LIU. DFT Study of POM-Supported Single Atom Catalyst (M₁/POM, M = Ni, Pd, Pt, Cu, Ag, Au, POM = [PW₁₂O₄₀]^3-) for Activation of Nitrogen Molecules [J]. Acta Phys. -Chim. Sin., 2018, 34(3): 270-277.
[11]	Fanhua YIN,Kai TAN. Density Functional Theory Study on the Formation Mechanism of Isolated-Pentagon-Rule C₁₀₀(417)Cl₂₈ [J]. Acta Phys. -Chim. Sin., 2018, 34(3): 256-262.
[12]	Robert C MORRISON. Fukui Functions for the Temporary Anion Resonance States of Be^-, Mg^-, and Ca^- [J]. Acta Phys. -Chim. Sin., 2018, 34(3): 263-269.
[13]	Aiguo ZHONG,Rongrong LI,Qin HONG,Jie ZHANG,Dan CHEN. Understanding the Isomerization of Monosubstituted Alkanes from Energetic and Information-Theoretic Perspectives [J]. Acta Phys. -Chim. Sin., 2018, 34(3): 303-313.
[14]	Xinyi WANG,Lei XIE,Yuanqi DING,Xinyi YAO,Chi ZHANG,Huihui KONG,Likun WANG,Wei XU. Interactions between Bases and Metals on Au(111) under Ultrahigh Vacuum Conditions [J]. Acta Phys. -Chim. Sin., 2018, 34(12): 1321-1333.
[15]	Chi CHEN,Xue ZHANG,Zhi-You ZHOU,Xin-Sheng ZHANG,Shi-Gang SUN. Experimental Boosting of the Oxygen Reduction Activity of an Fe/N/C Catalyst by Sulfur Doping and Density Functional Theory Calculations [J]. Acta Phys. -Chim. Sin., 2017, 33(9): 1875-1883.

Density Functional Theory Study on N—O Bond Dissociation Enthalpies

PDF (PC)

Like

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Metrics

Comments

Recommended 0