Citation: ZHOU Zi-Yan, LIU Min, SU Zhong-Min, XIE Yu-Zhong, DING Shen-De, WANG Hua-Jing. Proton-Transfer Isomerization Reactions of 2-(2-Hydroxybenzylidenamino)pyrimidine-4,6-diol[J]. Acta Physico-Chimica Sinica, ;2011, 27(09): 2035-2042. doi: 10.3866/PKU.WHXB20110903 shu

Proton-Transfer Isomerization Reactions of 2-(2-Hydroxybenzylidenamino)pyrimidine-4,6-diol

1.
1. College of Chemical Engineering, Shandong University of Technology, Zibo 255049, Shandong Province, P. R. China;
2. Institute of Functional Material Chemistry, Faculty of Chemistry, Northeast Normal University, Changchun 130024, P. R. China;
3. Department of Chemistry, College of Science, Yanbian University, Yanji 133002, Jilin Province, P. R. China

Received Date: 28 February 2011
Available Online: 4 July 2011
Fund Project: 国家自然科学基金(20703008) (20703008)山东省自然科学基金(ZR2009BL024)资助项目 (ZR2009BL024)

To determine the tautomerism mechanism between the enol form and the keto form of 2- (2-hydroxybenzylidenamino)pyrimidine-4,6-diol (M1) the potential energy surface of the isomerization was studied using density functional theory (DFT) calculations at the B3LYP/6-311+G(d, p) level. We found that there were at least 8 isomers and 10 transition states in the possible reaction pathways. All the possible processes of the reaction were studied. The results showed that the energy of 6-hydroxy-2-(2- hydroxybenzylideneamino) pyrimidine-4(3H)-one (M6) was lower than those of the other isomers in the form of a monomer, a hydrate, and a dimer. Therefore, it was the most stable isomer. In these possible reaction pathways the activation free energy required for intramolecular prototropy was 143.8 kJ·mol^-1 and for the proton transfer process that was catalyzed by water was 38.9 kJ·mol^-1. The activation free energy in the double-proton transfer of the dimer was 0.6 kJ·mol^-1, which was the lowest value. The latter pathway was feasible at room temperature. This implies that hydrogen bonding plays an important role in depressing the activation energy of the reaction.
- 2-(2-Hydroxybenzylidenamino)pyrimidine)-4,6-diol,
- Density functional theory,
- Tautomerism,
- Proton transfer
1. [1]
  (1) Hadjoudis, E.; Dziembowska, T.; Rozwadowski, Z. J. Photoch. Photobio. A 1999, 128, 97.
2. [2]
  (2) Kunkely, H.; Vogler, A. J. Photoch. Photobio. A 2001, 138, 51.
3. [3]
  (3) Gazivoda, T.; Plevnik, M.; Plavec, J.; Kraljevi?, S.; Kralj, M.; Paveli?, K.; Balzarini, J.; De Clercq, E.; Mintas, M.; Rai?- Mali?, S. Bio. Med. Chem. 2005, 13 (1), 131.
4. [4]
  (4) Huang, Y. Q.; Kenttämaa, H. J. Phys. Chem. A 2003, 107 (24), 4893.
5. [5]
  (5) Peng, H. L.; Yu, X. Y.; Yi, P. G.;Wang, Z. X.; Li, X. F.;Wang, T.; Zhou, J. M. Acta Phys. -Chim. Sin. 2010, 26 (1), 141. [彭洪亮, 于贤勇, 易平贵, 汪朝旭, 李筱芳, 王涛, 周继明. 物理化学学报, 2010, 26 (1), 141.]
6. [6]
  (6) Shi, J. Y.; Dong, L. H.; Liu, Y. J. Acta Phys. -Chim. Sin. 2010, 26 (12), 3329. [史俊友, 董丽花, 刘永军. 物理化学学报, 2010, 26 (12), 3329.]
7. [7]
  (7) Xu, X. F.; Gao, F.; Li, H. R.; Zhang, S. T. Acta Phys. -Chim. Sin. 2010, 26 (1), 131. [徐晓芳, 高芳, 李红茹, 张胜涛. 物理化学学报, 2010, 26 (1), 131.]
8. [8]
  (8) Wang, L. X.; Yi, D. H.; Zou, H. T.; Xu, J.; Xu,W. L. Acta Phys. -Chim. Sin. 2010, 26 (1), 149. [王罗新, 易第海, 邹汉涛, 许杰, 徐卫林. 物理化学学报, 2010, 26 (1), 149.]
9. [9]
  (9) Liu, Y. H.; Mehata, M. S.; Liu, J. Y. J. Phys. Chem. A 2011, 115, 19.
10. [10]
  (10) Zhao, X.; Chen, M. J. Phys. Chem. A 2010, 114, 7786.
11. [11]
  (11) Moser, A.; Range, K.; York, D. M. J. Phys. Chem. B 2010, 114, 13911.
12. [12]
  (12) Manoj, K. N. J. Photoch. Photobio. A 2011, 217, 40.
13. [13]
  (13) Li, A.; Yan, T.; Shen, P. J. Power Sources 2011, 196, 905.
14. [14]
  (14) Xia, S.W.; Xu, X.; Sun, Y. L.; Fan, Y. H.; Bi, C. F.; Zhang, D. M.; Yang, L. R. Chin. J. Struct. Chem. 2006, 25, 197.
15. [15]
  (15) Abdel-Latif, S. A.; Hassib, H. B.; Issa, Y. M. Spectrochim Acta A 2007, 67, 950.
16. [16]
  (16) Yu,W.; Yang, L.; Zhang, T. L.; Zhang, J. G.; Ren, F. J.; Liu, Y. H.;Wu, R. F.; Guo, J. Y. J. Mol. Struct. 2006, 794, 255.
17. [17]
  (17) Lang, H. Y.; Cai, J.; Shen, Y. H.; Jia, Y. Q. Acta Chimica Sinica 2005, 63, 814. [郎惠云, 蔡健, 申烨华, 贾璎琦. 化学学报, 2005, 63, 814.]
18. [18]
  (18) Koll, A.; Karpfen, A.;Wolschann, P. J. Mol. Struct. 2006, 790, 55.
19. [19]
  (19) Xiao, F. R.; Chen, L.;Wang, J. D.;Wu, R. L.; Yue, F.; Li, J. Acta Chimica Sinica 2006, 64, 1517. [肖芙蓉, 陈鹭, 王吉德, 武荣兰, 岳凡, 李静. 化学学报, 2006, 64, 1517.]
20. [20]
  (20) Makhmutova, R. I.; Vakulin, I. V.; Talipov, R. F.; Movsumzade, E. M.; Chuvashov, D. A. J. Mol. Struct.-Theochem 2007, 819, 21.
21. [21]
  (21) Ko?odziej, B.; Grech, E.; Schilf,W.; Kamienski, B.; Makowski, M.; Rozwadowski, Z.; Dziembowska, T. J. Mol. Struct. 2007, 32, 844.
22. [22]
  (22) Zhao, J. Y.; Zhou, Z. Y.; Su, Z. M.; Xie, Y. Z.; Sun, G. G.;Wu, X. Chin. J. Chem. 2006, 24 (6), 724.
23. [23]
  (23) Zhou, Z. Y.; Shan, G. G.; Zhu, Y. L.; Yu, X. J.; Dong, Y. H.; Zhao, J. Y. J. Struct. Chem. 2009, 50 (4), 606.
24. [24]
  (24) Zhou, Z. Y.; Zhao, J. Y.; Liu, M.; Su, Z. M.; Sun, G. Y. Chem. J. Chin. Univ. 2007, 28 (12), 2385. [周子彦, 赵继阳, 刘敏, 苏忠民, 孙光延. 高等学校化学学报, 2007, 28 (12), 2385.]
25. [25]
  (25) Zhao, J. Y.; Zhou, Z. Y.; Su, Z. M.; Xie, Y. Z.;Wu, X. Chem. J. Chin. Univ. 2006, 27 (3), 494. [赵继阳, 周子彦, 苏忠民, 谢玉忠, 吴学. 高等学校化学学报, 2006, 27 (3), 494.]
26. [26]
  (26) Zhou, Z. Y.; Shan, G. G.; Liao, Y.; Xing,W.; Yang, S.Y.; Su, Z. M. J. Mol. Struct.-Theochem 2010, 945, 110.
27. [27]
  (27) Cherayath, S.; Alice J.; Chathakudam, P. P. Transition Metal Chem. 1990, 15, 449.
28. [28]
  (28) Francisco, H. U.; Nuria, A. I. C.; Miguel, N. M. C.; Jose, M. M. M.; Maria, J. R. E. J. Inorg. Biochem. 2003, 94, 326.
29. [29]
  (29) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al . Gaussian 03, Revision B.03; Gaussian Inc: Pittsburgh, PA, 2003.
30. [30]
  (30) Chen,W. K.; Xu, J.; Zhang, Y. F.; Zhou, L. X.; Li, J. J. Acta Phys. -Chim. Sin. 2002, 18, 802. [陈文凯, 许娇, 章永凡, 周立新, 李俊篯. 物理化学学报, 2002, 18, 802.]
31. [31]
  (31) Li, Q.; Huang, F. Q. Acta Phys. -Chim. Sin. 2005, 21, 52. [李权, 黄方千. 物理化学学报, 2005, 21, 52.]
32. [32]
  (32) Sun, X. M.;Wei, X. G,.;Wu, X. P.; Ren, Y.;Wong, N. B.; Li,W. K. J. Phys. Chem. A 2010, 114 (1), 595.
33. [33]
  (33) Sun, X. M.;Wei, X. G.;Wu, X. P.; Ren, Y.;Wong, N. B.; Li,W. K. Theor. Chem. Acc. 2010, 127, 493.
34. [34]
  (34) Deng, C.;Wu, X. P.; Sun, X. M.; Ren, Y.; Sheng, Y. H. J. Comput. Chem. 2009, 30, 285.
35. [35]
  (35) Jin, H.W.; Feng, J. K.; Ren, A. M.; Li, Z. R.;Wang, Z. Q.; Zhang, X. Acta Chimica Sinica 2000, 58, 194. [金宏威, 封继康, 任爱民, 李志儒, 王志强, 张希. 化学学报, 2000, 58, 194.]
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