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
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