Citation: MENG Xiang-Jun. Proton Transfer Mechanism of Alanine Induced by Zn²⁺: a Theoretical Study[J]. Chinese Journal of Structural Chemistry, ;2014, 33(5): 669-675. shu

Proton Transfer Mechanism of Alanine Induced by Zn²⁺: a Theoretical Study

MENG Xiang-Jun ^,

1.
Department of Chemistry, Tangshan Normal University, Tangshan 063000, China

Corresponding author: MENG Xiang-Jun,
Received Date: 13 August 2013
Available Online: 20 March 2014
Fund Project: Science Foundation of Tangshan Normal University (2013D02) (12150224B-2)

In this paper, proton transfer mechanism of alanine induced by Zn²⁺ was investigated by the CCSD/6-31++G**//B3LYP/6-31++G** method. Six neutral complexes and one amphoteric complex were optimized, among which the amphoteric complex was the most stable with binding energy of 201.92 kcal·mol^-1. In addition, the rotation of intramolecular single bond leads to the neutral configuration conversion, in which the rotation energy barriers of C-C single bonds are lower than 10.51 kcal·mol^-1, and those of C-O single bonds range among 9.53~17.50 kcal·mol^-1. On the other hand, the proton transfers among the carboxylic oxygen atoms can also result in the neutral configuration conversion, whose energy barriers of forward/back reaction are 53.90 and 32.46 kcal·mol^-1, respectively. In detail, the proton transfers from carboxylic group to amino lead to their configuration conversion from neutral to amphoteric. Furthermore, under the catalysis of Zn²⁺, there was no energy barrier in this reaction. The conversion route from the most stable neutral configuration Ⅱ to the most stable amphoteric configuration Ⅰ was: Ⅱ→Ⅱ-Ⅲ→Ⅲ→Ⅲ-Ⅵ→Ⅵ→Ⅴ-Ⅵ→Ⅴ→Ⅰ-Ⅴ→Ⅰ, with the energy barrier to be 64.64 kcal·mol^-1.
- complexes,
- alanine,
- Zn²⁺,
- transition state,
- reaction route,
- mechanism
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