Theoretical Calculations of the pKa Values of 1-Aryl-4-propylpiperazine Drugs in Aqueous Solution

doi:10.1007/s40242-014-4012-3

高等学校化学研究 ›› 2014, Vol. 30 ›› Issue (3): 455-460.doi: 10.1007/s40242-014-4012-3

Theoretical Calculations of the pK_a Values of 1-Aryl-4-propylpiperazine Drugs in Aqueous Solution

FAN Linlin¹, YANG Xin¹, TIAN Zhiyue¹, ZHAO Xuekun¹, LI Ruixiang¹, XUE Ying^1,2

1. Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China;
2. State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041, P. R. China

收稿日期:2014-01-09 修回日期:2014-04-03 出版日期:2014-06-01 发布日期:2014-04-14
通讯作者: XUE Ying E-mail:yxue@scu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(Nos.21173151, J1103315) and the National Basic Research Program of China(No.2011CB201202).

Theoretical Calculations of the pK_a Values of 1-Aryl-4-propylpiperazine Drugs in Aqueous Solution

FAN Linlin¹, YANG Xin¹, TIAN Zhiyue¹, ZHAO Xuekun¹, LI Ruixiang¹, XUE Ying^1,2

1. Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China;
2. State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041, P. R. China

Received:2014-01-09 Revised:2014-04-03 Online:2014-06-01 Published:2014-04-14
Contact: XUE Ying E-mail:yxue@scu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.21173151, J1103315) and the National Basic Research Program of China(No.2011CB201202).

摘要/Abstract

摘要：

Theoretical calculations were carried out to predict the aqueous-phase acidities of a series of drug 1-phenyl-4-propylpiperazine and its derivatives. The performances of the density functional theory(DFT) methods B3LYP and B3P86, solvation models[the polarized continuum model(PCM) and the conductor-like polarized continuum model(CPCM)], and the basis set effect were tested. A comparison between the theoretical and experimental pK_a values for para-substituted 1-phenyl-4-propylpiperazines reveals that the accuracy of B3LYP is better than that of B3P86, and the basis set 6-31++G(d,p) and the CPCM model are suitable for calculating pK_a values of the substituted 1-phenyl-4-propylpiperazine. For the investigated compounds, a reasonable agreement between the experimental and calculated pK_a values was also observed.

关键词: 1-Arylpiperazine, Aqueous pK_a, B3LYP, B3P86, Conductor-like polarized continuum model(CPCM)

Abstract:

Key words: 1-Arylpiperazine, Aqueous pK_a, B3LYP, B3P86, Conductor-like polarized continuum model(CPCM)

FAN Linlin, YANG Xin, TIAN Zhiyue, ZHAO Xuekun, LI Ruixiang, XUE Ying. Theoretical Calculations of the pK_a Values of 1-Aryl-4-propylpiperazine Drugs in Aqueous Solution[J]. 高等学校化学研究, 2014, 30(3): 455-460.

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Theoretical Calculations of the pK_a Values of 1-Aryl-4-propylpiperazine Drugs in Aqueous Solution

Theoretical Calculations of the pK_a Values of 1-Aryl-4-propylpiperazine Drugs in Aqueous Solution

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