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Theoretical calculations of the pK a values of 1-aryl-4-propylpiperazine drugs in aqueous solution

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Abstract

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.

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Authors and Affiliations

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

    Linlin Fan, Xin Yang, Zhiyue Tian, Xuekun Zhao, Ruixiang Li & Ying Xue

  2. State Key Laboratory of Biotherapy, Sichuan University, Chengdu, 610041, P. R. China

    Ying Xue

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  1. Linlin Fan
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  2. Xin Yang
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  3. Zhiyue Tian
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  4. Xuekun Zhao
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  5. Ruixiang Li
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Correspondence to Ying Xue.

Additional information

Supported by the National Natural Science Foundation of China(Nos.21173151, J1103315) and the National Basic Research Program of China(No.2011CB201202).

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Fan, L., Yang, X., Tian, Z. et al. Theoretical calculations of the pK a values of 1-aryl-4-propylpiperazine drugs in aqueous solution. Chem. Res. Chin. Univ. 30, 455–460 (2014). https://doi.org/10.1007/s40242-014-4012-3

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  • DOI: https://doi.org/10.1007/s40242-014-4012-3

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