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

doi:10.1007/s40242-014-4012-3

Abstract

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.

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]. Chemical Research in Chinese Universities, 2014, 30(3): 455-460.

References

[1] Xu J. Z., Shen J., Cheng Y. Y., Qu H. B., Chem. Res. Chinese Universities, 2009, 25(6), 812
[2] Zhang H. T., Wu D., Zhang L. X., Chem. Res. Chinese Universities, 2008, 24(4), 516
[3] Lacivita E., Leopoldo M., De Giorgio P., Berardi F., Perrone R., Bioorg. Med. Chem., 2009, 17(3), 1339
[4] Avdeef A., Curr. Top. Med. Chem., 2001, 1(75), 277
[5] Tauada M., Faust R., Macromol., 2005, 38(12), 4989
[6] Soskic V., Joksimovic J., Curr. Med. Chem., 1998, 5(4), 493
[7] Rosini M., Bolognesi M. L., Giardina D., Minarini A., Tumiatti V., Melchiorre C., Curr. Top. Med. Chem., 2007, 7(2), 147
[8] Lopez-Rodriguez M. L., Ayala D., Benhamu B., Morbillo M. J., Viso A., Curr. Med. Chem., 2002, 9(8), 811
[9] Li D. M., Huang X. Q., Han K. L., Zhan C. G., J. Am. Chem. Soc., 2011, 133(19), 7416
[10] Li D. M., Wang Y., Yang C. L., Han K. L., Dalton Trans., 2009, (2), 291
[11] Song K. Z., Ma J. J., Wang X., Gong P., Zhao Y. F., Chem. Res. Chinese Universities, 2014, 30(1), 75
[12] Blassco A., Bunton C. A., Bunel S., Ibarra C., Moraga E., Cell, 1997, 163(1), 25
[13] Poole S. K., Patel S., Dehring K., Workman H., Poole C. F., J. Chromatogr. A, 2004, 1037(3), 445
[14] Lachenwizer A., Li N., Lipkowski J., J. Electroanal. Chem., 2002, 532(1/2), 85
[15] Rouhani S., Rezaei R., Sharghi H., Shamsipur M., Rounaghi G., Microchem. J., 1995, 52(1), 22
[16] Moghimi A., Alizadeh R., Shokrollahi A., Aghabozorg H., Shamsipur M., Shockravi A., Inorg. Chem., 2003, 42(5), 1616
[17] Pliego J. R., Riveros J. M., J. Phys. Chem. A, 2002, 106(32), 7434
[18] Fu Y., Liu L., Li R. Q., Liu R., Guo Q. X., J. Am. Chem. Soc., 2004, 126(3), 814
[19] Samir A., Senior A. M., Int. J. Quantum Chem., 2012, 112(3), 683
[20] Rayne S., Forest K., J. Mol. Struct.(Theohem.), 2010, 949(3), 60
[21] Casasnovas R., Fernandez D., Ortega-Castro J., Frau J., Donoso J., Munoz F. T., Theor. Chem. Acc., 2011, 130(1), 1
[22] Lu H. T., Chen X., Zhan C. G., J. Phys. Chem. B, 2007, 111(35), 10599
[23] Nagy P. I., Maheshwari A., Kim Y. W., Messer W. S., J. Phys. Chem. B, 2010, 114(1), 349
[24] Kiani F., Rostami A. A., Sharifi S., Bahadori A., Chaichi M. J., J. Chem. Eng. Data, 2010, 55(3), 2732
[25] Bahers T. L., Adamo C., Ciofini I., Chem. Phys. Lett., 2009, 472(6), 30
[26] Sharma I., Kaminski G. A., J. Comput. Chem., 2012, 33(30), 2388
[27] Khalili F., Henni A., East A. L. L., J. Mol. Struct.(Theochem.), 2009, 916(1―3), 1
[28] Zanganeh J., Altarawneh M., Saraireh I., Namazi S., Zanganeh J., Comput. Theor. Chem., 2013, 1011(2), 21
[29] Sastre S., Casasnovas R., Muñoz F., Frau J., Theor. Chem. Acc., 2013, 132(27), 1310
[30] Fu Y., Liu L., Li R., Liu R., Guo Q., J. Am. Chem. Soc., 2004, 126(28), 814
[31] Magill A. M., Cavell K. J., Yates B. F., J. Am. Chem. Soc., 2004, 126(28), 8717
[32] Ochterski J. W., Petersson G. A., Montgomery J. A., J. Chem. Phys., 1996, 104(7), 2598
[33] Montgomery J. A., Frisch J. M. J., Ochterski J. W., Petersson J. A., J. Chem. Phys., 1999, 110(6), 2822
[34] Montgomery J. A., Frisch M. J., Ochterski J. W., Petersson G. A., J. Chem. Phys., 2000, 112(14), 6532
[35] Curtiss L. A., Raghavachari K., Redfern P. C., Rassolov V., Pople J. A., J. Chem. Phys., 1998, 109(18), 7764
[36] Baboul A. G., Curtiss L. A., Redfern P. C., Raghavachari K., J. Chem. Phys., 1999, 110(16), 7650
[37] Curtiss L. A., Redfern P. C., Raghavachari K., Rassolov V., Pople J. A., J. Chem. Phys., 1999, 110(10), 4703
[38] Curtiss L. A., Redfern P. C., Raghavachari K., J. Chem. Phys., 2007, 127(12), 124105
[39] Curtiss L. A., Redfern P. C., Raghavachari K., J. Chem. Phys., 2007, 126(18), 184108
[40] Ho J., Coote M. L., Theor. Chem. Acc., 2010, 125(2), 3
[41] Liptak M. D., Shields G. C., J. Am. Chem. Soc., 2001, 123(30), 7314
[42] Liptak M. D., Gross K. C., Seybold P. G., Feldgus S., Shields G. C., J. Am. Chem. Soc., 2002, 124(22), 6421
[43] Murlowska K., Sadlej-Sosnowska N., J. Phys. Chem. A, 2005, 109(25), 5590
[44] Mayuri G., Eirik F., Hallvard F., Energy Procedia., 2012, 23(10), 140
[45] Camaioni D. M., Schwerdtfeger C. A., J. Phys. Chem. A, 2005, 109(47), 10795
[46] Lim C., Bashford D., Karplus M., J. Phys. Chem., 1991, 95(14), 5610
[47] Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Montgomery J. A. Jr., Vreven T., Kudin K. N., Burant J. C., Millam J. M., Iyengar S. S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G.., Rega N., Petersson G. A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J. E., Hratchian H. P., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Ayala P. Y., Morokuma K., Voth G. A., Salvador P., Dannenberg J. J., Zakrzewski V. G., Dapprich S., Daniels A. D., Strain M. C., Farkas O., Malick D. K., Rabuck A. D., Raghavachari K., Foresman J. B., Ortiz J. V., Cui Q., Baboul A. G., Clifford S., Cioslowski J., Stefanov B. B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R. L., Fox D. J., Keith T., Al-Laham M. A., Peng C. Y., Nanayakkara A., Challacombe M., Gill P. M. W., Johnson B., Chen W., Wong M. W., Gonzalez C., Pople J. A., Gaussian 03, Revision E.01, Gaussian Inc., Wallingford CT, 2004
[48] Becke A. D., J. Chem. Phys., 1986, 84(8), 4524
[49] Becke A. D., J. Chem. Phys., 1994, 100(1), 45
[50] Lee C., Yang W., Parr R. G., Phys. Rev. B, 1998, 37(2), 785
[51] Becke A. D., Phys. Rev. A, 1998, 38(6), 3098
[52] Perdew J. P., Wang Y., Phys. Rev. B, 1992, 45(23), 13244
[53] Dunning T. H., J. Chem. Phys., 1998, 90(2), 1007
[54] Barone V., Cossi M., J. Phys. Chem. A, 2000, 104(46), 10614
[55] Miertus S., Scrocco E., Tomasi J., J. Chem. Phys., 1981, 55(10), 117
[56] Miertus S., Tomasi J., J. Chem. Phys., 1982, 65(6), 239
[57] Cossi M., Barone V., Cammi R., Tomasi J., J. Chem. Phys. Lett., 1996, 255(16), 327
[58] Clark T., Chandrasekhar G. W., Suitznaael G. W., Schleyer P. R., J. Comput. Chem., 1983, 4(3), 294
[59] Barone V., Cossi M., J. Phys. Chem. A, 1998, 102(11), 1995
[60] Ghalami-Choobar B., Dezhampanah H., Nikparsa P., Ghiami- Shomami A., Int. J. Quantum Chem., 2012, 112, 2275

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

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