Modern methods for estimation of ionization constants of organic compounds in solution

Russian Journal of Organic Chemistry

Volumn 47, Issue 10, 2011, Pages 1445-1467

  Zevatskii, Yu E ^a   Samoilov, D V ^b  

^a ST PETERSBURG STATE INSTITUTE OF TECHNOLOGY TECHNICAL UNIVERSITY   (Russian Federation)

^b Novbytkhim Close Corporation   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84856275825     PISSN: 10704280     EISSN: None     Source Type: Journal    
DOI: 10.1134/S1070428011100010     Document Type: Review

References (218)

1. Hammett, L., Physical Organic Chemistry, New York: McGraw-Hill, 1970, 2nd ed.
2. Izmailov, N.A., Elektrokhimiya rastvorov (Electrochemistry of Solutions), Khar'kov: Khar'kov. Gos. Univ., 1959.
3. Bell, R.P., The Proton in Chemistry, London: Chapman and Hall, 1973.
4. Pavlat, P., Hlavac, J., and Bekarek, V., Chem. Listy, 2005, vol. 99, p. 585.
5. Um, I.H., Hwang, S.J., and Buncel, E., J. Org. Chem., 2006, vol. 71, p. 915.
6. Pytela, O. and Kulhanek, J., Collect. Czech. Chem. Commun., 2002, vol. 67, p. 596.
7. IUPAC Compendium of Chemical Terminology; http://goldbook.iupac.org.
8. Cramer, C.J. and Truhlar, D.G., Solvent Effects and Chemical Reactivity, Tapia, O. and Bertran, J., Dordrecht: Kluwer Academic, 1996.
9. Houk, R.J.T., Monzingo, A., and Anslyn, E.V., Acc. Chem. Res., 2008, vol. 41, p. 401.
10. Trifonov, R.E. and Ostrovskii, V.A., Russ. J. Org. Chem., 2006, vol. 42, p. 1585.
11. Yagil, G., Tetrahedron, 1967, vol. 23, p. 2855.
12. Terekhova, M.I., Petrov, E.S., Rolina, E.M., Kravtsov, D.N., and Shatenshtein, A.I., Khim. Geterotsikl. Soedin., 1979, p. 1104.
13. Smith, M.B. and March, J., March's Advanced Organic Chemistry, New York: Wiley, 2001, 5th ed.
14. Emsley, J. and Freeman, N.J., J. Mol. Struct., 1987, vol. 161, p. 193.
15. Exner, O. and Kalfus, K., Collect. Czech. Chem. Commun., 1976, vol. 41, p. 569.
16. Kalfus, K., Friedl, Z., and Exner, O., Collect. Czech. Chem. Commun., 1984, vol. 49, p. 179.
17. Mchedlov-Petrosyan, N.O., Differentsirovanie sily organicheskikh kislot v istinnykh i organizovannykh rastvorakh (Differentiation of Strength of Organic Acids in True and Organized Solutions), Khar'kov: Khar'kov. Nats. Univ., 2004.
18. Reichardt, C., Solvents and Solvent Effects in Organic Chemistry, Weinheim: Wiley, 2003, 3rd ed.
19. Babic, S., Horvat, A.J.M., Mutavdzic-Pavlovic, D., and Kastelan-Macan, M., Trends Anal. Chem., 2007, vol. 26, p. 1043.
20. Lee, P.H., Ayyampalayam, S.N., Carreira, L.A., Shalaeva, M., Bhattachar, S., Coselmon, R., Poole, S., Gifford, E., and Lombardo, F., Mol. Pharm., 2007, vol. 4, p. 498.
21. Lee, P.H. and Rafferty, M.F., Mol. Pharm., 2007, vol. 4, p. 487.
22. Czodrowski, P., Sotriffer, C.A., and Klebe, G., J. Mol. Biol., 2007, vol. 367, p. 1347.
23. Nielsen, J.E., J. Mol. Graph. Model., 2007, vol. 25, p. 691.
24. Avdeef, B. and Testa, G., Cell. Mol. Life Sci., 2002, vol. 59, p. 1681.
25. Kirkwood, J.G. and Westheimer, F.H., J. Chem. Phys., 1938, vol. 6, p. 506.
26. Dyumaev, K.M. and Korolev, B.A., Usp. Khim., 1980, vol. 49, p. 2065.
27. Korolev, B.A. and Kashkovskaya, E.I., Zh. Obshch. Khim., 1979, vol. 49, p. 909.
28. Aleksandrov, V.V., Berezhnaya, T.A., Borodenko, V.I., and Kabakova, E.N., Khim. Fiz., 1996, vol. 15, p. 83.
29. Dulova, V.I., Molchanova, N.R., Gureeva, L.I., Gordienko, N.S., Skidan, N.A., Kalinichenko, L.T., Brezhe, A.L., and Grebenkina, V.N., Vest. Khar'kov. Gos. Univ., 1979, p. 21.
30. Pal'm, V.A., Osnovy kolichestvennoi teorii khimicheskikh reaktsii (Principles of Quantitative Theory of Chemical Reactions), Leningrad: Khimiya, 1977.
31. a Prediction for Organic Acids and Bases, London: Chapman and Hall, 1981.
32. Harris, J.C. and Hayes, M.J., Handbook of Chemical Property Estimation Methods: Environmental Behavior of Organic Compounds, Lyman, W.J., Reehl, W.F., and Rosenblatt, D.H., Eds., New York: McGraw-Hill, 1982.
33. Fraczkiewicz, R., Comprehensive Medicinal Chemistry II, Testa, B. and van de Waterbeemd, H., Eds., Boston: Elsevier, 2006, vol. 5, p. 603.
34. Bosch, E., Rived, F., Rosés, M., and Sales, J., J. Chem. Soc., Perkin Trans. 2, 1999, p. 1953.
35. Drago, R.S., Parr, L.B., and Chamberlain, C.S., J. Am. Chem. Soc., 1977, vol. 99, p. 3203.
36. Citra, M.J., Chemosphere, 1999, vol. 38, p. 191.
37. Pankratov, A.N. and Shalabai, A.V., Zh. Strukt. Khim., 2004, vol. 45, p. 800.
38. Pankratov, A.N., Uchaeva, I.M., Doronin, S.Yu., and Chernova, R.K., Zh. Strukt. Khim., 2001, vol. 42, p. 884.
39. Deakyne, C.A., Int. J. Mass Spectrom., 2003, vol. 227, p. 601.
40. Wright, J.S., Rowley, C.N., and Chepelev, L.L., Mol. Phys., 2005, vol. 103, p. 815.
41. Alongi, K.S. and Shields, G.C., Annu. Rep. Comput. Chem., 2010, vol. 6, p. 113.
42. Ho, J.-M. and Coote, M.L., Theor. Chem. Acc., 2010, vol. 125, p. 3.
43. Bryantsev, V.S., Diallo, M.S., and Goddard, W.A., J. Phys. Chem. A, 2007, vol. 111, p. 4422.
44. Fu, Y., Liu, L., Li, R.-Q., Liu, R., and Guo, Q.-X., J. Am. Chem. Soc., 2004, vol. 126, p. 814.
45. Chipman, D.M., J. Phys. Chem. A, 2002, vol. 106, p. 7413.
46. Meot-Ner, M., Int. J. Mass Spectrom., 2003, vol. 227, p. 525.
47. Range, K., Riccardi, D., Cui, Q., Elstnerc, M., and York, D.M., Phys. Chem. Chem. Phys., 2005, vol. 7, p. 3070.
48. Popelier, P.L.A. and Smith, P.J., Phys. Chem. Chem. Phys., 2001, vol. 3, p. 4208.
49. Ulander, J. and Broo, A., Int. J. Quantum Chem., 2005, vol. 105, p. 866.
50. Adam, K.R., J. Phys. Chem. A, 2002, vol. 106, p. 11 963.
51. Kallies, B. and Mitzner, R., J. Phys. Chem. B, 1997, vol. 101, p. 2959.
52. Jia, Z.-K., Du, D.-M., Zhou, Z.-Y., Zhang, A.-G., and Hou, R.-Y., Chem. Phys. Lett., 2007, vol. 439, p. 374.
53. Tao, L., Han, J., and Tao, F.-M., J. Phys. Chem. A, 2008, vol. 112, p. 775.
54. Zhang, S., Baker, J., and Pulay, P., J. Phys. Chem. A, 2010, vol. 114, p. 432.
55. Ding, F., Smith, J.M., and Wang, H., J. Org. Chem., 2009, vol. 74, p. 2679.
56. Eckert, F., Leito, I., Kaljurand, I., Kutt, A., Klamt, A., and Diedenhofen, M., J. Comput. Chem., 2009, vol. 30, p. 799.
57. Brown, T.N. and Mora-Diez, N., J. Phys. Chem. B, 2006, vol. 110, p. 20 546.
58. Han, J. and Tao. F.-M., J. Phys. Chem. A, 2006, vol. 110, p. 257.
59. Kelly, C.P., Cramer, C.J., and Truhlar, D.G., J. Phys. Chem. A, 2006, vol. 110, p. 2493.
60. Klamt, A., Eckert, F., Diedenhofen, M., and Beck, M.E., J. Phys. Chem. A, 2003, vol. 107, p. 9380.
61. Makowska, J., Makowski, M., and Chmurzynski, L., J. Phys. Chem. A, 2004, vol. 108, p. 10 354.
62. Schuurmann, G., Cossi, M., Barone, V., and Tomasi, J., J. Phys. Chem. A, 1998, vol. 102, p. 6706.
63. Pliego, J.R., Jr. and Riveros, J.M., Phys. Chem. Chem. Phys., 2002, vol. 4, p. 1622.
64. Pliego, J.R., Chem. Phys. Lett., 2003, vol. 381, p. 246.
65. Pliego, J.R., Chem. Phys. Lett., 2003, vol. 367, p. 145.
66. Bryantsev, V.S., Diallo, M.S., and Goddard, W.A., J. Phys. Chem. B, 2008, vol. 112, p. 9709.
67. Camaioni, D.M. and Schwerdtfeger, C.A., J. Phys. Chem. A, 2005, vol. 109, p. 10 795.
68. Klicic, J.J., Friesner, R.A., Liu, S.-Y., and Guida, W.C., J. Phys. Chem. A, 2002, vol. 106, p. 1327.
69. Sadlej-Sosnowska, N., Theor. Chem. Acc., 2007, vol. 118, p. 281.
70. Javier Luque, F., Curutchet, C., Munoz-Muriedas, J., Bidon-Chanal, A., Soteras, I., Morreale, A., Gelpi, J.L., and Orozco, M., Phys. Chem. Chem. Phys., 2003, vol. 5, p. 3827.
71. Takano, Y. and Houk, K.N., J. Chem. Theory Comput., 2005, vol. 1, p. 70.
72. Kelly, C.P., Cramer, C.J., and Truhlar, D.G., J. Phys. Chem. B., 2006, vol. 110, p. 16 066.
73. Cramer, C.J. and Truhlar, D.G., Acc. Chem. Res., 2008, vol. 41, p. 760.
74. Charif, I.E., Mekelleche, S.M., Villemin, D., and Mora-Diez, N., J. Mol. Struct. (Theochem), 2007, vol. 818, p. 1.
75. Liptak, M.D., Gross, K.C., Seybold, P.G., Feldgus, S., and Shields, G.C., J. Am. Chem. Soc., 2002, vol. 124, p. 6421.
76. Lu, H., Chen, X., and Zhan, C.-G., J. Phys. Chem. B, 2007, vol. 111, p. 10 599.
77. Murowska, K. and Sadlej-Sosnowska, N., J. Phys. Chem. A, 2005, vol. 109, p. 5590.
78. Namazian, M., Halvani, S., and Noorbala, M.R., J. Mol. Struct. (Theochem), 2004, vol. 711, p. 13.
79. Saracino, G.A.A., Improta, R., and Barone, V., Chem. Phys. Lett., 2003, vol. 373, p. 411.
80. Schmidt am Busch, M. and Knapp, E.-W., ChemPhysChem, 2004, vol. 5, p. 1513.
81. Toth, A.M., Liptak, M.D., Phillips, D.L., and Shields, G.C., J. Chem. Phys., 2001, vol. 114, p. 4595.
82. Zhang, S., Baker, J., and Pulay, P., J. Phys. Chem. A, 2010, vol. 114, p. 425.
83. Liptak, M.D. and Shields, G.C., J. Am. Chem. Soc., 2001, vol. 123, p. 7314.
84. Brown, T.N. and Mora-Diez, N., J. Phys. Chem. B, 2006, vol. 110, p. 9270.
85. Da Silva, C.O., da Silva, E.C., and Nascimento, M.A.C., J. Phys. Chem. A, 1999, vol. 103, p. 11 194.
86. Da Silva, C.O., da Silva, E.C., and Nascimento, M.A.C., J. Phys. Chem. A, 2000, vol. 104, p. 2402.
87. Almerindo, G.I., Tondo, D.W., and Pliego, J.R.J., J. Phys. Chem. A, 2004, vol. 108, p. 166.
88. Gutowski, K.E. and Dixon, D.A., J. Phys. Chem. A, 2006, vol. 110, p. 12 044.
89. Casasnovas, R., Frau, J., Ortega-Castro, J., Salva, A., Donoso, J., and Musoz, F., J. Mol. Struct. (Theochem), 2009, vol. 912, p. 5.
90. Tomasi, J., Mennucci, B., and Cammi, R., Chem. Rev., 2005, vol. 105, p. 2999.
91. Bondi, A., J. Phys. Chem., 1964, vol. 68, p. 441.
92. Ho, J.-M. and Coote, M.L., J. Chem. Theory Comput., 2009, vol. 5, p. 295.
93. Sang-Aroon, W. and Ruangpornvisuti, V., Int. J. Quantum Chem., 2008, vol. 108, p. 1181.
94. Yu, A., Liu, Y., and Wang, Y., Chem. Phys. Lett., 2007, vol. 436, p. 276.
95. Behjatmanesh-Ardakani, R., Karimi, M.A., and Ebady, A., J. Mol. Struct. (Theochem), 2009, vol. 910, p. 99.
96. Namazian, M. and Halvani, S., J. Chem. Thermodyn., 2006, vol. 38, p. 1495.
97. Namazian, M., Kalantary-Fotooh, F., Noorbala, M.R., Searles, D.J., and Coote, M.L., J. Mol. Struct. (Theochem), 2006, vol. 758, p. 275.
98. Jia, Z.K., Zhang, S.F., Zhou, Z.Y., Zhang, A.G., and Hou, R.Y., Int. J. Quantum Chem., 2008, vol. 108, p. 265.
99. Pliego, J.R. and Riveros, J.M., Jr., J. Phys. Chem. A, 2002, vol. 106, p. 7434.
100. Namazian, M. and Heidary, H., J. Mol. Struct. (Theochem), 2003, vol. 620, p. 257.
101. Tran, N.L. and Colvin, M.E., J. Mol. Struct. (Theochem), 2000, vol. 532, p. 127.
102. Kaminski, G.A., J. Phys. Chem. B, 2005, vol. 109, p. 5884.
103. Kawata, M., Ten-no, S., Kato, S., and Hirata, F., J. Phys. Chem., 1996, vol. 100, p. 1111.
104. Caballero, N.A., Melendez, F.J., Munoz-Caro, C., and Nino, A., Biophys. Chem., 2006, vol. 124, p. 155.
105. Namazian, M., Zakery, M., Noorbala, M.R., and Coote, M.L., Chem. Phys. Lett., 2008, vol. 451, p. 163.
106. Eckert, F., Diedenhofen, M., and Klamt, A., Mol. Phys., 2010, vol. 108, p. 229.
107. Foresman, J.B., Keith, T.A., Wiberg, K.B., Snoonian, J., and Frisch, M.J., J. Phys. Chem., 1996, vol. 100, p. 16 098.
108. Chen, I.J. and MacKerell, A.D., Theor. Chem. Acc., 2000, vol. 103, p. 483.
109. Bagno, A., Bujnicki, B., and Bertrand, S., Chemistry, 1999, vol. 5, p. 523.
110. Vianello, R. and Maksic, Z.B., Tetrahedron Lett., 2005, vol. 46, p. 3711.
111. Liu, J., Kelly, C.P., Goren, A.C., Marenich, A.V., Cramer, C.J., Truhlar, D.G., and Zhan, C.-G., J. Chem. Theory Comput., 2010, vol. 6, p. 1109.
112. Cramer, C.J. and Truhlar, D.G., Chem. Rev., 1999, vol. 99, p. 2161.
113. Soriano, E., Cerdan, S., and Ballesteros, P., J. Mol. Struct. (Theochem), 2004, vol. 684, p. 121.
114. Kelly, C.P., Cramer, C.J., and Truhlar, D.G., J. Chem. Theory Comput., 2005, vol. 1, p. 1133.
115. Klamt, A., Mennucci, B., Tomasi, J., Barone, V., Curutchet, C., Orozco, M., and Luque, F.J., Acc. Chem. Res., 2009, vol. 42, p. 489.
116. Magill, A.M., Cavell, K.J., and Yates, B.F., J. Am. Chem. Soc., 2004, vol. 126, p. 8717.
117. Lopez, X., Schaefer, M., Dejaegere, A., and Karplus, M., J. Am. Chem. Soc., 2002, vol. 124, p. 5010.
118. Dong, H., Du, H., and Qian, X., J. Phys. Chem. A, 2008, vol. 112, p. 12 687.
119. Jang, Y.H., Goddard, W.A., Noyes, K.T., Sowers, L.C., Hwang, S., and Chung, D.S., J. Phys. Chem. B, 2003, vol. 107, p. 344.
120. Czodrowski, P., Dramburg, I., Sotriffer, C.A., and Klebe, G., Proteins, 2006, vol. 65, p. 424.
121. Krieger, E., Nielsen, J.E., Spronk, C.A.E.M., and Vriend, G., J. Mol. Graph. Model., 2006, vol. 25, p. 481.
122. Riccardi, D., Schaefer, P., and Cui, Q., J. Phys. Chem. B, 2005, vol. 109, p. 11 715.
123. Carvalho, A.T.P., Fernandes, P.A., and Ramos, M.J., J. Comput. Chem., 2006, vol. 27, p. 966.
124. De Abreu, H.A., De Almeida, W.B., and Duarte, H.A., Chem. Phys. Lett., 2004, vol. 383, p. 47.
125. Delgado, E.J., Chem. Phys. Lett., 2009, vol. 471, p. 133.
126. Gibas, C.J. and Subramaniam, S., Biophys. J., 1996, vol. 71, p. 138.
127. Jang, Y.H., Hwang, S., and Chung, D.S., Chem. Lett., 2007, vol. 36, p. 1496.
128. Kamerlin, S.C.L., Haranczyk, M., and Warshel, A., J. Phys. Chem. B, 2009, vol. 113, p. 1253.
129. Khandogin, J. and Brooks, C.L., Biochemistry, 2006, vol. 45, p. 9363.
130. Kuhn, B., Kollman, P.A., and Stahl, M., J. Comput. Chem., 2004, vol. 25, p. 1865.
131. Lang, W. and Meier, N., Comput. Meth. Progr. Biomed., 2007, vol. 87, p. 160.
132. Li, H., Robertson, A.D., and Jensen, J.H., Proteins, 2005, vol. 61, p. 704.
133. Morgenthaler, M., Schweizer, E., Hoffmann-Roder, A., Benini, F., Martin, R.E., Jaeschke, G., Wagner, B., Fischer, H., Bendels, S., Zimmerli, D., Schneider, J., Diederich, F., Kansy, M., and Muller, K., ChemMedChem, 2007, vol. 2, p. 1100.
134. Nielsen, J.E. and McCammon, J.A., Protein Sci., 2003, vol. 12, p. 1894.
135. Nielsen, J.E. and McCammon, J.A., Protein Sci., 2003, vol. 12, p. 313.
136. Nielsen, J.E., Michael, L.J., and Ludwig, B., Meth. Enzymol., 2009, vol. 454, p. 233.
137. Ohno, K., Kamiya, N., Asakawa, N., Inoue, Y., and Sakurai, M., Chem. Phys. Lett., 2001, vol. 341, p. 387.
138. Ohno, K. and Sakurai, M., J. Comput. Chem., 2006, vol. 27, p. 906.
139. Click, T.H. and Kaminski, G.A., J. Phys. Chem. B, 2009, vol. 113, p. 7844.
140. He, Y., Xu, J., and Pan, X.M., Proteins, 2007, vol. 69, p. 75.
141. Tynan-Connolly, B.M. and Nielsen, J.E., Nucl. Acids Res., 2006, vol. 34, p. 48.
142. Wallace, J.A. and Shen J.K., Meth. Enzymol., 2009, vol. 466, p. 455.
143. Zhang, J.-D., Zhu, Q.-Z., Li, S.-J., and Tao, F.-M., Chem. Phys. Lett., 2009, vol. 475, p. 15.
144. Wang, X.X., Fu, H., Du, D.M., Zhou, Z.Y., Zhang, A.G., Su, C.F., and Ma, K.S., Chem. Phys. Lett., 2008, vol. 460, p. 339.
145. Zhou, Z.-Y., Jia, Z.-K., Du, D.-M., Zhang, A.-G., and Hou, R.-Y., Chem. Phys. Lett., 2007, vol. 439, p. 374.
146. Batistela, V.R., da Costa Cedran, J., Moisis de Oliveira, H.P., Scarminio, I.S., Ueno, L.T., Eduardo da Hora Machado, A., and Hioka, N., Dyes Pigm., 2010, vol. 86, p. 15.
147. Krul, M., Wrona, M., Page, C.S., and Bates, P.A., J. Chem. Theory Comput., 2006, vol. 2, p. 1520.
148. Alvarado-Gonzalez, M., Orrantia-Borunda, E., and Glossman-Mitnik, D., J. Mol. Struct. (Theochem), 2008, vol. 869, p. 105.
149. Fu, Y., Liu, L., Wang, Y.-M., Li, J.-N., Yu, T.-Q., and Guo, Q.-X., J. Phys. Chem. A, 2006, vol. 110, p. 5874.
150. Katritzky, A.R., Kuanar, M., Slavov, S., Hall, C.D., Karelson, M., Kahn, I., and Dobchev, D.A., Chem. Rev., 2010, vol. 110, p. 5714.
151. Carabias-Martinez, R., Rodriguez-Gonzalo, E., Dominguez-Alvarez, J., and Miranda-Cruz, E., Anal. Chim. Acta, 2007, vol. 584, p. 410.
152. Chaudry, U.A. and Popelier, P.L.A., J. Org. Chem., 2004, vol. 69, p. 233.
153. Esteki, M., Hemmateenejad, B., Khayamian, T., and Mohajeri, A., Chem. Biol. Drug Design, 2007, vol. 70, p. 413.
154. Gargallo, R., Sotriffer, C.A., Liedl, K.R., and Rode, B.M., J. Comput.-Aided Mol. Design, 1999, vol. 13, p. 611.
155. Ghasemi, J., Saaidpour, S., and Brown, S.D., J. Mol. Struct. (Theochem), 2007, vol. 805, p. 27.
156. Gieleciak, R. and Polanski, J., J. Chem. Inf. Model., 2007, vol. 47, p. 547.
157. Goudarzi, N. and Goodarzi, M., Mol. Phys., 2009, vol. 107, p. 1495.
158. Habibi-Yangjeh, A. and Danandeh-Jenagharad, M., Indian J. Chem., Sect. B, 2007, vol. 46, p. 478.
159. Habibi-Yangjeh, A., Danandeh-Jenagharad, M., and Nooshyar, M., Bull. Korean Chem. Soc., 2005, vol. 26, p. 2007.
160. Habibi-Yangjeh, A., Pourbasheer, E., and Danandeh-Jenagharad, M., Monatsh. Chem., 2009, vol. 140, p. 15.
161. Harding, A.P., Wedge, D.C., and Popelier, P.L.A., J. Chem. Inf. Model., 2009, vol. 49, p. 1914.
162. Jelfs, S., Ertl, P., and Selzer, P., J. Chem. Inf. Model., 2007, vol. 47, p. 450.
163. Jover, J., Bosque, R., and Sales, J., QSAR Comb. Sci., 2007, vol. 26, p. 385.
164. Jover, J., Bosque, R., and Sales, J., QSAR Comb. Sci., 2008, vol. 27, p. 1179.
165. Jover, J., Bosque, R., and Sales, J., QSAR Comb. Sci., 2008, vol. 27, p. 563.
166. Milletti, F., Storchi, L., Goracci, L., Bendels, S., Wagner, B., Kansy, M., and Cruciani, G., Eur. J. Med. Chem., 2010, vol. 45, p. 4270.
167. Milletti, F., Storchi, L., Sforna, G., and Cruciani, G., J. Chem. Inf. Model., 2007, vol. 47, p. 2172.
168. Polanski, J., Gieleciak, R., and Bamak, A., J. Chem. Inf. Comput. Sci., 2002, vol. 42, p. 184.
169. Roy, K. and Popelier, P.L.A., J. Phys. Org. Chem., 2009, vol. 22, p. 186.
170. Shan, X., Qin, W., Zhou, Z., and Dai, Y., J. Chem. Eng. Data, 2008, vol. 53, p. 331.
171. Tehan, B.G., Lloyd, E.J., Wong, M.G., Pitt, W.R., Manallack, D.T., and Gancia, E., Quant. Struct.-Act. Relat., 2002, vol. 21, p. 473.
172. Tehan, B.G., Lloyd, E.J., Wong, M.G., Pitt, W.R., Montana, J.G., Manallack, D.T., and Gancia, E., Quant. Struct.-Act. Relat., 2002, vol. 21, p. 457.
173. Xing, L. and Glen, R.C., J. Chem. Inf. Comput. Sci., 2002, vol. 42, p. 796.
174. Xing, L., Glen, R.C., and Clark, R.D., J. Chem. Inf. Comput. Sci., 2003, vol. 43, p. 870.
175. Zhang, J., Kleinoder, T., and Gasteiger, J., J. Chem. Inf. Model., 2006, vol. 46, p. 2256.
176. Brauner, N., Stateva, R.P., Cholakov, G.S., and Shacham, M., Abstracts of Papers, 16th European Symp. on Computer Aided Process Engineering and 9th Int. Symp. on Process Systems Engineering, Marquardt, W. and Pantelides, C., Eds., Amsterdam: Elsevier, 2006, p. 149.
177. Karelson, M., Lobanov, V.S., and Katritzky, A.R., Chem. Rev., 1996, vol. 96, p. 1027.
178. Katritzky, A.R., Fara, D.C., Petrukhin, R.O., Tatham, D.B., Maran, U., Lomaka, A., and Karelson, M., Curr. Top. Med. Chem., 2002, vol. 2, p. 1333.
179. Katritzky, A.R., Petrukhin, R., Tatham, D., Basak, S., Benfenati, E., Karelson, M., and Maran, U., J. Chem. Inf. Comput. Sci., 2001, vol. 41, p. 679.
180. Portal, C., Launay, D., Merritt, A., and Bradley, M., J. Comb. Chem., 2005, vol. 7, p. 554.
181. Braban, M., Pop, I., Willard, X., and Horvath, D., J. Chem. Inf. Comput. Sci., 1999, vol. 39, p. 1119.
182. Duchowicz, P.R., Talevi, A., Bruno-Blanch, L.E., and Castro, E.A., Bioorg. Med. Chem., 2008, vol. 16, p. 7944.
183. Ghafourian, T., Barzegar-Jalali, M., Dastmalchi, S., Khavari-Khorasani, T., Hakimiha, N., and Nokhodchi, A., Int. J. Pharm., 2006, vol. 319, p. 82.
184. Katritzky, A.R., Fara, D.C., Kuanar, M., Hur, E., and Karelson, M., J. Phys. Chem. A, 2005, vol. 109, p. 10 323.
185. Stairs, R.A. and Buncel, E., Can. J. Chem., 2006, vol. 84, p. 1580.
186. Toropov, A., Kudyshkin, V., Voropaeva, N., Ruban, I., and Rashidova, S., J. Struct. Chem., 2004, vol. 45, p. 945.
187. Ivanova, A.A., Baskin, I.I., Palyulin, V.A., and Zefirov, N.S., Dokl. Ross. Akad. Nauk, 2007, vol. 413, p. 766.
188. Khal'berstam, M.M., Baskin, I.I., Palyulin, V.A., and Zefirov, N.S., Dokl. Ross. Akad. Nauk, 2002, vol. 384, p. 202.
189. Kaneko, H., Arakawa, M., and Funatsu, K., J. Chem. Inf. Model., 2008, vol. 48, p. 534.
190. Gross, K.C., Seybold, P.G., Peralta-Inga, Z., Murray, J.S., and Politzer, P., J. Org. Chem., 2001, vol. 66, p. 6919.
191. Popelier, P.L.A. and Smith, P.J., Eur. J. Med. Chem., 2006, vol. 41, p. 862.
192. Bernazzani, L., Duce, C., Micheli, A., Mollica, V., Sperduti, A., Starita, A., and Tine, M.R., J. Chem. Inf. Model., 2006, vol. 46, p. 2030.
193. Bernazzani, L., Duce, C., Micheli, A., Mollica, V., and Tine, M.R., J. Chem. Eng. Data, 2010, vol. 55, p. 5425.
194. Abraham, M.H. and Acree, W.E., J. Org. Chem., 2010, vol. 75, p. 1006.
195. Zevatskii, Yu.E., Samoilov, D.V., and Mchedlov-Petrosyan, N.O., Russ. J. Gen. Chem., 2009, vol. 79, p. 1859.
196. Kamlet, M.J., Abboud, J.L.M., Abraham, M.H., and Taft, R.W., J. Org. Chem., 1983, vol. 48, p. 2877.
197. Parthasarathi, R., Padmanabhan, J., Elango, M., Chitra, K., Subramanian, V., and Chattaraj, P.K., J. Phys. Chem. A, 2006, vol. 110, p. 6540.
198. SPARC; http://sparc.chem.uga.edu/sparc/.
199. Oliferenko, A.A., Palyulin, V.A., Neiman, A.V., and Zefirov, N.S., Dokl. Chem., 2000, vol. 375, p. 281.
200. Shelley, J.C., Cholleti, A., Frye, L.L., Greenwood, J.R., Timlin, M.R., and Uchimaya, M., J. Comput.-Aided Mol. Design, 2007, vol. 21, p. 681.
201. Meloun, M. and Bordovska, S., Anal. Bioanal. Chem., 2007, vol. 389, p. 1267.
202. Dearden, J.C., Cronin, M.T.D., and Lappin, D.C., J. Pharm. Pharmacol., 2007, vol. 59, p. 7.
203. Liao, C. and Nicklaus, M.C., J. Chem. Inf. Model., 2009, vol. 49, p. 2801.
204. Balogh, G.T., Gyarmati, B., Nagy, B., Molnar, L., and Keseru, G.M., QSAR Comb. Sci., 2009, vol. 28, p. 1148.
205. SMILES; http://www.daylight.com/dayhtml-tutorials/languages/smiles/index. html.
206. Aschi, M., D'Archivio, A.A., Fontana, A., and Formiglio, A., J. Org. Chem., 2008, vol. 73, p. 3411.
207. Izutsu, K., Acid-Base Dissociation Constants in Dipolar Aprotic Solvents, Oxford: Blackwell Science, 1990.
208. Lee, A.C. and Crippen, G.M., J. Chem. Inf. Model., 2009, vol. 49, p. 2013.
209. Zevatskii, Yu.E. and Lysova, S.S., Russ. J. Org. Chem., 2009, vol. 45, p. 825.
210. Zevatskii, Yu.E. and Samoilov, D.V., Russ. J. Org. Chem., 2008, vol. 44, p. 1737.
211. Zevatskii, Yu.E. and Samoilov, D.V., Russ. J. Org. Chem., 2008, vol. 44, p. 52.
212. Zevatskii, Yu.E., Samoilov, D.V., and Panina, N.S., Russ. J. Gen. Chem., 2009, vol. 79, p. 944.
213. Milletti, F., Storchi, L., and Cruciani, G., Proteins, 2009, vol. 76, p. 484.
214. Milletti, F., Storchi, L., Sforna, G., Cross, S., and Cruciani, G., J. Chem. Inf. Model., 2009, vol. 49, p. 68.
215. Gross, K.C., Seybold, P.G., and Hadad, C.M., Int. J. Quantum Chem., 2002, vol. 90, p. 445.
216. Milletti, F., Storchi, L., and Cruciani, G., Proteins, 2009, vol. 76, p. 484.
217. Meloun, M., Bordovska, S., and Kupka, K., J. Math. Chem., 2010, vol. 47, p. 891.
218. Blanco, S.E., Almandoz, M.C., and Ferretti, F.H., Spectrochim. Acta, Part A, 2005, vol. 61, p. 93.