The n-octanol and n-hexane/water partition coefficient of environmentally relevant chemicals predicted from the mobile order and disorder (MOD) thermodynamics

Chemosphere

Volumn 40, Issue 5, 2000, Pages 457-512

  Ruelle, Paul ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

Hydrophobic effect; Mobile order and disorder theory; Partition; Pesticide; Thermodynamics

Indexed keywords

HEXANE; OCTANOL; ORGANIC COMPOUND; PESTICIDE; WATER;

AQUEOUS SOLUTION; ARTICLE; CHAOTIC DYNAMICS; HYDROPHOBICITY; LIPOPHILICITY; MISCIBILITY; MODEL; PARTITION COEFFICIENT; THERMODYNAMICS;

ENVIRONMENTAL POLLUTANTS; HEXANES; MODELS, CHEMICAL; PREDICTIVE VALUE OF TESTS; THERMODYNAMICS; WATER;

EID: 0033971341     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0045-6535(99)00268-4     Document Type: Article

References (132)

1. Abraham M.H., Chadha H.S., Whiting G.S., Mitchell R.C. J. Pharm. Sci. 83:1994;1085-1100.
2. Apelblat A. Ber. Bunsenges. Phys. Chem. 87:1983;2-5.
3. Basak S.C., Gute B.D., Grunwald G.D. J. Chem. Inf. Comput. Sci. 36:1996;1054-1060.
4. Berthelot, M., Jungfleisch, E., 1872. Ann. Chim. Phys. 4 (26), 396-407.
5. Birnbaum L.S. Environ. Health Perspect. 61:1985;11-20.
6. Bodor N., Buchwald P. J. Phys. Chem. B. 101:1997;3404-3412.
7. Bodor N., Gabanyi Z., Wong C.K. J. Amer. Chem. Soc. 111:1989;3783-3786.
8. Bodor N., Huang M.-J. J. Pharm. Sci. 81:1992;272-281.
9. Bowman B.T., Sans W.W. J. Environ. Sci. Health B. 18:1983;667-683.
10. Briggs G.G. J. Agric. Food Chem. 29:1981;1050-1059.
11. Buchwald P., Bodor N. Curr. Med. Chem. 5:1998;353-380.
12. Chen F., Holten-Andersen J., Tyle H. Chemosphere. 26:1993;1325-1354.
13. Chessells M., Hawker D.W., Connell D.W. Chemosphere. 22:1991;1175-1190.
14. Dai J., Jin L., Wang L., Zhang Z. Chemosphere. 37:1998;1419-1426.
15. Dallos A., Liszi J. J. Chem. Thermodyn. 27:1995;447-448.
16. Data file Pomona College, available from Biobyte Claremont, CA, USA.
17. de Bruijn J., Hermens J. Quant. Struct.-Act. Relat. 9:1990;11-21.
18. Devillers J., Bintein S., Domine D. Chemosphere. 33:1996;1047-1065.
19. de Voogt P., van Hattum B., Leonards P., Klamer J.C., Govers H.A.J. Aquatic Toxicol. 20:1991;169-194.
20. Doucette W.J., Andren A.W. Environ. Sci. Tech. 21:1987;821-824.
21. Dunn W.J., Koehler M.G., Grigoras S. J. Med. Chem. 30:1987;1121-1126.
22. Edward J.T. Can. J. Chem. 76:1998;1294-1303.
23. Edward J.T., Farrell P.G., Shahidi F. J. Chem. Soc. Faraday Trans. 73:1977;705-714.
24. Famini G.R., Penski C.A., Wilson L.Y. J. Phys. Org. Chem. 5:1992;395-408.
25. Famini G.R., Wilson L.Y. Chemosphere. 35:1997;2417-2447.
26. Finizio A., Sicbaldi F., Vighi M. SAR QSAR Environ. Res. 3:1995;71-80.
27. Finizio A., Vighi M., Sandroni D. Chemosphere. 34:1997;131-161.
28. Fischer R.G., Ballschmiter K. Chemosphere. 14:1988;2891-2901.
29. Flory, P.J., 1953. Principles of Polymer Chemistry. Cornell University Press, Ithaca, NY, 1953.
30. Fujita T., Nishioka T., Nakajima M. J. Med. Chem. 20:1977;1071-1081.
31. Garst J.E., Wilson W.C. J. Pharm. Sci. 73:1984;1616-1623.
32. Ghose A.K., Crippen G.M. J. Comput. Chem. 7:1986;565-577.
33. Gobas F.A.P.C., Lahittete J.M., Garofalo G., Shiu W.Y., Mackay D. J. Pharm. Sci. 77:1988;265-272.
34. Hansch C., Leo A. Substituent Constants for Correlation Analysis in Chemistry and Biology. 1979;Wiley, New York.
35. Hansch C., Leo A., Hoekman D. Exploring QSAR, Hydrophobic, Electronic, and Steric Constants. 1995;American Chemical Society, Washington, DC.
36. He Y.B., Wang L., Han S., Zhao Y., Zhang Z., Zou G. Chemosphere. 30:1995;117-125.
37. Huyskens P.L. J. Mol. Struct. 274:1992;223-246.
38. Huyskens P.L., Haulait-Pirson M.C. J. Mol. Liquids. 31:1985;135-151.
39. Huyskens P.L., Seghers K., Morissen H. Fluid Phase Equilibria. 96:1994;1-18.
40. Huyskens P.L., Siegel G.G. Bull. Soc. Chim. Belg. 97:1988;809-830.
41. Inel Y., Iseri R. Chemosphere. 35:1997;993-1002.
42. Iqbal M., Jamal M.A., Ahmed M., Ahmed B. Can. J. Chem. 72:1994;1076-1079.
43. Isnard P., Lambert S. Chemosphere. 18:1989;1837-1853.
44. Kamlet M.J., Abraham M.H., Doherty R.M., Taft R.W. J. Amer. Chem. Soc. 106:1984;464-466.
45. Kamlet M.J., Doherty R.M., Abraham M.H., Marcus Y., Taft R.W. J. Phys. Chem. 92:1988;5244-5255.
46. Kawamoto K., Urano K. Chemosphere. 18:1989;1987-1996.
47. Kleyle R.M., Nurok D., Kossoy A.D., Burris S.C. J. Chromatogr. A. 749:1996;211-217.
48. Klopman G., Li J.-Y., Wang S., Dimayuga M. J. Chem. Inf. Comput. Sci. 34:1994;752-781.
49. Klopman G., Namboodiri K., Schochet M. J. Comput. Chem. 6:1985;28-38.
50. Kurihara N., Yamakawa K., Fujita T., Nakajima M. J. Pesticide Sci. 5:1980;93-100.
51. Kurz J., Ballschmiter K. Chemosphere. 38:1999;573-586.
52. Leahy D.E. J. Pharm. Sci. 75:1986;629-636.
53. Leahy D.E., Morris J.J., Taylor P.J., Wait A.R. J. Chem. Soc. Prekin Trans. 2:1992;705-722.
54. Leahy D.E., Morris J.J., Taylor P.J., Wait A.R. J. Chem. Soc. Prekin Trans. 2:1992;723-731.
55. Leahy D.E., Morris J.J., Taylor P.J., Wait A.R. J. Phys. Org. Chem. 7:1994;743-750.
56. Leahy D.E., Taylor P.J., Wait A.R. Quant. Struct.-Act. Relat. 8:1989;17-31.
57. Leo A., Hansch C., Jow P.Y.C. J. Med. Chem. 19:1976;611-615.
58. Lewis D.F.V. J. Comput. Chem. 10:1989;145-151.
59. Li J., Perdue E.M., Pavlostathis S.G., Araujo R. Environ. Int. 24:1998;353-358.
60. Lun R., Shiu W.Y., Mackay D. J. Chem. Eng. Data. 40:1995;959-962.
61. Lun R., Varhanickova D., Shiu W.Y., Mackay D. J. Chem. Eng. Data. 42:1997;951-953.
62. Mackay, D., Shiu, W.Y., Ma, K.C., 1992a. Illustratred Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals, vol. 1, Monoaromatic Hydrocarbons, Chlorobenzenes, and PCBs. Lewis Publishers, Boca Raton, FL.
63. Mackay, D., Shiu, W.Y., Ma, K.C., 1992b. Illustratred Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals, vol. 2, Polynuclear Aromatic Hydrocarbons, Polychlorinated Dioxins, and Dibenzofurans. Lewis Publishers, Boca Raton, FL.
64. Mackay, D., Shiu, W.Y., Ma, K.C., 1993. Illustratred Handbook of Physical-Chemical Properties and Environmental Fate for organic Chemicals, vol. 3, Volatile Organic Chemicals. Lewis Publishers, Boca Raton, FL.
65. Mackay, D., Shiu, W.Y., Ma, K.C., 1997. Illustratred Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals, vol. 5, Pesticide Chemicals. Lewis Publishers, Boca Raton, FL.
66. Mailhot H., Peters R.H. Environ. Sci. Tech. 22:1988;1479-1488.
67. Makino M. Chemosphere. 37:1998;13-26.
68. Mannhold R., Cruciani G., Dross K., Rekker R. J. Comput.-Aided Mol. Design. 12:1998a;573-581.
69. Mannhold R., Rekker R.F., Dross K., Bijloo G., de Vries G. Quant. Struct.-Act. Relat. 17:1998b;517-536.
70. Marcus Y. J. Solution Chem. 19:1990;507-517.
71. Miller M.M., Wasik S.P., Huang G.L., Shiu W.Y., Mackay D. Environ. Sci. Tech. 19:1985;522-529.
72. Nakagawa Y., Izumi K., Oikawa N., Sotomatsu T., Shigemura M., Fujita T. Environ. Toxicol. Chem. 11:1992;901-916.
73. Nandihalli U.B., Duke M.V., Duke S.O. J. Agric. Food Chem. 41:1993;582-587.
74. Nernst W. Z. Phys. Chem. (Leipzig). 8:1891;110-139.
75. Noble A. J. Chromatogr. 642:1993;3-14.
76. Nouwen, J., Hansen, B., 1996. Quant. Struct.-Act. Relat. 15, 17-30.
77. Opperhuizen A., Van der Velde E.W., Gobas F.A.P.C., Kiem D.A.K., Van der Steen J.M.D., Hutzinger O. Chemosphere. 14:1985;1871-1896.
78. Paschke A., Popp P., Schüürmann G. Fresenius J. Anal. Chem. 363:1999;426-428.
79. Reddy K.N., Locke M.A. Water, Air and Soil Pollution. 86:1996;389-405.
80. Ruelle, P., 1999. Perspectives in Drug Discovery and Design, in press.
81. Ruelle P., Buchmann M., Hô N.-T., Kesselring U.W. Int. J. Pharm. 87:1992;47-57.
82. Ruelle P., Buchmann M., Hô N.-T., Kesselring U.W. J. Comput.-Aided Mol. Design. 6:1992;431-448.
83. Ruelle P., Buchmann M., Hô N.-T., Kesselring U.W. Environ. Sci. Tech. 27:1993;266-270.
84. Ruelle P., Buchmann M., Kesselring U.W. J. Pharm. Sci. 83:1994;396-403.
85. Ruelle P., Fariña-Cuendet A., Kesselring U.W. Int. J. Pharm. 157:1997;219-232.
86. Ruelle P., Kesselring U.W. Pharm. Res. 11:1994;201-205.
87. Ruelle P., Kesselring U.W. J. Solution Chem. 25:1996;657-665.
88. Ruelle P., Kesselring U.W. Chemosphere. 34:1997;275-298.
89. Ruelle P., Kesselring U.W. J. Chem. Soc. Faraday Trans. 93:1997;2049-2052.
90. Ruelle P., Kesselring U.W. J. Pharm. Sci. 86:1997;179-186.
91. Ruelle P., Kesselring U.W. Can. J. Chem. 76:1998;553-565.
92. Ruelle P., Kesselring U.W. J. Pharm. Sci. 87:1998;987-997.
93. Ruelle P., Kesselring U.W. J. Pharm. Sci. 87:1998;998-1014.
94. Ruelle P., Rey-Mermet C., Buchmann M., Hô N.-T., Kesselring U.W., Huyskens P.L. Pharm. Res. 8:1991;840-850.
95. Ruelle P., Sarraf E., Kesselring U.W. Int. J. Pharm. 104:1994;125-133.
96. Sabljic A. Sci. Total Environ. 109/110:1991;197-220.
97. Sabljic A., Güsten H., Verhaar H., Hermens J. Chemosphere. 31:1995;4489-4514.
98. Saçan M.T., Inel Y. Chemosphere. 30:1995;39-50.
99. Said A., Makki S., Muret P., Rouland J.-C., Toubin G., Millet J. J. Pharm. Sci. 85:1996;387-391.
100. Saito H., Koyasu J., Yoshida K., Shigeoka T., Koike S. Chemosphere. 26:1993;1015-1028.
101. Sangster J. LOGKOW - A Databank of Evaluated Octanol-Water Partition Coefficients. 1993;Sangster Research Laboratories, Montreal.
102. Sangster, J., 1997. Octanol-Water Partition Coefficients: Fundamentals and Physical Chemistry. Wiley, New York, pp. 113-156.
103. Sasaki Y., Kubodera H., Matuzaki T., Umeyama H. J. Pharmacobio-Dyn. 14:1991;207-214.
104. Schulte J., Dürr J., Ritter S., Hauthal W.H., Quittzsch K., Maurer G. J. Chem. Eng. Data. 43:1998;69-73.
105. Seiler P. Eur. J. Med. Chem. 9:1979;473-479.
106. Shahidi F., Farrell P.G., Edward J.T. J. Chem. Soc. Faraday Trans. 73:1977;715-721.
107. Sherblom P.M., Gschwend P.M., Eganhouse R.P. J. Chem. Eng. data. 37:1992;394-399.
108. Shiu W.Y., Doucette W.J., Gobas F.A.P.C., Andren A., Mackay D. Environ. Sci. Tech. 22:1988;651-658.
109. Shiu W.Y., Mackay D. J. Phys. Chem. Ref. Data. 15:1986;911-929.
110. Sicbaldi F., Del Re A.A.M. Reviews Environ. Contam. Toxicol. 133:1993;59-93.
111. Sijm D.H.T.M., Wever H., de Vries P.J., Opperhuizen A. Chemosphere. 19:1989;263-266.
112. Simpson C.D., Wilcock R.J., Smith T.J., Wilkins A.L., Langdon A.G. Bull. Environ. Contam. Toxicol. 55:1995;149-153.
113. Sixt S., Altschuh J., Brüggemann R. Chemosphere. 30:1995;2397-2414.
114. Smith R.N., Hansch C., Ames M.M. J. Pharm. Sci. 64:1975;599-606.
115. Suzuki T., Kudo Y. J. Comput.-Aided Mol. Design. 4:1990;155-198.
116. Takahashi J., Kirino O., Takayama C., Kamoshita K. J. Chromatogr. 436:1988;316-322.
117. Tam D., Varhanickova D., Shiu W.Y., Mackay D. J. Chem. Eng. Data. 39:1994;83-86.
118. Tanaka M., Horisaka K., Yamagami C., Takao N., Fujita T. Chem. Pharm. Bull. 33:1985;2403-2410.
119. Valsaraj K.T., Thibodeaux L.J. Separat. Sci. Tech. 25:1990;369-395.
120. van de Waterbeemd, H., Mannhold, R., 1996a. Lipophilicity descriptors for structure-property correlation studies: overview and experimental and theoretical methods and a benchmark of log P calculations. In: Pliška, V., Testa, B., van de Waterbeemd, H., (Eds.) Lipophilicity in Drug Action and Toxicology. Methods and Principles In Medicinal Chemistry, vol. 4. VCH Publishers, Weinheim, pp. 401-418.
121. van de Waterbeemd H., Mannhold R. Quant. Struct.-Act. Relat. 15:1996;410-412.
122. van Haelst A.G., Heesen P.F., van der Wielen F.W.M., Govers H.A.J. Chemosphere. 29:1994;1651-1660.
123. Van Krevelen, D.W., 1990. Properties of Polymers: Their Correlation with Chemical Structure; Their Numerical Estimation and Prediction from Additive Group Contributions, third ed. Elsevier, Amsterdam, pp. 212-213.
124. Wang R., Fu Y., Lai L. J. Chem. Inf. Comput. Sci. 37:1997;615-621.
125. Yalkowsky S.H., Valvani S.C. J. Med. Chem. 19:1976;727-728.
126. Yamagami C., Katashiba N. Chem. Pharm. Bull. 44:1996;1338-1343.
127. Yamagami C., Takami H., Yamamoto K., Myoshi K., Takao N. Chem. Pharm. Bull. 32:1984;4994-5002.
128. Yamagami C., Takao N. Chem. Pharm. Bull. 41:1993;694-698.
129. Yamagami C., Takao N., Tanaka M., Horisaka K., Fujita T. Chem. Pharm. Bull. 32:1984;5003-5009.
130. Yamagami C., Yamada J., Sonoda C., Takao N., Tanaka M., Horisaka K., Fujita T. Chem. Pharm. Bull. 30:1982;4175-4180.
131. Yamagami C., Masaki Y. Chem. Pharm. Bull. 43:1995;2238-2242.
132. Yoshida K., Shigeoka T., Yamauchi F. Ecotox. Environ. Safety. 7:1983;558-565.