Document Type : Original Research Article


1 Director of Ilam Petrochemical Company, Ilam, Iran

2 Department of Chemistry, Payame Noor University, P.O. BOX 19395-4697, Tehran, Iran


Aniline, phenol, and their derivatives are widely used in industrial chemicals that consequently have a high potential for environmental pollution. Genetic algorithm and partial least square (GA-PLS), kernel partial least square (GA-KPLS) and Levenberg-Marquardt artificial neural network (L-M ANN) techniques were used to investigate the correlation between chromatographic retention (log k) and descriptors for modelling the toxicity to fathead minnows of anilines and phenols. Descriptors of GA-PLS model were selected as inputs in L-M ANN model. The described model does not require experimental parameters and potentially provides useful prediction for log k of new compounds. Finally a model with a low prediction error and a good correlation coefficient was obtained by L-M ANN. The stability and prediction ability of L-M ANN model was validated using external test set techniques.

Graphical Abstract

Quantitative structure-retention relationships applied to chromatographic retention of ecotoxicity of anilines and phenols


Main Subjects

[1]. Sowers A.D., Gaworecki K.M., Mills M.A., Roberts A.P., Klaine S.J. Aquat. Toxicol., 2009, 95:173
[2]. Aruoja V., Sihtmäe M., Kahru A., Dubourguier H. Toxicol. Lett., 2009, 189:192
[3]. Al-Awadhi J.M., Al-Awadhi A.A. J. Arid Environ., 2009, 73:987
[4]. Duchowicz P.R., Giraudo M.A., Castro E.A., Pomilio A.B, Chemom. Intell. Lab. Syst., 2011, 107:384
[5]. Goodarzi M., Chen T., Freitas M.P. Chemom. Intell. Lab. Syst., 2010, 104:260
[6]. Liu T., Nicholls I.A., Oberg T., Anal. Chim. Acta., 2011, 702:37
[7]. Kaliszan R., Wiczling P., Markuszewski M.J., Al-Haj M.A. J. Chromatogr. A., 2011, 1218:5120
[8]. Flieger J. J. Chromatogr. A., 2010, 1217:540
[9]. Bucinski A., Wnuk M., Gorynski K., Giza A., Kochanczyk J., Nowaczyk A., Baczek T., Nasal A. JPharm Biomed Anal., 2009, 50:591
[10]. Lammerhofer M. J. Chromatogr. A., 2010, 1217:814
[11]. Shahpar M., Esmaeilpoor Sh. Asian J. Nano. Mat., 2018, 1:1
[12]. Ren S., Frymier P.D., Schultz T.W., Schultz, Ecotox. Environ. Safe, 2003, 55:86
[13]. Sarıpınar E., Geçen N., Şahin K., Yanmaz  E., Eur. J. Med. Chem., 2010, 45:4157
[14]. Sagrado S., Cronin M.T.D., Anal. Chim. Acta., 2008, 609:169
[15]. Hernández-Caraballo E.A., Rivas F., Pérez A.G., Marcó-Parra L.M. Anal. Chim. Acta., 2005, 533:161
[16]. Gupta V.K., Khani H., Ahmadi-Roudi B., Mirakhorli Sh., Fereyduni E., Agarwal Sh. Talanta, 2011, 83:1014
[17]. Bolanča T., Cerjan-Stefanović S., Regelja M., Regelja H., Lončarić S. J. Chromatogr. A, 2005, 1085:74
[18]. Chamjangali M.A., Beglari M., Bagherian G. J. Mol. Graphics Modell., 2007, 26:360
[19]. Shahpar M., Esmaeilpoor Sh. Asian J. Green Chem., 2017, 129:116
[20]. Jia R., Mao Zh., Chang Y., Zhang Sh, Chemom. Intell. Lab. Syst., 2010, 100:91
[21]. Jalali-Heravi M., Kyani A., Eur. J. Med. Chem., 2007, 42:649
[22]. Noorizadeh H., Noorizadeh M., Med Chem Res., 2013, 11:5442
[23]. Chen H., Anal. Chim. Acta., 2008, 609:24
[24]. Shahpar M., Esmaeilpoor Sh. Chem. Method., 2017, 2:105