Collection of Partition Coefficients in Hexadecyltrimethylammonium Bromide, Sodium Cholate, and Lithium Perfluorooctanesulfonate Micellar Solutions: Experimental Determination and Computational Predictions
Abstract
:1. Introduction
2. Results and Discussion
2.1. Experimental logP Values of SC, HTAB, and LPFOS Micelles
2.2. Correlation of logP Values in Micelles Using DFT Calculations
2.3. Estimation of logP Values in Micelles Using SVM Calculations
3. Materials and Methods
3.1. Regents and Materials
3.2. Determination of Partition Coefficients in Systems of SC, LPFOS, and HTAB Micelles
3.3. QM Computational Determination of Partition Coefficients
3.4. Correlation Analysis
3.5. Supervised and Unsupervised Methods
3.6. K-Means Clustering
3.7. Principal Component Analysis (PCA)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Micelle Name | Symbol | Structure | Schematic Representation of Formed Micelles |
---|---|---|---|
Hexadecyltrimethyl- ammonium bromide | HTAB | ||
Lithium perfluorooctanesulfonate | LPFOS | ||
Sodium cholate | SC |
Compound | logPSC | logPHTAB | logPLPFOS |
---|---|---|---|
Ethylbenzene | 2.50 | 3.00 | 2.06 |
Propylbenzene | 2.94 | 3.42 | 2.39 |
Butylbenzene | 3.26 | 3.71 | 2.71 |
1-Phenylethanone | 1.33 | 2.03 | 2.19 |
1-Phenylpropan-1-one | 1.65 | 2.42 | 2.44 |
1-Phenylbutan-1-one | 2.01 | 2.80 | 2.72 |
1-Phenylpentan-1-one | 2.41 | 3.24 | 3.01 |
1-Phenylheptan-1-one | 3.15 | - | 3.68 |
Furan | 0.77 | 1.48 | 1.19 |
2-Nitroaniline | 1.59 | 2.67 | 1.80 |
2,3-Benzofuran | 2.12 | 2.82 | 1.82 |
Diphenylmethanone | 2.48 | 3.28 | 3.01 |
Benzamide | 1.06 | 1.72 | 1.50 |
4-Chloroaniline | 1.69 | 2.69 | 1.44 |
2,3-Dimethylphenol | 1.90 | 3.15 | 1.66 |
Naphtalen-2-ol | 2.31 | - | 1.73 |
4-Aminobenzamide | 0.98 | 1.11 | 1.76 |
3-Methylphenol | 1.53 | 2.78 | 1.43 |
2,4-Dimethylphenol | 1.93 | 3.17 | 1.02 |
Naphthalene | 2.67 | 3.47 | 2.09 |
Pyrimidine | 0.56 | - | 1.27 |
Benzaldehyde | 1.20 | 1.91 | 1.91 |
3-Chloroaniline | 1.63 | 2.72 | 1.41 |
Pyrrole | 0.68 | 1.65 | 0.72 |
3-Nitroaniline | 1.38 | 2.42 | 1.53 |
4-Chlorophenol | 2.00 | 3.24 | 1.30 |
Phenol | 1.21 | 2.35 | 1.08 |
Methylbenzoate | 1.71 | 2.39 | 2.36 |
Bromobenzene | 2.37 | 2.95 | 1.80 |
1,4-Xylene | 2.51 | 3.04 | 2.10 |
Benzene-1,3-diol | 1.21 | 2.48 | 0.75 |
2-Methylaniline | 1.17 | 2.15 | 1.59 |
Aniline | 0.92 | 1.83 | 1.34 |
Nitrobenzene | 1.47 | 2.21 | 1.94 |
Chlorobenzene | 2.21 | 2.77 | 1.77 |
N-4-chlorophenylacetamide | 2.03 | 2.80 | 1.84 |
N-Phenylacetamide | 1.25 | 1.98 | 1.58 |
4-Nitroaniline | 1.52 | 2.50 | 1.45 |
Anisole | 1.66 | 2.31 | 1.83 |
Benzonitrile | 1.21 | 1.96 | 1.95 |
1-Ethyl-4-nitrobenzene | 2.19 | 3.02 | 2.68 |
Benzyl benzoate | 2.99 | - | 3.18 |
Caffeine | 1.11 | 1.32 | 1.85 |
Corticosterone | 1.94 | 3.69 | 3.64 |
Cortisone | 1.72 | 3.16 | 3.37 |
β-Estradiol | 2.77 | - | 2.84 |
Estriol | 2.32 | 3.52 | 2.01 |
Cortisol | 1.83 | 3.39 | 2.89 |
Hydroquinone | 1.09 | 1.94 | 0.19 |
Quinoline | 1.65 | 2.36 | 2.68 |
Atrazine | 1.86 | 1.90 | 2.71 |
Diuron | 2.46 | 2.19 | 2.34 |
Isoproturon | 2.19 | 1.95 | 2.61 |
Linuron | 2.59 | 2.24 | 2.50 |
Metobromuron | 2.16 | 2.03 | 2.22 |
Monuron | 1.81 | 1.73 | 2.03 |
Metoxuron | 1.69 | 1.46 | 2.34 |
Phenylurea | 1.20 | 1.20 | 1.38 |
Propazine | 2.02 | 2.08 | 3.03 |
Fluometuron | 2.01 | 1.92 | 2.57 |
N,N-Diethyl-4-nitroaniline | 2.44 | 3.56 | 3.36 |
1-Methoxy-4-nitrobenzene | 1.69 | 2.58 | 2.20 |
1-Methoxy-2-nitrobenzene | 1.55 | 2.37 | 2.26 |
Micelle | Solvent | B3LYP |
---|---|---|
LPFOS | Propan-1-ol | y = 0.46x + 0.77 R2 = 0.52 MAE = 0.87 |
Propan-2-ol | y = 0.49x + 0.61 R2 = 0.53 MAE = 0.92 | |
Methanol | y = 0.41x + 0.90 R2 = 0.43 MAE = 0.86 | |
SC | Propan-1-ol | y = 0.47x + 0.55 R2 = 0.67 MAE = 0.92 |
Propan-2-ol | y = 0.46x + 0.51 R2 = 0.64 MAE = 1.08 | |
Methanol | y = 0.41x + 0.68 R2 = 0.58 MAE = 0.89 | |
HTAB | Propan-1-ol | y = 0.23x + 1.80 R2 = 0.13 MAE = 0.74 |
Propan-2-ol | y = 0.22x + 1.83 R2 = 0.1 MAE = 0.72 | |
Methanol | y = 0.24x + 1.78 R2 = 0.13 MAE = 0.72 | |
HTAB without N set * | Propan-1-ol | y = 0.56x + 1.24 R2 = 0.66 MAE = 0.45 |
Propan-2-ol | y = 0.54x + 1.24 R2 = 0.62 MAE = 0.43 | |
Methanol | y = 0.56x + 1.26 R2 = 0.63 MAE = 0.46 |
SC | HTAB | LPFOS | |
---|---|---|---|
Variables (descriptors) | Mv, RBN, RBF, H%, N%, O%, NRS, nR09, nR10, X4Av, P_VSA_LogP_2, P_VSA_s_4, P_VSA_ppp_P, P_VSA_charge_1, P_VSA_charge_3, P_VSA_charge_4, P_VSA_charge_5, P_VSA_charge_13, P_VSA_charge_14 | nSK, nH, N%, Xu, S1K, DELS, BAC, X0, X0sol, P_VSA_LogP_1, P_VSA_LogP_4, P_VSA_LogP_6, P_VSA_LogP_8, P_VSA_MR_5, P_VSA_m_5, P_VSA_s_3, P_VSA_ppp_D, P_VSA_charge_2, P_VSA_charge_4, P_VSA_charge_5, P_VSA_charge_6, P_VSA_charge_9, P_VSA_charge_12, P_VSA_charge_14, qpmax, qnmax, Qpos, Qneg, Qtot, Qmean, Q2, RPCG, RNCG, TPSA(NO), TPSA(Tot) | RBF, nTB, MaxTD, P_VSA_LogP_2, P_VSA_LogP_3, P_VSA_LogP_4, P_VSA_MR_2, P_VSA_s_3, P_VSA_charge_2, P_VSA_charge_6, P_VSA_charge_7, P_VSA_charge_9, P_VSA_charge_13, P_VSA_charge_14, Qmean |
R2 | 0.693 | 0.565 | 0.783 |
RMSE | 0.369 | 0.248 | 0.202 |
MAE | 0.318 | 0.241 | 0.304 |
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Saranjam, L.; Nedyalkova, M.; Fuguet, E.; Simeonov, V.; Mas, F.; Madurga, S. Collection of Partition Coefficients in Hexadecyltrimethylammonium Bromide, Sodium Cholate, and Lithium Perfluorooctanesulfonate Micellar Solutions: Experimental Determination and Computational Predictions. Molecules 2023, 28, 5729. https://doi.org/10.3390/molecules28155729
Saranjam L, Nedyalkova M, Fuguet E, Simeonov V, Mas F, Madurga S. Collection of Partition Coefficients in Hexadecyltrimethylammonium Bromide, Sodium Cholate, and Lithium Perfluorooctanesulfonate Micellar Solutions: Experimental Determination and Computational Predictions. Molecules. 2023; 28(15):5729. https://doi.org/10.3390/molecules28155729
Chicago/Turabian StyleSaranjam, Leila, Miroslava Nedyalkova, Elisabet Fuguet, Vasil Simeonov, Francesc Mas, and Sergio Madurga. 2023. "Collection of Partition Coefficients in Hexadecyltrimethylammonium Bromide, Sodium Cholate, and Lithium Perfluorooctanesulfonate Micellar Solutions: Experimental Determination and Computational Predictions" Molecules 28, no. 15: 5729. https://doi.org/10.3390/molecules28155729