A Computational Route to Hansen Solubility Parameters of Nitrated (Chapter 3)

QSAR Correlation with Literature Values Figures 7 through 15 illustrate the correlation of the various transformation matrices to the literature values used in each training set. The R-squared values shown are not a direct measure of the predictive power of the model. They only indicate the consistency of the model with the training set values. The equation of the trendline is included to show the slope of the trendline and not to indicate any correlation to some variable “x.” QSAR1 D‐Parameter 25 y = 0.5026x + 8.5128 R² = 0.4737 Calculated  / MPa1/2 20 15 10 5 0 0 5 10 15 20 25 Literature  / MPa1/2 Figure 7. Correlation of QSAR1 predicted D parameters of training set species to literature values. QSAR1 P‐Parameter 20 y = 0.6383x + 2.2011 R² = 0.6472 Calculated  / MPa1/2 15 10 5 0 0 5 10 ‐5 15 20 25 30 Literature  / MPa1/2 Figure 8. Correlation of QSAR1 predicted P parameters of training set species to literature values. QSAR1 H‐Parameter 40 35 y = 0.7571x + 1.8564 R² = 0.7594 Calculated  / MPa1/2 30 25 20 15 10 5 0 ‐5 0 ‐10 5 10 15 20 25 30 35 40 45 Literature  / MPa1/2 Figure 9. Correlation of QSAR1 predicted H parameters of training set species to literature values. QSAR2 D‐Parameter 25 y = 0.5659x + 7.2454 R² = 0.5806 Calculated  / MPa1/2 20 15 10 5 0 0 5 10 15 20 25 Liturature  / MPa1/2 Figure 10. Correlation of QSAR2 predicted D parameters of training set species to literature values. QSAR2 P‐Parameter 25 y = 0.7446x + 1.6093 R² = 0.7381 Calculated  / MPa1/2 20 15 10 5 0 0 5 10 15 20 25 30 ‐5 Liturature  / MPa1/2 Figure 11. Correlation of QSAR2 predicted P parameters of training set species to literature values. QSAR2 H‐Parameter 45 40 y = 0.9023x + 0.9352 R² = 0.8771 Calculated  / MPa1/2 35 30 25 20 15 10 5 0 ‐5 0 5 10 15 20 25 30 35 40 45 Liturature  / MPa1/2 Figure 12. Correlation of QSAR2 predicted H parameters of training set species to literature values. QSAR3 D‐Parameter 25 Calculated  / MPa1/2 y = 0.813x + 3.3321 R² = 0.8132 20 15 10 5 0 0 5 10 15 20 25 Literature  / MPa1/2 Figure 13. Correlation of QSAR3 predicted D parameters of training set species to literature values. QSAR3 P‐Parameter 25 y = 0.9026x + 0.9559 R² = 0.9008 Calculated  / MPa1/2 20 15 10 5 0 0 5 10 ‐5 15 20 25 Literature  / MPa1/2 Figure 14. Correlation of QSAR3 predicted P parameters of training set species to literature values. QSAR3 H‐Parameter 45 Calculated  / MPa1/2 40 y = 0.8868x + 1.0192 R² = 0.887 35 30 25 20 15 10 5 0 0 5 10 15 20 25 30 35 40 45 Literature  / MPa1/2 Figure 15. Correlation of QSAR3 predicted H parameters of training set species to literature values. Predicted HSPs of Nitrated Unknowns Tables 4 through 6 display the predicted Hansen solubility parameters of the nitrated species of interest. Table 4. HSPs of Explosive Unknowns Predicted by QSAR1. Abbreviated Name HNS HNAB TACOT TNC tetryl ethyltetryl picric acid picramide TATB DATB TNB TNCB TNR TNBA TNA TNX PETN HMX RDX phloroglucinol TNPG TETNB ethylpicrate Explosive Unknowns IUPAC Nomenclature (E)1,3,5-Trinitro-2-[2-(2,4,6trinitrophenyl)ethenyl]benzene 2,2',4,4',6,6'-hexanitroazobenzene tetranitrodibenzo-1,3a,4,6a-tetrazapentalene 1,3,6,8-tetranitrocarbazole 2,4,6-trinitrophenylmethylnitramine 2,4,6-trinitrophenylethylnitramine 2,4,6-trinitrophenol 1,3,5-trinitroaniline 1,3,5-triamino-2,4,6-trinitrobenzene 1,3-diamino-2,4,6-trinitrobenzene 1,3,5-trinitrobenzene 2,4,6-trinitrochlorobenzene 3-hydroxyl-2,4,6-trinitrophenol 2,4,6-trinitrobenzoic acid 2,4,6-trinitroanisole 3-methyl-2,4,6-trinitrotoluene 3-nitrooxy-2,2-bis(nitrooxymethyl)propyl nitrate 1,3,5,7-tetranitro-1,3,5,7-tetrazocane 1,3,5-trinitro-1,3,5-triazinane benzene-1,3,5-triol 2,4,6-trinitrobenzene-1,3,5-triol 2,4,6-trinitro-1,3,5-triethoxybenzene 2,4,6-trinitroethoxybenzene Calculated HSPs D P H 30.2 7.3 8.7 32.0 27.7 28.3 23.1 22.9 21.6 22.7 24.2 23.9 21.4 21.6 21.9 21.4 21.7 21.3 19.9 6.1 16.3 8.1 11.4 14.0 9.2 13.7 6.9 12.8 3.7 3.8 9.1 7.1 9.4 6.7 3.6 10.5 8.1 22.4 8.3 8.0 16.6 21.5 22.0 21.8 8.0 7.6 17.1 14.3 9.4 6.7 6.3 21.7 20.4 17.8 22.3 21.5 21.8 12.6 10.6 10.3 11.3 4.9 10.1 8.2 8.8 15.5 17.1 6.5 9.3 Table 5. HSPs of Explosive Unknowns Predicted by QSAR2. Abbreviated Name HNS HNAB TACOT TNC tetryl ethyltetryl picric acid picramide TATB DATB TNB TNCB TNR TNBA TNA TNX PETN HMX RDX phloroglucinol TNPG TETNB ethylpicrate Explosive Unknowns IUPAC Nomenclature (E)1,3,5-Trinitro-2-[2-(2,4,6trinitrophenyl)ethenyl]benzene 2,2',4,4',6,6'-hexanitroazobenzene tetranitrodibenzo-1,3a,4,6a-tetrazapentalene 1,3,6,8-tetranitrocarbazole 2,4,6-trinitrophenylmethylnitramine 2,4,6-trinitrophenylethylnitramine 2,4,6-trinitrophenol 1,3,5-trinitroaniline 1,3,5-triamino-2,4,6-trinitrobenzene 1,3-diamino-2,4,6-trinitrobenzene 1,3,5-trinitrobenzene 2,4,6-trinitrochlorobenzene 3-hydroxyl-2,4,6-trinitrophenol 2,4,6-trinitrobenzoic acid 2,4,6-trinitroanisole 3-methyl-2,4,6-trinitrotoluene 3-nitrooxy-2,2-bis(nitrooxymethyl)propyl nitrate 1,3,5,7-tetranitro-1,3,5,7-tetrazocane 1,3,5-trinitro-1,3,5-triazinane benzene-1,3,5-triol 2,4,6-trinitrobenzene-1,3,5-triol 2,4,6-trinitro-1,3,5-triethoxybenzene 2,4,6-trinitroethoxybenzene Calculated HSPs D P H 30.2 13.8 9.0 30.9 29.3 32.2 23.2 23.8 22.3 26.4 27.7 27.2 21.3 21.7 22.7 21.6 21.5 21.3 20.3 15.2 14.7 13.0 11.3 12.6 10.0 11.6 9.6 10.8 8.8 8.5 9.7 9.4 10.3 8.3 8.0 9.7 7.5 15.1 6.5 6.5 13.4 17.3 16.9 17.1 5.9 5.9 13.8 11.2 7.1 5.7 5.2 22.1 20.0 18.4 23.1 20.8 21.8 11.0 9.7 8.7 10.7 7.7 10.8 6.2 6.5 15.0 13.7 6.3 7.1 Table 6. HSPs of Explosive Unknowns Predicted by QSAR3. Abbreviated Name HNS HNAB TACOT TNC tetryl ethyltetryl picric acid picramide TATB DATB TNB TNCB TNR TNBA TNA TNX PETN HMX RDX phloroglucinol TNPG TETNB ethylpicrate Explosive Unknowns IUPAC Nomenclature (E)1,3,5-Trinitro-2-[2-(2,4,6trinitrophenyl)ethenyl]benzene 2,2',4,4',6,6'-hexanitroazobenzene tetranitrodibenzo-1,3a,4,6a-tetrazapentalene 1,3,6,8-tetranitrocarbazole 2,4,6-trinitrophenylmethylnitramine 2,4,6-trinitrophenylethylnitramine 2,4,6-trinitrophenol 1,3,5-trinitroaniline 1,3,5-triamino-2,4,6-trinitrobenzene 1,3-diamino-2,4,6-trinitrobenzene 1,3,5-trinitrobenzene 2,4,6-trinitrochlorobenzene 3-hydroxyl-2,4,6-trinitrophenol 2,4,6-trinitrobenzoic acid 2,4,6-trinitroanisole 3-methyl-2,4,6-trinitrotoluene 3-nitrooxy-2,2-bis(nitrooxymethyl)propyl nitrate 1,3,5,7-tetranitro-1,3,5,7-tetrazocane 1,3,5-trinitro-1,3,5-triazinane benzene-1,3,5-triol 2,4,6-trinitrobenzene-1,3,5-triol 2,4,6-trinitro-1,3,5-triethoxybenzene 2,4,6-trinitroethoxybenzene Calculated HSPs D P H 20.7 17.1 5.6 23.0 20.3 20.9 18.5 18.9 18.9 19.2 18.5 18.8 19.1 19.5 19.3 19.0 18.8 18.1 16.8 22.0 13.4 14.8 13.2 14.6 12.5 13.8 13.4 12.6 10.8 11.4 14.0 13.0 11.7 8.7 17.8 6.5 3.4 21.0 5.6 5.4 15.4 19.4 21.1 19.7 6.7 6.5 15.9 13.7 7.6 5.7 6.4 15.3 15.5 19.7 19.9 17.8 18.7 13.4 11.1 11.9 16.6 12.9 11.6 5.6 6.5 15.5 15.4 8.2 7.8