Table S 12
Relevant quantities of the calculated conformers of the molecular structures utilized to investigate the influence ofspecific structural features of hyperjovinol A on the formation of complexes with Cu2+.
DFT/B3LYP/6-31+G(d,p) results.The results in vacuo are from full-optimization calculations. The results in solution are from single point PCM calculations performed on the in-vacuo optimized geometry.
The table considers the structures B, D, E, F, G, PHG1 and PHG, and the conformers corresponding to those yielding the best complexes between hyperjovinol A and a Cu2+ ion. The nature of these structures is shown in figure 5.
For each structure, the table reports (in separate pages):
- a comparison of the conformers’ relative energies in different media
- a comparison of the conformers’ dipole moment in different media
- the values of the solvent effect, Gsolv, and its electrostatic component, Gel (thermodynamic quantities of the solution process) in chloroform, acetonitrile and water.
Structure B
Structure B:comparison of the relative energy in different media
conformer / relative energy (kcal/mol)in vacuo / in chloroform / in acetonitrile / in water
d-r-q2 / 0.0000 / 0.0000 / 0.0000 / 0.0000
s-w-q1 / 2.8927 / 2.1491 / 1.8158 / 1.3358
d-w-f2 / 8.2157 / 6.6811 / 5.8713 / 3.2063
d-r-f1 / 10.1133 / 9.5657 / 9.0777 / 7.8397
d-w-f1 / 10.4498 / 8.4942 / 7.2763 / 4.6164
Structure B:comparison of the dipole moment in different media
conformer / dipole moment (debye)in vacuo / in chloroform / in acetonitrile / in water
d-r-q2 / 3.2263 / 3.7814 / 4.0762 / 4.4874
s-w-q1 / 7.0806 / 8.1636 / 8.5745 / 9.0586
d-w-f2 / 4.0727 / 5.1273 / 5.5921 / 6.3171
d-r-f1 / 4.0448 / 4.9969 / 5.5238 / 6.3072
d-w-f1 / 5.9278 / 7.4939 / 8.2875 / 9.3335
Structure B:thermodynamic quantities of the solution process
conformer / Gsolv (kcal/mol) / Gel (kcal/mol)in chloroform / in acetonitrile / in water / in chloroform / in acetonitrile / in water
d-r-q2 / -0.79 / 5.01 / -8.44 / -4.71 / -6.72 / -16.05
s-w-q1 / -1.16 / 4.29 / -9.54 / -5.46 / -7.80 / -17.60
d-w-f2 / -1.83 / 3.17 / -12.85 / -6.25 / -9.07 / -21.06
d-r-f1 / -0.47 / 4.73 / -9.87 / -5.26 / -7.76 / -18.32
d-w-f1 / -2.00 / 2.50 / -13.51 / -6.67 / -9.90 / -21.88
Structure D
Structure D:comparison of relative energy in different media
conformer / relative energy (kcal/mol)in vacuo / in chloroform / in acetonitrile / in water
d-r-q2 / 0.0000 / 0.0000 / 0.0000 / 0.0000
s-w-q1 / 0.9616 / 0.8810 / 0.8475 / 0.5973
d-r-f1 / 5.6794 / 5.5282 / 5.2676 / 4.0038
d-w-f2 / 6.5332 / 4.9207 / 3.9041 / 1.1940
d-w-f1 / 6.8464 / 5.1037 / 4.1075 / 1.1027
Structure D:comparison of the dipole moment in different media
conformer / dipole moment (debye)in vacuo / in chloroform / in acetonitrile / in water
d-r-q2 / 5.5190 / 6.1509 / 6.4134 / 6.7340
s-w-q1 / 7.7627 / 8.8025 / 9.1555 / 9.4655
d-r-f1 / 2.8452 / 3.5347 / 3.8967 / 4.4670
d-w-f2 / 5.3644 / 6.6681 / 7.2863 / 8.1334
d-w-f1 / 4.8503 / 6.1020 / 6.6775 / 7.4758
Structure D:thermodynamic quantities of the solution process
conformer / Gsolv (kcal/mol) / Gel (kcal/mol)in chloroform / in acetonitrile / in water / in chloroform / in acetonitrile / in water
d-r-q2 / 0.02 / 5.84 / -6.65 / -4.46 / -6.32 / -14.82
s-w-q1 / 0.53 / 6.17 / -6.49 / -4.54 / -6.44 / -15.18
d-r-f-1 / 0.32 / 5.91 / -7.80 / -4.62 / -6.73 / -16.49
d-w-f-2 / -1.34 / 3.55 / -11.59 / -6.08 / -8.95 / -20.15
d-w-f-1 / -1.38 / 3.51 / -11.92 / -6.21 / -9.06 / -20.56
Structure E
Structure E:comparison of the relative energy in different media
conformer / relative energy (kcal/mol)in vacuo / in chloroform / in acetonitrile / in water
d-r-q2 / 0.0000 / 0.0000 / 0.0000 / 0.0000
s-w-q1 / 0.9521 / 0.7402 / 0.6208 / 0.5072
d-r-f1 / 5.2214 / 5.0779 / 4.8158 / 3.6022
d-w-f2 / 5.7312 / 4.3575 / 3.4389 / 0.8360
d-w-f1 / 6.3829 / 4.6768 / 3.5734 / 0.9964
Structure E:comparison of the dipole moment in different media
conformer / dipole moment (debye)in vacuo / in chloroform / in acetonitrile / in water
d-r-q2 / 4.6499 / 5.2124 / 5.4356 / 5.6939
s-w-q1 / 7.5110 / 8.5853 / 8.9787 / 9.3867
d-w-f2 / 4.2980 / 5.3860 / 5.8552 / 6.5825
d-r-f1 / 4.0539 / 4.9930 / 5.5057 / 6.2131
d-w-f1 / 6.0660 / 7.5903 / 8.3312 / 9.3106
Structure E:thermodynamic quantities of the solution process
conformer / Gsolv (kcal/mol) / Gel (kcal/mol)in chloroform / in acetonitrile / in water / in chloroform / in acetonitrile / in water
d-r-q2 / -0.63 / 5.29 / -7.42 / -4.85 / -6.79 / -15.51
s-w-q1 / -0.29 / 5.40 / -7.31 / -5.06 / -7.12 / -15.95
d-w-f2 / -1.60 / 3.43 / -11.83 / -6.23 / -9.08 / -20.40
d-r-f1 / -0.29 / 5.36 / -8.54 / -5.00 / -7.20 / -17.13
d-w-f1 / -1.96 / 2.89 / -12.35 / -6.56 / -9.60 / -20.90
Structure F
Structure F:comparison of the relative energy in different media
conformer / relative energy (kcal/mol)in vacuo / in chloroform / in acetonitrile / in water
d-r-q2 / 0.0000 / 0.0000 / 0.0000 / 0.0000
s-w-q1 / 0.9975 / 0.7210 / 0.6789 / 0.5894
d-r-f1 / 5.2266 / 5.0996 / 4.8871 / 3.6392
d-w-f2 / 5.6929 / 4.2818 / 3.4416 / 0.8174
d-w-f1 / 6.3100 / 4.6198 / 3.6120 / 0.9340
Structure F:comparison of the dipole moment in different media
conformer / dipole moment (debye)in vacuo / in chloroform / in acetonitrile / in water
d-r-q2 / 4.6032 / 5.1914 / 5.4249 / 5.7080
s-w-q1 / 7.4358 / 8.5767 / 8.9853 / 9.4310
d-w-f2 / 4.2536 / 5.3373 / 5.8150 / 6.5291
d-r-f1 / 4.1380 / 5.0967 / 5.5921 / 6.3257
d-w-f1 / 6.1597 / 7.6989 / 8.4331 / 9.4208
Structure F:thermodynamic quantities of the solution process
conformer / Gsolv (kcal/mol) / Gel (kcal/mol)in chloroform / in acetonitrile / in water / in chloroform / in acetonitrile / in water
d-r-q2 / -1.83 / 2.69 / -9.31 / -4.77 / -6.74 / -15.28
s-w-q1 / 2.77 / -1.61 / -9.22 / -5.04 / -7.06 / -15.69
d-w-f2 / -2.90 / 0.82 / -13.75 / -6.18 / -8.99 / -20.16
d-r-f1 / -1.53 / 2.79 / -10.44 / -4.89 / -7.08 / -16.87
d-w-f1 / -3.19 / 0.36 / -14.27 / -6.46 / -9.44 / -20.66
Structure G
Structure G:comparison of the relative energy in different media
conformer / relative energy (kcal/mol)in vacuo / in chloroform / in acetonitrile / in water
d-r-q2 / 0.0000 / 0.0000 / 0.0000 / 0.0000
s-w-q1 / 0.8756 / 0.5941 / 0.5434 / 0.4707
d-r-f1 / 5.2430 / 5.2068 / 4.9950 / 3.6888
d-w-f1 / 6.3237 / 4.7181 / 3.7192 / 1.0087
d-w-f2 / 6.6119 / 5.6484 / 5.0103 / 3.6017
Structure G:comparison of the dipole moment in different media
conformer / dipole moment (debye)in vacuo / in chloroform / in acetonitrile / in water
d-r-q2 / 4.9269 / 5.5466 / 5.7982 / 6.0576
s-w-q1 / 8.0023 / 9.1308 / 9.5241 / 9.9440
d-r-f1 / 4.5744 / 5.5761 / 6.0890 / 6.7786
d-w-f- / 6.5069 / 8.0769 / 8.8103 / 9.7619
d-w-f2 / 5.2411 / 6.4588 / 6.9478 / 7.7260
Structure G:thermodynamic quantities of the solution process
conformer / Gsolv (kcal/mol) / Gel (kcal/mol)in chloroform / in acetonitrile / in water / in chloroform / in acetonitrile / in water
d-r-q2 / -2.66 / 2.24 / -11.63 / -5.50 / -7.75 / -17.72
s-w-q1 / -2.73 / 2.08 / -11.83 / -5.78 / -8.08 / -18.13
d-r-f1 / -2.23 / 2.47 / -12.70 / -5.53 / -8.00 / -19.28
d-w-f1 / -3.90 / 0.05 / -16.49 / -7.10 / -10.36 / -23.04
d-w-f2 / -2.99 / 1.24 / -13.90 / -6.46 / -9.35 / -20.73
Structure PHG1
Structure PHG1:comparison of the relative energy in different media
conformer / relative energy (kcal/mol)in vacuo / in chloroform / in acetonitrile / in water
d-r / 0.0000 / 0.1188 / 0.7204 / 1.8714
s-w / 0.6220 / 0.5756 / 1.0450 / 2.4686
d-w / 1.1314 / 0.0000 / 0.0000 / 0.0000
Structure PHG1:comparison of the dipole moment in different media
conformer / dipole moment (debye)in vacuo / in chloroform / in acetonitrile / in water
d-r / 3.4265 / 4.2610 / 4.6362 / 5.2225
s-w / 4.2744 / 5.1728 / 5.5262 / 5.9882
d-w / 5.7156 / 7.0686 / 7.6638 / 8.5415
structure PHG1:thermodynamic quantities of the solution process
conformer / Gsolv (kcal/mol) / Gel (kcal/mol)in chloroform / in acetonitrile / in water / in chloroform / in acetonitrile / in water
d-r / -2.30 / 0.62 / -8.96 / -3.87 / -5.53 / -12.39
s-w / -2.44 / 0.33 / -8.97 / -4.04 / -5.83 / -12.42
d-w / -3.59 / -1.25 / -11.94 / -5.12 / -7.38 / -15.39
Structure PHG (phloroglucinol)
Structure PHG:comparison of relative energy in different media
conformer / relative energy (kcal/mol)in vacuo / in chloroform / in acetonitrile / in water
PHG-1 / 0.0000 / 0.0000 / 0.0000 / 0.0000
PHG-2 / 0.8020 / 0.5253 / 0.1322 / 0.0770
Structure PHG:comparison of the dipole moment in different media
conformer / dipole moment (debye)in vacuo / in chloroform / in acetonitrile / in water
PHG-1 / 0.0012 / 0.0012 / 0.0013 / 0.0031
PHG-2 / 2.7678 / 3.3351 / 3.5977 / 3.9748
Structure PHG:thermodynamic quantities of the solution process
conformer / Gsolv (kcal/mol) / Gel (kcal/mol)in chloroform / in acetonitrile / in water / in chloroform / in acetonitrile / in water
PHG-1 / -5.65 / -5.23 / -16.93 / -5.92 / -8.42 / -18.35
PHG-2 / -5.92 / -5.90 / -17.65 / -6.19 / -9.09 / -19.08