Comparison Across Structures of the Relative Energies of Corresponding Conformers Of

Table S 13

Comparison across structures of the relative energies of corresponding conformers of hyperjovinol A and of other structures calculated to investigate the influence ofspecific features 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 each structure is shown in figure 5.

a) Comparison of conformers’ relative energies in vacuo

conformer / relative energy (kcal/mol)
HPJ-A / B / D / E / F / G
d-r-q2 / 0.0000 / 0.0000 / 0.0000 / 0.0000 / 0.0000 / 0.0000
s-w-q1 / 0.9613 / 2.8927 / 0.9616 / 0.9521 / 0.9975 / 0.8756
d-r-f1 / 3.8266 / 10.1133 / 5.6794 / 5.2214 / 5.2266 / 5.2430
d-w-f2 / 5.7231 / 8.2157 / 6.5332 / 5.7312 / 5.6929 / 6.6119
d-w-f1 / 6.3698 / 10.4498 / 6.8464 / 6.3829 / 6.3100 / 6.3237

b) Comparison of conformers’ relative energies in chloroform solution

conformer / relative energy (kcal/mol)
HPJ-A / B / D / E / F / G
d-r-q2 / 0.0000 / 0.0000 / 0.0000 / 0.0000 / 0.0000 / 0.0000
s-w-q1 / 0.8109 / 2.1491 / 0.8810 / 0.7402 / 0.7210 / 0.5941
d-r-f1 / 5.1576 / 9.5657 / 5.5282 / 5.0779 / 5.0996 / 5.2068
d-w-f2 / 4.3392 / 6.6811 / 4.9207 / 4.3575 / 4.2818 / 5.6484
d-w-f1 / 4.7222 / 8.4942 / 5.1037 / 4.6768 / 4.6198 / 4.7181

c) Comparison of conformers’ relative energies in acetonitrile solution

conformer / relative energy (kcal/mol)
HPJ-A / B / D / E / F / G
d-r-q2 / 0.0000 / 0.0000 / 0.0000 / 0.0000 / 0.0000 / 0.0000
s-w-q1 / 0.7888 / 1.8158 / 0.8475 / 0.6208 / 0.6789 / 0.5434
d-r-f1 / 4.9249 / 9.0777 / 5.2676 / 4.8158 / 4.8871 / 4.9950
d-w-f2 / 3.6589 / 5.8713 / 3.9041 / 3.4389 / 3.4416 / 5.0103
d-w-f1 / 3.7474 / 7.2763 / 4.1075 / 3.5734 / 3.6120 / 3.7192

d) Comparison of conformers’relative energies in water solution

conformer / relative energy (kcal/mol)
HPJ-A / B / D / E / F / G
d-r-q2 / 0.0000 / 0.0000 / 0.0000 / 0.0000 / 0.0000 / 0.0000
s-w-q1 / 0.6066 / 1.3358 / 0.5973 / 0.5072 / 0.5894 / 0.4707
d-r-f1 / 3.7016 / 7.8397 / 4.0038 / 3.6022 / 3.6392 / 3.6888
d-w-f2 / 0.9595 / 3.2063 / 1.1940 / 0.8360 / 0.8174 / 3.6017
d-w-f1 / 1.0489 / 4.6164 / 1.1027 / 0.9964 / 0.9340 / 1.0087