Table 3.
Interaction energies (ΔE, in kcal/mol) of complexes 1 to 20 at the BP86-D3/def2-TZVPP level of theory. The intermolecular distances and angles (d and α, in Å and °, respectively) corresponding to the HlgB, lp-π, and ancillary interactions, as well as the values of the density at the bond critical point that characterizes the HlgB and lp-π and ancillary interactions (ρ × 100, in a.u.), are also indicated.
| Complex (Material@VOC) |
ΔE | ΔE per HlgB | d * | d *CH-π (HC···CH) | α | ρ × 100 | ρ × 100 CH-π (CH···HC) |
|---|---|---|---|---|---|---|---|
| 1 (Cl-PDI@MeOH) | −8.1 | −4.1 | 3.053 | 3.074 | 160.3 | 0.99 | 0.49 |
| 2 (Cl-PDI@EtOH) | −9.3 | −4.7 | 3.074 | 3.024 | 169.2 | 0.84 | 0.60 |
| 3 (Cl-PDI@PrOH) | −10.4 | −5.2 | 2.976 | 3.138 | 171.3 | 1.08 | 0.54 |
| 4 (Cl-PDI@BuOH) | −10.4 | −5.2 | 3.290 | 2.806 | 146.6 | 0.58 | 0.60 |
| 5 (Br-PDI@MeOH) | −8.4 | −4.2 | 3.054 | 2.849 | 159.9 | 1.07 | 0.58 |
| 6 (Br-PDI@EtOH) | −11.3 | −5.7 | 3.073 | 3.048 | 167.5 | 1.04 | 0.59 |
| 7 (Br-PDI@PrOH) | −13.3 | −6.7 | 2.953 | 3.183 | 174.2 | 1.38 | 0.52 |
| 8 (Br-PDI@BuOH) | −12.2 | −6.1 | 3.186 | 3.126 | 159.5 | 0.85 | 0.34 |
| Complex | ΔE * | ΔE per lp-π | d * | d *CH-π (HC···CH) | ρ × 100 | ρ × 100 CH-π (CH···HC) | |
| 9 (Cl-PDI@MeOH) | −15.0 | −7.5 | 2.918 | 3.120 | 1.07 | 0.65 | |
| 10 (Cl-PDI@EtOH) | −16.9 | −8.5 | 2.828 | 2.641 (3.622) | 0.88 | 0.46 (0.37) | |
| 11 (Cl-PDI@PrOH) | −22.5 | −11.3 | 2.842 | 3.075 (3.907) | 0.76 | 0.81 (0.51) | |
| 12 (Cl-PDI@BuOH) | −23.0 | −11.5 | 2.787 | 2.765 (3.598) | 1.00 | 0.75 (0.58) | |
| 13 (Br-PDI@MeOH) | −15.5 | −7.8 | 2.924 | 2.915 | 1.08 | 0.60 | |
| 14 (Br-PDI@EtOH) | −19.7 | −9.9 | 3.070 | 2.863 (3.460) | 0.84 | 0.64 (0.68) | |
| 15 (Br-PDI@PrOH) | −22.8 | −11.4 | 2.833 | 2.845 (3.912) | 0.76 | 0.87 (0.51) | |
| 16 (Br-PDI@BuOH) | −22.8 | −11.4 | 2.781 | 2.794 (3.595) | 0.98 | 0.71 (0.53) | |
| 17 (PDI@MeOH) | −7.2 | −3.6 | 2.904 | 2.783 | 1.22 | 0.77 | |
| 18 (PDI@EtOH) | −15.1 | −7.6 | 2.878 | 2.873 | 1.13 | 0.57 | |
| 19 (PDI@PrOH) | −18.9 | −9.5 | 3.066 | 2.829 (3.875) | 0.87 | 0.71 (0.59) | |
| 20 (PDI@BuOH) | −21.3 | −10.7 | 2.960 | 2.704 (3.730) | 1.04 | 0.77 (0.53) | |
*(1) Values given as the shortest distance between the VOC and the PDI moiety. In the case of the HC···CH interactions, only those cases where the C···C distance was lower than 4 Å were considered. *(2) The values corresponding to complexes 9 to 20 encompass the lp-π and CH-π interactions. The contribution of the CH-HC interactions between the two alcohol alkyl chains was subtracted from the complex (see Section 3 below).