Table 2. Results from a Binding Energy Decomposition Using (Second-Order Intramonomer/Third-Order Intermonomer) Symmetry-Adapted Perturbation Theory (SAPT2+(3)/aug-cc-pVDZ) for the π-Stacking Homodimers of 2-Naphthalenethiol, Naphthalene, 1-Naphthol, and Thiophenol and Several Hydrogen-Bonded Dimers, Comparing the Magnitude of the Attractive Contributions and Stabilization Energiesa.
| ΔEElectrostatic | ΔEInduction | ΔEDispersion | ΔEExchange | ΔETotal | |
|---|---|---|---|---|---|
| (H2S)2b | –12.1 [49.0%]c | –4.8 [19.4%] | –7.8 [31.6%] | 19.3 | –5.4 |
| (H2O)2 | –35.7 [63.4%] | –11.1 [19.7%] | –9.5 [16.9%] | 37.7 | –18.6 |
| (Phenol)2 | –41.8 [48.3%] | –15.9 [18.4%] | –28.8 [33.3%] | 58.9 | –27.6 |
| (1-Naphthol)2 | –33.4 [27.5%] | –11.0 [9.1%] | –77.1 [63.5%] | 80.2 | –41.3 |
| (Naphthalene)2 | –20.5 [21.4%] | –7.0 [7.3%] | –68.1 [71.2%] | 65.2 | –30.3 |
| (2-Naphthalenethiol)2 | –34.1 [26.7%] | –8.8 [6.9%] | –84.7 [66.4%] | 80.1 | –47.5 |
| (Thiophenol)2 | –26.2 [29.8%] | –8.4 [9.6%] | –53.3 [60.6%] | 61.0 | –26.9 |
a
All values in kJ mol–1.
b
The dimer structures were optimized at B3LYP-D3(BJ)/def2-TZVP level.
c
The values in square brackets represent the relative percentage with respect to the total attractive interactions.