Table 3.
Total energy, dipole moment, frontier molecular HOMO and LUMO orbitals, gap value, and descriptors for 1–4 in gas phase, obtained by using the B3LYP/6-311++G(d,p) method.
| 1 | 2 | 3 | 4 | |
|---|---|---|---|---|
| enol-imine tautomer | ||||
| Total energy (eV) | −19,255.75967 | −22,372.91079 | −89,285.41965 | −24,822.27922 |
| Dipole moment (Debye) | 3.279813 | 4.290475 | 4.070018 | 6.97922 |
| EHOMO (eV) | −0.23040 | −0.21087 | −0.23196 | −0.26088 |
| ELUMO (eV) | −0.06421 | −0.06388 | −0.07426 | −0.09961 |
| ΔELUOMO–HOMO = ELUMO−EHOMO (eV) | 0.16619 | 0.14699 | 0.15770 | 0.16127 |
| Ionization energy, I = −EHOMO (eV) | 0.23040 | 0.21087 | 0.23196 | 0.26088 |
| Electron affinity, A = −ELUMO (eV) | 0.06421 | 0.06388 | 0.07426 | 0.09961 |
| Electronegativity, χ = (I + A)/2 (eV) | 0.14731 | 0.13738 | 0.15311 | 0.18025 |
| Chemical potential, μ = −χ (eV) | −0.14731 | −0.13738 | −0.15311 | −0.18025 |
| Global chemical hardness, η = (I−A)/2 (eV) | 0.08310 | 0.07350 | 0.07885 | 0.08064 |
| Global chemical softness, S = 1/(2η) (eV−1) | 6.01721 | 6.80318 | 6.34115 | 6.20078 |
| Global electrophilicity index, ω = μ2/(2η) (eV) | 0.13057 | 0.12839 | 0.14865 | 0.20145 |
| Global nucleophilicity index, E = μ × η (eV2) | −0.01224 | −0.01010 | −0.01207 | −0.01453 |
| Maximum additional electric charge, ΔNmax = −μ/ƞ | 1.77273 | 1.86917 | 1.94179 | 2.23532 |
| cis-keto-enamine tautomer | ||||
| Total energy (eV) | −19,255.55920 | −22,372.72632 | −89,285.24115 | −24,822.17304 |
| Dipole moment (Debye) | 5.623354 | 6.171161 | 6.678792 | 10.089039 |
| EHOMO (eV) | −0.20510 | −0.19161 | −0.20980 | −0.23553 |
| ELUMO (eV) | −0.07356 | −0.07108 | −0.08356 | −0.10179 |
| ΔELUOMO–HOMO = ELUMO−EHOMO (eV) | 0.13154 | 0.12053 | 0.12624 | 0.13374 |
| Ionization energy, I = −EHOMO (eV) | 0.20510 | 0.19161 | 0.20980 | 0.23553 |
| Electron affinity, A = −ELUMO (eV) | 0.07356 | 0.07108 | 0.08356 | 0.10179 |
| Electronegativity, χ = (I + A)/2 (eV) | 0.13933 | 0.13135 | 0.14668 | 0.16866 |
| Chemical potential, μ = −χ (eV) | −0.13933 | −0.13135 | −0.14668 | −0.16866 |
| Global chemical hardness, η = (I−A)/2 (eV) | 0.06577 | 0.06027 | 0.06312 | 0.06687 |
| Global chemical softness, S = 1/(2η) (eV−1) | 7.60225 | 8.29669 | 7.92142 | 7.47719 |
| Global electrophilicity index, ω = μ2/(2η) (eV) | 0.14758 | 0.14313 | 0.17043 | 0.21270 |
| Global nucleophilicity index, E = μ × η (eV2) | −0.00916 | −0.00792 | −0.00926 | −0.01128 |
| Maximum additional electric charge, ΔNmax = −μ/ƞ | 2.11844 | 2.17946 | 2.32383 | 2.52221 |
| trans-keto-enamine tautomer | ||||
| Total energy (eV) | −19,255.22025 | −22,372.44811 | −89,284.91121 | −24,821.82359 |
| Dipole moment (Debye) | 7.396322 | 7.781535 | 7.644000 | 10.221661 |
| EHOMO (eV) | −0.20158 | −0.19035 | −0.20722 | −0.23080 |
| ELUMO (eV) | −0.07988 | −0.07497 | −0.08963 | −0.11216 |
| ΔELUOMO–HOMO = ELUMO−EHOMO (eV) | 0.12170 | 0.11538 | 0.11759 | 0.11864 |
| Ionization energy, I = −EHOMO (eV) | 0.20158 | 0.19035 | 0.20722 | 0.23080 |
| Electron affinity, A = −ELUMO (eV) | 0.07988 | 0.07497 | 0.08963 | 0.11216 |
| Electronegativity, χ = (I + A)/2 (eV) | 0.14073 | 0.13266 | 0.14843 | 0.17148 |
| Chemical potential, μ = −χ (eV) | −0.14073 | −0.13266 | −0.14843 | −0.17148 |
| Global chemical hardness, η = (I−A)/2 (eV) | 0.06085 | 0.05769 | 0.05880 | 0.05932 |
| Global chemical softness, S = 1/(2η) (eV−1) | 8.21693 | 8.66701 | 8.50412 | 8.42886 |
| Global electrophilicity index, ω = μ2/(2η) (eV) | 0.16274 | 0.15253 | 0.18735 | 0.24785 |
| Global nucleophilicity index, E = μ × η (eV2) | −0.00856 | −0.00765 | −0.00873 | −0.01017 |
| Maximum additional electric charge, ΔNmax = –μ/ƞ | 2.31274 | 2.29953 | 2.52445 | 2.89076 |