Table 2.
Calculateda structural characteristics for the planar and twisted geometries of 1.
| carbonyl geometry |
singlet root |
ΔHf (kcal/mol) |
dipole (D) |
bond order |
charge |
||
|---|---|---|---|---|---|---|---|
| CAr-N | C=O | N | O | ||||
| planarb | 1 | −21.7 | 7.8 | 1.12 | 1.80 | −0.29 | −0.42 |
| planar | 2 | 49.9 | 15.7 | 1.22 | 1.68 | −0.09 | −0.48 |
| planar | 3 | 57.3 | 12.8 | 1.18 | 1.71 | −0.16 | −0.46 |
| twistedc | 1 | −19.9 | 6.4 | 1.11 | 1.84 | −0.30 | −0.40 |
| twisted | 2 | 56.2 | 11.5 | 1.23 | 1.83 | −0.08 | −0.40 |
| twisted | 3 | 62.0 | 26.0 | 1.31 | 1.24 | −0.10 | −0.70 |
a
Using DMSO for the solvent.
b
Carbonyl constrained to 0° dihedral angle.
c
Carbonyl constrained to 90° dihedral angle.