B3LYP/6-31G*a | ||||||
Parameter | 2-Hydroxy-4,6-dimethylpyridine-3-carbonitrile | 2-Chloro-4,6-dimethylpyridine-3-carbonitrile | Exp.b | |||
| Gas phase | PCM | Gas phase | PCM | ||
Bond lengths (Å) | ||||||
C1-C2 | 1.412 | 1.411 | 1.410 | 1.405 |
| |
C2-C3 | 1.407 | 1.409 | 1.411 | 1.413 | 1.383 | |
C3-C12 | 1.505 | 1.501 | 1.505 | 1.501 | 1.493 | |
C3-C4 | 1.397 | 1.395 | 1.395 | 1.394 | 1.384 | |
C4-C5 | 1.397 | 1.397 | 1.397 | 1.396 | 1.383 | |
C5-C8 | 1.505 | 1.501 | 1.504 | 1.499 | 1.501 | |
C1-N7 | 1.325 | 1.324 | 1.314 | 1.312 | 1.327 | |
C5-N7 | 1.345 | 1.350 | 1.347 | 1.353 | 1.346 | |
C2-C16 | 1.427 | 1.422 | 1.428 | 1.425 | 1.426 | |
C16-N17 | 1.164 | 1.167 | 1.163 | 1.166 | 1.145 | |
C1-O18/C1-Cl18 | 1.345 | 1.352 | 1.754 | 1.764 |
| |
RMSD | 0.004 | 0.004 | 0.005 | 0.005 |
| |
Bond angles (˚) | ||||||
C1-C2-C3 | 117.8 | 118.3 | 117.6 | 117.6 |
| |
C2-C3-C4 | 117.5 | 117.1 | 117.3 | 117.0 | 121.8 | |
C2-C3-C12 | 120.7 | 121.0 | 120.8 | 121.0 | 121.5 | |
C4-C3-C12 | 121.6 | 121.8 | 121.7 | 121.9 | 120.0 | |
C4-C5-N7 | 121.9 | 122.1 | 121.6 | 121.5 |
| |
C4-C5-C8 | 121.8 | 121.3 | 122.2 | 121.8 | 121.8 | |
C8-C5-N7 | 116.1 | 116.5 | 116.1 | 116.5 | 115.2 | |
C2-C1-O18/Cl18 | 118.3 | 117.6 | 119.0 | 118.8 |
| |
N7-C1-O18/Cl18 | 117.6 | 118.4 | 116.4 | 116.1 |
| |
C2-C16-N17 | 178.1 | 179.7 | 177.2 | 178.6 | 178.7 | |
C3-C2-C16 | 121.3 | 121.6 | 120.1 | 120.6 | 120.0 | |
C1-C2-C16 | 120.8 | 119.9 | 122.2 | 121.6 |
| |
RMSD | 0.7 | 0.8 | 0.7 | 0.8 |
| |
Dihedral angle (˚) | ||||||
C1-C2-C16-N17 | 179.9 | 179.9 | 180.0 | 180.0 |
| |
C3-C2-C16-N17 | −0.0 | −0.0 | 0.0 | 0.0 | −94.0 | |
C3-C2-C1-O18 | 180.0 | −179.9 | 180.0 | 180.0 |
| |
C5-N7-C1-O18 | −180.0 | −179.9 | 180.0 | 180.0 |
| |
C1-C2-C3-C12 | 179.9 | 179.9 | 180.0 | 180.0 |
| |
C1-N7-C5-C8 | −179.9 | 179.9 | 180.0 | 180.0 | −179.2 | |
C3-C4-C5-C8 | 179.9 | −180.0 | 180.0 | 180.0 | 179.1 | |
C5-C4-C3-C12 | −179.9 | −179.9 | 180.0 | 180.0 | 179.1 | |
RMSD | 92.7 | 157.2 | 92.8 | 92.8 |
| |