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