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Table 4 Total energies, Gibbs free energies (298 K), and structural properties for the acetyl substituted 4-acetyl-3,3′-dimethylbiphenyls, 4,y′-diAc

From: A reactivity-selectivity study of the Friedel-Crafts acetylation of 3,3′-dimethylbiphenyl and the oxidation of the acetyl derivatives

Substituents

Total energy E (a.u.)

G298(a.u.)

G298relative to 4,5′- diAc (kJ mol−1)

θa(degrees)

ϕb(degrees)

     

4-Ac

y′-Ac

4,2′-diAc

−847.247523

−846.984334

35.3

48.2

0.1

61.5

4,4′-diAc

−847.256356

−846.992372

14.2

36.5

1.0

1.0

4,5′-diAc

−847.259523

−846.997775

0

36.7

0.7

0.4

4,6′-diAc

−847.250427

−846.988520

24.3

53.0

0.6

32.4

  1. Results from DFT B3LYP 6-31 G(d,p) calculations. aDihedral angle between the two benzene rings taken as the average of the C2-C1-C1′-C6′ and C6-C1-C1′-C2′ dihedral angles. bDihedral angle between the carbonyl group and the benzene ring to which it is attached taken as the CAr-CAr-C = O dihedral angle.