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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.