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

Table 6 Total energies, Gibbs free energies (298 K), and structural properties for the σ-complexes, 4-Ac,y′-Ac,y′-H ⁺

Substituent	Total energy E (a.u.)	G₂₉₈(a.u.)	G₂₉₈relative to 4-Ac,4′- Ac,4′-H⁺(kJ mol⁻¹)	θ^a(degrees)
4-Ac,2′-Ac,2′-H⁺	−847.582972	−847.310553	6.6	31.8
4-Ac,4′-Ac,4′-H⁺	−847.585556	−847.313061	0	23.9
4-Ac,5′-Ac,5′-H⁺	−847.571021	−847.300305	33.5	36.5
4-Ac,6′-Ac,6′-H⁺	−847.584905	−847.312773	0.8	32.3

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.

ISSN: 2661-801X