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

Table 5 Total energies, Gibbs free energies (298 K), and structural properties for the σ-complexes, x-Ac,x-H ⁺

Substituent	Total energy E (a.u.)	G₂₉₈(a.u.)	G₂₉₈relative to 4- Ac,4-H⁺(kJ mol⁻¹)	θ^a(degrees)
2-Ac,2-H⁺	−694.942784	−694.702831	7.3	24.9
4-Ac,4-H⁺	−694.945838	−694.705627	0	23.3
5-Ac,5-H⁺	−694.929221	−694.692290	35.0	36.8
6-Ac,6-H⁺	−694.944629	−694.705485	0.4	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