Fig 1.
Optimized structures of 7 compounds with orthodiphenolic functionalities calculated at the B3LYP/6-311++G(d,p) level in ethanol.
(left: a hydrogen bond is formed between the 4-O• center and the meta OH. right: no hydrogen bond is formed between the 4-O• center and the meta OH.)
Fig 2.
The energy difference (ΔE in kcal/mol) caused by the hydrogen bond between the O• center and the meta OH for 7 radicals calculated at the B3LYP/6-311++G(d,p) levels of theory in 4 reaction media.
Table 1.
BDEs of 20 investigated phenolic compounds and phenol calculated at the B3LYP/6-311++G(d,p) level a.
Fig 3.
Spin density values of phenoxy radicals of 20 investigated phenolic compounds and phenol calculated at the B3LYP/6-311++G(d,p) levels of theory in ethanol.
Table 2.
Absolute (E in kcal/mol) and relative energies (ΔE in kcal/mol) of various hydrogen atom-abstracted radicals in 4 reaction environments calculated at the B3LYP/6-311++G(d, p) levels of theorya.
Table 3.
IPs and PDEs of 20 investigated phenolic compounds and phenol calculated at the B3LYP/6-311++G(d,p) level a.
Table 4.
PAs and ETEs of 20 investigated phenolic compounds and phenol calculated at the B3LYP/6-311++G(d,p) level a.
Fig 4.
HOMO of 20 investigated phenolic compounds calculated at the B3LYP/6-311++G(d,p) levels of theory in ethanol.
The numbers indicates atomic polar tensor charges.
Table 5.
QSAR modeling results of the thermodynamics-activity relationship for 20 phenolic compounds in water and ethanol a.