Table 2.

Experimentally determined binding free energy for phenol derivatives

		catechol	phenol
Phenol analogs	ΔGb,exp (Kcal/mol)	ΔGb,calc (Kcal/mol)	ΔGb,calc(Kcal/mol)	PDB IDs
2-propylphenol	−5.33 ± 0.05	−6.13	−3.05	3HTB
phenol	−5.24	–	–	1LI2
5-chloro-2-methylphenol	−5.04 ± 0.07	−7.54	−1.32	3HT8
2-ethylphenol	−4.57 ± 0.11	−5.15	−1.14	3HT7
2-methylphenol	−4.44 ± 0.11	−4.31	−2.55	3HT6
catechol	−4.16 ± 0.03	–	−4.88†	1XEP
2-ethoxyphenol	−4.02 ± 0.03	−4.16	−4.25	3HU8
2-methoxyphenol	> −2.0*	−2.76	−3.84	3HT9

Reference ligands are in italics. Free energy of binding determined by ITC at 10°C;

^*indicates the binding free energy was estimated as ΔG_b ≥ −2.0. The binding free energies for the six phenol derivatives are shown; for each compound ΔG_b,calc was calculated from the predicted relative binding free energy and the experimentally determined ΔG_b of the reference compounds catechol or phenol.

^†The corrected retrospective result for the phenol to catechol transformation is given (described in Results: Analysis of predictions).