Phenyl 3,5-di-tert-butyl-2-hydroxybenzoate

What is it about?

The title mol­ecule, C21H26O3, has a six-membered planar carbon ring as the central core, substituted at position 1 with phen­oxy­carbonyl, at position 2 with hy­droxy and at positions 3 and 5 with tert-butyl groups. The structure shows two independent but very similar mol­ecules within the asymmetric unit. For both independent mol­ecules, the ester carboxyl­ate group is coplanar with the central core, as reflected by the small C-C-O-C torsion angles [179.95 (17) and 173.70 (17)°]. In contrast, the phenyl substituent is almost perpendicular to the carboxyl­ate -CO2 fragment, as reflected by C-O-C-C torsion angles, ranging from 74 to 80°. The coplanarity between the central aromatic ring and the ester carboxyl­ate -CO2- group allows the formation of an intra­molecular hydrogen bond, with O...O distances of 2.563 (2) and 2.604 (2) Å.

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Why is it important?

Other important studies in bioinspired compounds are focused in the search of new dyes to be used as photoelectrochemical devices, such as porphyrin macrocycles containing benzimidazole subunits, including a phenol group with an intramolecular hydrogen bond, which exhibit a chemically reversible couple that undergoes photoinduced electron transfer.