Abstract
The whole mol-ecule of the title compound, C20H14O6, is generated by mirror symmetry, the mirror bis-ecting the central benzene ring. The carbonate groups adopt an s-cis-s-cis conformation, with torsion angles of 58.7 (2) and 116.32 (15)°. The crystal structure of 1,3-phenyl-ene bis-(phenyl carbonate) contains no strong hydrogen bonds, though weak C-H⋯O and offset π-π inter-actions are observed, forming layers parallel to the ac plane.
Highlights
The whole molecule of the title compound, C20H14O6, is generated by mirror symmetry, the mirror bisecting the central benzene ring
Alternative preparatory methods include the reaction of alcohols and carbon monoxide in the presence of a catalyst, direct condensation of alcohols and carbon dioxide (Joe et al, 2012; Zhang et al 2012; Zhao et al, 2009), or the alcoholysis of urea (Ball et al, 1980; Bhanage et al, 2003; Zhang et al, 2016; Mote & Ranade, 2017)
The bis(phenyl carbonate) structure reported was identified as an unexpected side product from the attempted recrystallization of 1-(m-phenol)-3-phenylurea from ethanol
Summary
Supporting information: this article has supporting information at journals.iucr.org/e. Organic carbonates have a wide range of applications as polymers, surfactants, fuel additives, solvents for complex industrial syntheses and extractions, and even medical agents, dyes, and foodstuff (Shukla & Srivastava, 2017). The bis(phenyl carbonate) structure reported was identified as an unexpected side product from the attempted recrystallization of 1-(m-phenol)-3-phenylurea from ethanol. We surmise this compound formed through a combination of intermolecular ‘self-alcoholysis’ reactions leading to a carbamate intermediate (Mote & Ranade, 2017), which subsequently over time yields the title compound, 1,3-phenylene bis(phenyl carbonate). Analysis of the relatively limited number of diaryl carbonate structures previously reported shows that the title compound shares some of the same structural features
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