Structural studies of enantiomers, racemates, and quasiracemates. 2-(2,4-dichlorophenyl)propanoic acid and 2-(2-chloro-4-nitrophenyl)propanoic acid

Add time:07/30/2019    Source:sciencedirect.com

Cocrystallization of a 1:1 solution of (R)-2-(2,4-dichloro)phenoxypropanoic acid and (S)-2-(2-chloro-4-nitro)phenoxypropanoic acid yields quasiracemic crystals. The principal quasiracemate components (sterically similar, differing in chirality and Cl/NO2 substitutions) assemble to form pseudosymmetric heterodimers linked by carboxylic acid O-H⋅⋅⋅O R22(8) interactions. A comparison of the structure of the quasiracemate to the individual enantiomers and the “true” racemates provides a means to probe the influence of molecular topologies on the observed molecular recognition behavior. These results show that the orientation of discrete assemblies for the quasiracemate can be controlled predictably by topological influences. Preferred molecular orientations and key structural features of these systems have been examined in context of the imposed Cl and NO2 structural differences.

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