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Propeller-like Conformation of Diphenylacetic Acid

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Abstract

Crystal structure of diphenylacetic acid has been solved by X-ray diffraction. The crystals are monoclinic, space group P21/c, with a = 12.254(4) Å, b = 7.2260(8) Å, c = 17.521(4) Å, β = 133.38(1)°, Mr = 212.24, V = 1127.6(5) Å3, Z = 4 and R = 0.045. A strong hydrogen bond links the molecules in dimers. The dimers are connected by weaker C–H···π and π···π interactions. A calculation was performed for the isolated molecule and for the dimer within the Hartree-Fock (HF) level with a 6-311G(d) basis set. In both calculations, the minimum of the energy is achieved with the phenyl rings assuming a more symmetric arrangement around the central carboxylic plane than is experimentally observed.

Graphical Abstract

In diphenylacetic acid the molecules are coupled in dimers by a strong hydrogen bonds. Weaker intermolecular interactions involving the aromatic ring π systems join the dimers together.

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Acknowledgement

This work was supported by Fundação para a Ciência e a Tecnologia under project POCI/FIS/57876/2004.

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Authors and Affiliations

  1. CEMDRX Physics Department, University of Coimbra, Rua Larga, Coimbra, 3004-516, Portugal

    Manuela Ramos Silva, Ana Matos Beja, Jose A. Paixão & Sergio R. Domingos

  2. CFC, Physics Department, University of Coimbra, Coimbra, 3004-516, Portugal

    Claudia Cardoso

Authors
  1. Manuela Ramos Silva
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  2. Claudia Cardoso
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  3. Ana Matos Beja
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  4. Jose A. Paixão
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  5. Sergio R. Domingos
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Corresponding author

Correspondence to Manuela Ramos Silva.

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Silva, M.R., Cardoso, C., Beja, A.M. et al. Propeller-like Conformation of Diphenylacetic Acid. J Chem Crystallogr 38, 403–406 (2008). https://doi.org/10.1007/s10870-007-9311-9

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  • DOI: https://doi.org/10.1007/s10870-007-9311-9

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