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Structural, Spectroscopic and Thermal Analysis of Cocrystals of Carbamazepine and Piracetam with Hydroquinone

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Abstract

Cocrystals of two important active pharmaceutical ingredients, carbamazepine and piracetam, with hydroquinone are reported. Cocrystal formation between the selected APIs and hydroquinone is investigated with the aid of solid-state grinding methods. Both the crystal structures belong to the triclinic, \(P \bar{1}\) space group, with the cocrystal involving carbamazepine and hydroquinone having the unit cell parameters a = 6.9725 (14) Å, b = 8.8175 (18) Å, c = 15.083 (3) Å, α = 106.96 (3)°, β = 92.16 (3)°, γ = 103.23 (3)°, V = 858.0 (4) Å3 and Z = 2; and the cocrystal involving piracetam and hydroquinone has the unit cell parameters a = 6.4909 (13) Å, b = 6.5410 (13) Å, c = 11.612 (2) Å, α = 103.92 (3)°, β = 104.53 (3)°, γ = 91.06 (3)°, V = 461.59 (18) Å3 and Z = 2. Analysis of the cocrystals revealed that they are sustained by an alcohol–carboxamide heterosynthon. In addition, the cocrystal of carbamazepine and hydroquinone features an amide–alcohol heterosynthon and an alcohol–alcohol homosynthon. The cocrystal of piracetam and hydroquinone features an amide–amide dimer synthon. Cocrystal formation was evidenced from the shifts in the vibrational frequencies corresponding to the functional groups present on the cocrystal components.

Graphical Abstract

Cocrystals of carbamazepine and piracetam with hydroquinone were prepared, and characterized by FT-IR spectroscopy, thermal analysis, and powder and single-crystal X-ray diffraction. Analysis of the crystal structures revealed that both the cocrystals are sustained by alcohol–amide heterosynthon and the cocrystal involving piracetam and hydroquinone features an amide–amide dimer synthon.

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Acknowledgement

This work was supported by Science and Engineering Research Council of A*STAR (Agency for Science, Technology and Research), Singapore.

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Authors and Affiliations

  1. Institute of Chemical and Engineering Sciences, Agency for Science, Technology and Research (A*STAR), 1 Pesek Road, Jurong Island, 627833, Singapore

    Srinivasulu Aitipamula, Pui Shan Chow & Reginald B. H. Tan

  2. Department of Chemical and Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, Singapore, 117576, Singapore

    Reginald B. H. Tan

Authors
  1. Srinivasulu Aitipamula
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  2. Pui Shan Chow
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  3. Reginald B. H. Tan
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Correspondence to Srinivasulu Aitipamula or Reginald B. H. Tan.

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Aitipamula, S., Chow, P.S. & Tan, R.B.H. Structural, Spectroscopic and Thermal Analysis of Cocrystals of Carbamazepine and Piracetam with Hydroquinone. J Chem Crystallogr 41, 1604–1611 (2011). https://doi.org/10.1007/s10870-011-0147-y

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  • DOI: https://doi.org/10.1007/s10870-011-0147-y

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