Solution growth and thermal treatment of crystals lead to two new forms of 2-((2,6-dimethylphenyl)amino)benzoic acid

Rong Hu, Yunping Zhoujin, Meng Liu, Mingtao Zhang, Sean Parkin, Panpan Zhou, Jianzhi Wang, Faquan Yu, Sihui Long

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

We report the discovery of two new forms (II and III) of a potential non-steroidal anti-inflammatory and thyroid drug, 2-((2,6-dimethylphenyl)amino)benzoic acid (HDMPA) through solution growth and thermal treatment of crystals. Form II has been discovered through crystal growth in a variety of solvents, and characterized by single-crystal X-ray diffraction, powder X-ray diffraction (PXRD), FT-IR, and Raman spectroscopy. Form II converts into form III upon thermal treatment, as indicated by the phase behavior study of form II with differential scanning calorimetry (DSC). Form III has been characterized by IR, Raman and PXRD. Conformational flexibility of the molecule seems to lead to the polymorphism of the system. A conformational scan shows the conformational minima correspond to the conformers in the polymorphs. Lattice energy calculations show energies of -48.14 and -50.31 kcal mol-1 for forms I and II, providing information on the relative stability for each form. Hirshfeld analysis revealed that intermolecular interactions such as C⋯C, H⋯H, C⋯H, and H⋯O contribute to the stability of the crystal forms.

Original languageEnglish
Pages (from-to)15459-15470
Number of pages12
JournalRSC Advances
Volume8
Issue number28
DOIs
StatePublished - 2018

Bibliographical note

Funding Information:
RH and SL thanks Natural Science Foundation of Hubei Province (2014CFB787) and the President's Fund of Wuhan Institute of Technology (CX2016075) for nancial support. PPZ acknowledges the nancial support by the National Natural Science Foundation of China (Grant No. 21403097) and the Fundamental Research Funds for the Central Universities (lzujbky-2016-45).

Publisher Copyright:
© The Royal Society of Chemistry 2018.

ASJC Scopus subject areas

  • Chemistry (all)
  • Chemical Engineering (all)

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