Acta Phys. -Chim. Sin. ›› 2015, Vol. 31 ›› Issue (2): 211-220.doi: 10.3866/PKU.WHXB201412231


Intermolecular Interaction Induced Multi-Polymers of Aceclofenac with Flexible Conformation: Crystal Structure, Thermostability, Solubility and DFT Calculations

SUN Pan-Pan1, LIU Xiang-Yu1,2, SUN Lin2, ZHANG Sheng1, WEI Qing1, YIN Yan1, YANG Qi1, CHEN San-Ping1   

  1. 1. Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi'an 710069, P. R. China;
    2. School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021, P. R. China
  • Received:2014-10-30 Revised:2014-12-22 Published:2015-01-26
  • Contact: CHEN San-Ping, WEI Qing,;
  • Supported by:

    The project was supported by the National Natural Science Foundation of China (21373162, 21463020, 21073142, 21173168) and Natural Science Foundation of Shaanxi Province, China (11JS110, 2013JM2002, SJ08B09).


The non-steroidal anti-inflammatory drug aceclofenac (ACF) has low bioavailability because of its poor water solubility. To enhance its water solubility we synthesized three compounds: a co-crystal of ACF- 0.5BIPY (4,4'-bipyridine) (1), a salt of ACF-3-ABA (3-aminobenzoic acid) (2), and a solvate of ACF-DMSO (dimethyl sulfoxide) (3). These compounds were characterized by infrared spectroscopy, powder and single crystal X-ray diffractions. The supramolecular structures of 1-3 are sustained by hydrogen bonding C―H…π and ππ stacking interactions and they have favorable thermal stabilities. Thermodynamically, DFT calculations revealed that the most stable conformation of ACF exists in compound 3 and this structure is more stable than 1 and 2. Furthermore, upon the formations of the co-crystal, the salt or the solvate the solubility of ACF improves significantly.

Key words: Aceclofenac, Multi-polymer, Thermostability, Density functional theory, Solubility