2. Academic Validation
  3. Variation of Activation Volume as an Indicator of the Difference in Clusterization Phenomenon Induced by H-Bonding and F-Π Stacking Interactions in Enantiomers and a Racemate of Flurbiprofen

Variation of Activation Volume as an Indicator of the Difference in Clusterization Phenomenon Induced by H-Bonding and F-Π Stacking Interactions in Enantiomers and a Racemate of Flurbiprofen

  • J Phys Chem B. 2024 Apr 25;128(16):4021-4032. doi: 10.1021/acs.jpcb.4c00582.
Paulina Jesionek 1 2,  Barbara Hachuła 1,  Karolina Jurkiewicz 3,  Patryk Włodarczyk 4,  Marek Hreczka 4 5,  Kamil Kamiński 3,  Ewa Kamińska 2
Affiliations

Affiliations

  • 1 Institute of Chemistry, Faculty of Science and Technology, University of Silesia in Katowice, Szkolna 9, 40-007 Katowice, Poland.
  • 2 Department of Pharmacognosy and Phytochemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, Jagiellonska 4, 41-200 Sosnowiec, Poland.
  • 3 Institute of Physics, Faculty of Science and Technology, University of Silesia in Katowice, 75 Pulku Piechoty 1, 41-500 Chorzow, Poland.
  • 4 Łukasiewicz Research Network - Institute of Non-Ferrous Metals, Sowinskiego 5 St., 44-100, Gliwice, Poland.
  • 5 Department of Mechatronics, Silesian University of Technology, Akademicka 10A St., 44-100 Gliwice, Poland.
PMID: 38608273 DOI: 10.1021/acs.jpcb.4c00582
Abstract

In this paper, X-ray diffraction (XRD), differential scanning calorimetry (DSC), broadband dielectric (BDS), and Fourier transform infrared (FTIR) spectroscopy supported by molecular dynamics (MD) simulations and quantum chemical computations were applied to investigate the structural and thermal properties, molecular dynamics, and H-bonding pattern of R-, S-, and RS-flurbiprofen (FLP). Experimental data indicated various spatial molecular arrangements in crystalline forms of examined systems, which seemed to disappear in the liquid state. Surprisingly, deeper analysis of high-pressure dielectric data revealed unexpected variation in the activation volume of pure enantiomers and a racemate. MD simulations showed that it is an effect of the clusterization phenomenon and a higher population of small associates in the former samples. Moreover, theoretical consideration exposed the particular role of unspecific F-Π interactions as a driving force underlying local molecular arrangements of molecules in the liquid and the crystal lattice of R-, S-, and RS-FLP.

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