News
27.05.2022Publication of the article "Static discrete disorder in the crystal structure of iododiflunisal: on the importance of hydrogen bond, halogen bond and π-stacking interactions
PhD. Rafel Prohens, head of the Polymorphism and Calorimetry Laboratory of the CCiTUB, together with PhD. Rafael Barbas and PhD. Mercè Font, CCiTUB technicians, have published the article entitled " Static discrete disorder in the crystal structure of iododiflunisal: on the importance of hydrogen bond, halogen bond and π-stacking interactions " in the journal CrystEngComm (indexed in the JCR within the Q1 quartile of the Crystallography area, and with an impact factor of 3.55).
The article, in which researchers from the University of Oviedo, the Institute of Advanced Chemistry of Catalonia and the University of the Balearic Islands have also participated, is the result of the methodological development studies that are carried out in the Polymorphism and Calorimetry laboratory.
The abstract of the paper is the following:
"This manuscript reports a combined computational/crystallographic analysis of iododiflunisal (IDIF), a difluorophenyl derivative of salicylic acid (2′,4′-difluoro-4-hydroxy-5-iodo-[1,1′]-biphenyl-3-carboxylic acid). This drug is used to target transthyretin related amyloidosis. In the solid state it shows static discrete disorder and forms the typical R22(8) centrosymmetric dimer that is common in carboxylic acids (via double OH⋯O H-bonds). Parallel face-to-face stacking interactions are also observed in its crystal packing where these R22(8) centrosymmetric dimers are propagated forming infinite 1D columns. Moreover, the presence of iodine, which exhibits a region of large and positive electrostatic potential (σ-hole) along the C–Ha bond and a belt of negative electrostatic potential (σ-lumps) facilitates the formation of halogen bonds (HaBs) and halogen⋯halogen contacts that are also relevant in the solid state. The crystalline disorder was analyzed by means of Hirshfeld surfaces, and hydrogen, halogen and π–π bonding assemblies were analyzed using density functional theory (DFT) calculations, molecular electrostatic potential (MEP) surfaces, the quantum theory of “atom-in-molecules” (QTAIM) and the noncovalent interaction plot (NCIplot)."
The paper can be read at the follwing link:[+].