Molecular structure analysis of the chlorhexidine salts
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Date
2023-10-15
Journal Title
Journal ISSN
Volume Title
Publisher
Elsevier. B. V
Abstract
Novel organic salts comprising of chlorhexidine di-cation (CHX) with perchlorate H2CHX(ClO4)2·2H2O (CHXPC) and hydrogen citrate H2CHX(C6H6O7).H2O (CHXHC) were prepared, and their crystal structures studied. Despite extensive applications of chlorhexidine as an antimicrobial agent, CHXPC and CHXHC are amongst just a few reported crystal structures containing CHX that have been characterized so far. Exhibiting different structural patterns in their crystal packing, the CHXPC and CHXHC was distinguishable from one another with U- and S- shaped conformations, respectively. Their wide variety of hydrogen bonds were investigated from different point of views, among which were the overall structure of the salts, di-cations and oxyanions, and also their capability of forming 2D- and 3D-frameworks of hydrogen bonding. In addition, multifurcated multi-centered hydrogen bonding, such as bifurcated three-centered and trifurcated four-centered hydrogen bonds were observed in the structures of CHXPC and CHXHC as well. In comparison with normal single hydrogen bonding, the multifurcated hydrogen bonding indicated more flexibility with arrangements in their geometry. The hydrogen bonds containing oxygen-oxygen as donor and acceptor (O ̶ H···O) were employed to estimate their acidity (pKa) and strength (EHB) with different directionality. Hirshfeld surface analysis (HSA) was also used to confirm the intermolecular interactions in the structures of CHXPC and CHXHC. © 2023 Elsevier B.V.
Description
Preprint version from SSRN attached.
Keywords
Salts, Crystal structure, Hydrogen, Bonding, Surfaces, Dentistry, Diseases
Citation
Rashidnejad, H., Ramezanitaghartapeh, M., Mokarizadeh, M., Price, J. R., Söhnel, T., & Mahon, P. J. (2023). Molecular structure analysis of the chlorhexidine salts. Journal of Molecular Structure, 1290, 135830. doi:10.1016/j.molstruc.2023.135830