Thione tautomer of mono-cyclohexyl-substituted bismuthiol: Synthesis and structure elucidation, characteristic vibrations, thermal behavior, and biological activity
Document Type
Article
Publication Date
1-15-2024
Abstract
A new derivative of 2-cyclohexyl-substituted bismuthiol was synthesized via a sequential one-pot procedure in ethanol under reflux conditions. After many trials, the long colorless needle-like crystals could be isolated, suitable for X-ray crystallography. The chemical structure of the new bismuthiol derivative was characterized by spectroscopic techniques. The characteristic vibrations for differentiation of thiol-thione tautomers were defined regarding the comparative FTIR study of bismuthiol and two of its derivatives viz mono- and bis-cyclohexylsubstituted bismuthiol. The presence of a hyper-conjugative interaction between the S-H and pi bond of C=N was indicated. In addition, the existence of C=S and C-N-H for the new product was demonstrated through single crystal XRD analysis, which supports thiol or thione tautomer determination using IR spectra. The TGA/ DTA and DSC profiles of bismuthiol and mono- and bis-cyclohexyl-substituted bismuthiol were studied to determine the influence of hydrogen bonding, packing, and symmetric and unsymmetric structure on the transition phases and thermal stability. Finally, the biological activity of bismuthiol and bis- and monocyclohexyl-substituted bismuthiols were screened in silico by SwissADME tool and in vitro against the gramnegative (Escherichia coli ATCC 25,922) and gram-positive (Staphylococcus aureus ATCC 25,923) bacterial species.
Keywords
Heterocycles, Crystal structure, X-ray structure determination, Structure-activity relationship, Thermal behavior, Biological activity
Divisions
nanocat,advanced
Funders
Ministry of Higher Education (MOHE) , Malaysia [IIRG004A-2022FNW],Nippon Sheet Glass Foundation for Materials Science and Engineering, Japan [IF008-2023]
Publication Title
Journal of Molecular Structure
Volume
1296
Issue
2
Publisher
Elsevier
Publisher Location
RADARWEG 29, 1043 NX AMSTERDAM, NETHERLANDS