Synthesis, Crystal Structure and Spectral Characterization of 5-Methyl-2-(Propan-2-yl)Cyclohexyl Cyanoacetate and 1,3,3-Trimethylbicyclo[2.2.1]Heptan-2-yl Cyanoacetate
aChemistry Department, Faculty of Science, Ain Shams University, Cairo, Egypt
bFaculty of Chemistry, Wrocław University of Science and Technology, Wrocław, Poland
cGreen Chemistry Department, National Research Centre, Cairo, Egypt
email: *fatmasalaheldin@yahoo.com
email: **julia.bakowicz@pwr.edu.pl
email: ***blazej.dziuk@pwr.edu.pl
email: ****gnawwar@yahoo.com
Received 28 August, 2024
Abstract— The titled compounds are synthesized using a conventional esterification method, involving the reaction of the desired alcohol with cyanoacetic acid. Single crystal is obtained through recrystallization. The compounds are characterized using elemental analysis, IR, 1H NMR, 13C NMR spectroscopy, and mass spectrometry. The structural parameters, including bond distances and angles, are analyzed and discussed based on X-ray study result. The study reveals that the hydrogen atoms of the methylene groups in the two synthesized compounds exhibit a rigid C–H rotating group. The absolute configuration of the stereogenic centers in both compounds is consistent with the substrate used in their synthesis.
Keywords: cyanoacetylation, menthol, fenchol, menthyl cyanoacetate, fenchyl cyanoacetate, crystal structure, X-ray study.
DOI: 10.1134/S0022476625020167