Synthesis, Characterization, and Structural Investigations of 1-(3-morpholinopropyl)-3-(4-chlorobenzoyl)thiourea monohydrate and 1-(3-morpholinopropyl)-3-(4-methylbenzoyl)thiourea monohydrate

Abstract

Two new compounds, 1-(3-morpholinopropyl)-3-(4-chlorobenzoyl)thiourea monohydrate (I) and 1-(3-morpholinopropyl)-3-(4-methylbenzoyl)thiourea monohydrate (II) have been synthesized and characterized by FT-IR, ¹H NMR, ¹³C NMR, and Single-Crystal X-Ray Diffraction analyses. Theoretical investigations have been calculated by using DFT method of B3LYP/6-31G + (2d,p) and B3LYP/6-311G + (2d,p) basis sets. Each compound contains a water molecule, forming intra and intermolecular hydrogen bonds with other molecules and further stabilizes the crystal structure. Theoretical calculations of bond parameters, harmonic vibration frequencies, and isotropic chemical shifts are in good agreement with the experimental results. The observed intermolecular interactions in the crystal packing are the main cause of the calculated torsion angles, molecular vibrations, and chemical shifts. The calculated molecular vibrations show good correlation values ranging from 0.995, 0.996, and 0.997 with the experimental data, where the higher basis set fits the experimental results better.

Keywords:

• Crystal Structure
• DFT Studies
• Spectroscopy
• Thiourea

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and USM Short Term Grant, No. 304/PFIZIK/6312078 and FRGS Grant 59178 to conduct this work. SA thanks the Malaysian government and USM for the Academic Staff Training Scheme Fellowship (ASTS).