Click Chemistry-Based Synthesis, Characterization, and DFT Studies of Some Novel 2-Acetylphenoxy-1,2,3-Triazoles

Abstract

A series of the new 1,2,3-triazole-acetophenone hybrid system are synthesized from the click reaction between 1-(2-(prop-2-yn-1-yloxy)phenyl)ethan-1-one 1 and different azido benzene derivatives 2-7. All compounds are characterized by 1H NMR, 13C NMR, mass spectra, and elemental analyses. Field Emission Scanning Electron Microscope (FESEM) detected highly ordered aggregations, and the morphology of the compounds was determined, directed by van der Waals (vdW) forces and π-π stacking interactions. The Gaussian 09 and Gaussian view 6.0 softwares are used for all Density Functional Theory (DFT) calculations at the B3LYP. Band gap, molecular softness, electronegativity, and electrophilicity measurements show that molecule 9 is a soft molecule with higher polarizability, lower kinetic stability, and more chemical reactivity than the other molecules, which tend to be the most stable and least reactive. The molecules can be divided into two categories based on their chemical potential values: Although compound 9 looks to have more activity, compounds 8, 10, 11, 12, and 13 often have the best stability and least reactivity. According to the MEPs, the nitrogen and oxygen atoms are the electronegative potential sites in all compounds, while the hydrogen atoms in the alkyl and aromatic cyclic groups are the electropositive potential sites.