Investigations based on non-covalent interactions in 1-(4-chloromethylbenzoyl)-3-(4, 6-di-substituted pyrimidine-2-yl)thioureas: Synthesis, characterizations and quantum chemical calculations

Abstract

1-(4-chloromethylbenzoyl)-3-(4, 6-di-substituted pyrimidine-2-yl)thioureas (1 and 2) have been synthesized using the reaction of 4-chloromethylbenzoyl isothiocyanate with 4-chloro-6-methoxypyrimidine-2-amine and 4, 6-di-methylpyrimidine-2-amine in dry tetrahydrofuran. The two compounds were characterized by FT-IR and FT-Raman (vibrational spectra), multinuclear (1H and 13C) NMR, single crystal X-ray diffraction, mass spectrometry and elemental analyses techniques. The reduced density gradient (RDG) function, which provides abundant visualization as a wide range of real space, was used to analysis the intramolecular non-covalent interactions. Besides, non-covalent interactions were discovered by us in title compounds, including hydrogen bonds, CH--lone pairs, O⋯S, van der Waals interactions and steric/ring closure effects. Hirshfeld surfaces and their two-dimensional fingerprint plots were performed to explain the intermolecular interactions in crystal lattice. The vibrational spectra (FT-IR and FT-Raman), as well as the NBO analysis have been studied using the B3LYP/6–311++G (d, p) level of approximation.