Combined experimental and computational modeling studies on 3,5‐dimethyl‐pyrazole‐1‐carbodithioic acid benzyl ester

Abstract

ABSTRACT:The title compound, 3,5-Dimethyl-pyrazole-1-carbodithioic acid benzyl ester, has been synthesized and structurally characterized by X-ray single crystal diffraction, elemental analysis, IR spectra, and UV-Vis spectrum. The crystal belongs to orthorhombic, space group P212121, with a ¼ 5.3829(15), b ¼ 11.193(3), c ¼ 21.824(6) Å , V ¼ 1315.0(6) Å 3 , and Z ¼ 4. The molecules are connected via intermolecular C-HÁÁÁN hydrogen bonds into 1D infinite chains. The crystal structure is consolidated by the intramolecular C-HÁÁÁS hydrogen bonds. Furthermore, Density functional theory (DFT) calculations of the structure, stabilities, orbital energies, composition characteristics of some frontier molecular orbitals and Mulliken charge distributions of the title compound were performed by means of Gaussian 03W package and taking B3LYP/ 6-31G(d) basis set. The time-dependent DFT (TD-DFT) calculations have been employed to calculate the electronic spectrum of the title compound, and the UV-Vis spectra has been discussed on this basis. The results show that DFT method at B3LYP/6-31G(d) level can well reproduce the structure of the title compound.

Dithiocarbamate RAFT agents with broad applicability – the 3,5-dimethyl-1H-pyrazole-1-carbodithioates

“…The benzyl derivative has been previously prepared by condensation of 2,4-pentanedione with benzyl hydrazinecarbodithioate. [42][43][44] Tertiary dithiocarbamates (e.g., 20) can be prepared by radical-induced decomposition of the bis(thioacyl) disulfide, where radicals are conveniently generated from the appropriate dialkyldiazene. [45][46][47] The use of these RAFT agents was explored in polymerization of DMA, MMA, MA, St and VAc.…”

4-Halogeno-3,5-dimethyl-1H-pyrazole-1-carbodithioates: versatile reversible addition fragmentation chain transfer agents with broad applicability

“…Density functional theory calculations have recently been carried out for similar 3,5‐dimethylpyrazole compounds and their associated metal complexes . In the present work, we use higher‐level ab initio molecular orbital calculations to assess qualitatively the relative reactivities of pyrazole and non‐pyrazole dithiocarbamates.…”