Synthesis, crystallographic characterization, DFT and TD-DFT studies of Oxyma-sulfonate esters

Abstract

Three oxyma sulfonate esters were prepared using dichloromethane-water (two-phase method) in the presence of sodium carbonate for scavenging HCl. The products were characterized by FT-IR, NMR ( 1 H and 13 C), UV-Vis spectra and elemental analysis. X-ray single crystal diffraction experiments proved the molecular structures of three esters. Their molecular structures were also calculated using DFT/B3LYP method. The optimized structures agreed well with the X-ray structures. Time-dependent density functional theory (TD-DFT) was used to assign the electronic absorption bands observed experimentally. Pyridine derivative showed two bands at shorter λmax compared to the others, both experimentally and theoretically. The NMR chemical shifts were computed for protons and carbons using GIAO method, which correlated well with the experimental data. Natural charges, dipole moments and chemical reactivity of these molecules, as well as their non-linear optical activity, were computed and compared.

The Synthesis of Molecular Probes Based on Cystic Fibrosis Drugs for Biological Research

“…A mixed solvent system was used in entry 6 along with the inorganic base according to the literature. 139 An efficient method for tosylating alcohol was reported by Yoshida 140 using an amine base with a catalytic amount of Me3N•HCl was also attempted (entry 7) and still, no formation of 4.14 was observed.…”

“…Trifluoroketone 133,[141][142][143] and cyanoketone 139 substrates which are somewhat similar to 4.13 are commonly tosylated in high yield. Hence, it appears that the presence of electron-withdrawing groups influences the tosylation of the oxime.…”

Copper(II)-Dioxygen Facilitated Activation of Nitromethane: Nitrogen Donors for the Synthesis of Substituted 2-Hydroxyimino-2-phenylacetonitriles and Phthalimides

“…Cyano-oxime compounds and their derivatives have shown tremendous potentials for the development of a variety of biological compounds such as herbicides, drugs, and antibacterial agents (Gerasimchuk et al, 2008;El-Faham et al, 2014). The presence of two important functional groups in a single molecule makes them widely applicable for the synthesis of nitrogenous organic compounds in chemical engineering (Robertson et al, 2005;Aakeröy et al, 2012;Soliman et al, 2017). Of these, 2-hydroxyimino-2phenylacetonitriles (2) are useful building blocks for the construction of polynitrogen organic substances, especially for the synthesis of peptides and/or nitrogen-containing heterocyclic compounds (Itoh et al, 1975;Kunai et al, 1990;Neel and Zhao, 2018;Alam et al, 2020).…”