Bifunctionalization of α,β-unsaturated diaryl ketones into α-aryl-,β, β-ditosyloxy ketones: Single crystal XRD, DFT, FMOs, molecular electrostatic potential, hirshfeld surface analysis, and 3D-energy frameworks

Environmentally benign synthesis, structural explication by means of IR, H-1 & C-13 NMR, HRMS and crystal structure of two electronically different alpha-aryl-beta, beta-ditosyloxy ketones i.e., 2-(4-methylphenyl)-3-oxo-3-phenylpro-pane-1,1-diyl bis(4-methylbenzenesulfonate) (C30H28O7S2) (5a) and 3-(4-fluorophenyl)-2-(4-methoxyphenyl)-3-oxopropane-1,1-diyl bis(4-methylbenzene-sulfonate) (C30H27FO8S2) (5b) have been successfully described here. Both alpha-aryl-beta,beta-ditosyloxy ketones 5a and 5b crystallized in the monoclinic crystal system with P21/n and P21/c space group respectively. Single crystal XRD-analysis unraveling the oxidative skeletal rearrangement in alpha,beta-unsaturated diaryl ketones and outcome of reaction introduced the synthetic community with still unrecognized and excellent 1,3-dielectrophilic precursors i.e., alpha-aryl-beta,beta-ditosyloxy ketones. Density functional theory (DFT), HOMO-LUMO, 3D-hirshfeld surface analysis, 2D-finger plots, molecular electrostatic potential (MEPs) and 3D-interaction energies have been performed and discussed with an objective to study the physical properties of these new 1,3-dielectrophilic three carbon atom components before their utilization as a chemical precursor in heterocycles synthesis like alpha,beta-dibromo analogues. (C) 2021 Elsevier B.V. All rights reserved.