Oehlke, Alexander; Auer, Alexander A.; Jahre, Ina; Walfort, Bernhard; Rueffer, Tobias; Zoufala, Petra; Lang, Heinrich; Spange, Stefan published the artcile< Nitro-substituted stilbeneboronate pinacol esters and their fluoro-adducts. Fluoride ion induced polarity enhancement of arylboronate esters>, HPLC of Formula: 112-63-0, the main research area is boronate dioxaborolane stilbene nitro derivative preparation complexation fluoride anion; formation constant equilibrium fluoride addition boronate nitrostilbene derivative; UV vis spectra solvatochromism nitrostilbene boronate derivative fluoride adduct; solvent effect Kamlet Taft equation boronate nitrostilbene fluoride adduct; optimized mol structure dioxaborolane stilbene nitro derivative fluoride adduct; excitation energy vertical dioxaborolane stilbene nitro derivative fluoride adduct; bond length conjugate dioxaborolane stilbene nitro derivative fluoride adduct; hydrogen bonding solvent dioxaborolane stilbene nitro derivative fluoride adduct; electron density NBO dioxaborolane stilbene nitro derivative fluoride adduct; crystal structure dioxaborolane stilbene nitro derivative; mol structure dioxaborolane stilbene nitro derivative.
A series of stilbeneboronate pinacol cyclic esters, containing none to three nitro groups, (E)-(CMe2O)2B-1,4-C6H4CH:CHC6Hn(NO2)5-n-2,4,6 (3-6; n = 0-3) were prepared by Horner-Emmons-Wadsworth olefination of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (2) or by condensation of 2 with 2,4-dinitrophenylacetic acid or 2,4,6-trinitrotoluene. Compounds 3-6 were characterized by x-ray single-crystal structure anal. Compounds 3-6 undergo reversible and solvent-dependent addition of fluoride ion by reaction with Bu4NF, forming adducts 3路F–6路F-; the equilibrium systems feature isosbestic points in UV-vis. spectra. A stilbeneboronate ester bearing electron-acceptor groups experiences transition to a push-pull 蟺-electron system upon complexation with one fluoride ion at the boron atom. The UV-vis absorption maxima of the presented nitro-substituted stilbeneboronate esters are red-shifted upon addition of fluoride ions, indicating this binding event. The enhancement of the polarity of the investigated compounds and the changes in the electronic system were investigated by UV-vis absorption spectroscopy and solvatochromism. Addnl., studies were performed by natural bond orbital (NBO) anal. and RI-CC2 calculations of the vertical excitation energies. The synergism of fluoride ion complexation and solvation upon the UV-vis band shift is interpreted in terms of linear solvation energy relationships (LSERs) using the Kamlet-Taft solvent parameter set. It is found that the UV-vis absorption of the fluoro-boronates is strongly dependent on the solvents hydrogen-bond donating ability.
Journal of Organic Chemistry published new progress about Aromatic hydrocarbons Role: FMU (Formation, Unclassified), PEP (Physical, Engineering or Chemical Process), PRP (Properties), SPN (Synthetic Preparation), FORM (Formation, Nonpreparative), PROC (Process), PREP (Preparation) (stilbenes, boronates). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, HPLC of Formula: 112-63-0.
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