Building a library of monofluorinated anilino-methylidenes and spectroscopic studies of their properties

Conformational, Spectroscopic, and Molecular Dynamics DFT Study of Precursors for New Potential Antibacterial Fluoroquinolone Drugs

“…The UV−vis spectra of the investigated compounds in CHCl 3 and dimethyl sulfoxide (DMSO) were recorded using a UV−vis−NIR UV 3600 spectrophotometer (Shimadzu, Japan) with a 1 cm square quartz cell. All NMR spectra were measured on the Agilent 600 MHz VNMRS spectrometer operating at frequencies 600 and 150 MHz for 1 H, 19 F, and 13 C nuclei and on an Agilent 300 MHz VNMRS spectrometer operating at frequencies 300 and 75 MHz for 1 H, 19 F, and 13 C nuclei. All details of FT-IR, UV− vis, and NMR measurements are described in Plevováet al 19…”

“…All NMR spectra were measured on the Agilent 600 MHz VNMRS spectrometer operating at frequencies 600 and 150 MHz for 1 H, 19 F, and 13 C nuclei and on an Agilent 300 MHz VNMRS spectrometer operating at frequencies 300 and 75 MHz for 1 H, 19 F, and 13 C nuclei. All details of FT-IR, UV− vis, and NMR measurements are described in Plevováet al 19…”

“…Following the experimentally measured UV−vis spectra, the characteristic absorption band of the studied precursors is found in the range of 300−350 nm. 19 This transition can be formally assigned to the n→π* (HOMO→LUMO) excitation in the α, β-unsaturated carbonyl chromophore (C α C β −CO) containing two coupled carbonyl centers. 58 The experimental 19 and calculated absorption maxima and the oscillator strengths are summarized in Table 6.…”

“…17,18 Newly synthesized 3-fluoroquinolones have been prepared from precursors bounded with different substituents R 1 and R 2 , such as −COOC 2 H 5 , −COOCH 3 , and −COCH 3 . 19 The structure of these precursors of fluoroquinolones is summarized in Table 1. In accordance with the literature data, 20,21 previous quantumchemical studies were oriented exclusively toward the spectroscopic and tautomeric characterization of quinolones.…”

“…In accordance with the literature data, 20,21 previous quantumchemical studies were oriented exclusively toward the spectroscopic and tautomeric characterization of quinolones. A closer theoretical study of (fluoro)quinolone precursors using standard DFT computational protocols and a subsequent comparison to the experiment 19 has not been carried out yet. The fluoroquinolone precursors are well-known as push−pull ethylenes.…”