Isomerizational and conformational study of 3-fluorophenylamino-2-acetyl propenenitrile (FPAAPN)

Gatial, A.; Dorotíková, Sandra; Plevová, Kristína; Milata, Viktor; Prónayová, Nadežda; Matějka, Pavel

doi:10.1016/j.molstruc.2014.12.056

Cited by 4 publications

(2 citation statements)

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“…For NC-substituted enaminones, the CH proton of the N–CH moiety has 3 J H,CN coupling with the cyano group in the range of 4.6–5.8 Hz and 9.6–10.8 Hz for their cis - and trans -orientation, respectively. 18 Also in the literature the 3 J H,C O coupling has been measured 19 for similar structures, alkoxymethylidenediones ( cis - 3 J H,C O = 2.6–4.0 Hz, trans - 3 J H,C O = 7.7–10.1 Hz) and the magnitudes of these 3 J H,C O coupling constants are convenient parameters for establishment of enaminodione configuration in our case. It was found that for enaminodione 3b the carbonyl group of the aroyl substituent (C-4′) is a quartet at δ 193.0 ppm with 3 J H,C = 3.7 Hz, which indicates the cis -arrangement of the H-6 proton relative to C-4′ ( Fig.…”

Section: Resultsmentioning

confidence: 81%

Synthesis of novel polycarbonyl Schiff bases by ring-opening reaction of ethyl 5-acyl-4-pyrone-2-carboxylates with primary mono- and diamines

et al. 2019

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Section: Resultsmentioning

confidence: 81%

Synthesis of novel polycarbonyl Schiff bases by ring-opening reaction of ethyl 5-acyl-4-pyrone-2-carboxylates with primary mono- and diamines

et al. 2019

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“…The conformations of both acetyl groups strongly depend on the possibility to create stabilizing intramolecular hydrogen bond between the electron-donor group, e.g. amino group H 2 N- (Gróf, 2007) or alkylamino group R-NH- (Gatial, 2015) and carbonyl of the cis acetyl group. The conformers with such bond belong to the most stable ones.…”

Section: Introductionmentioning

confidence: 99%

Raman and infrared spectra, conformations and ab initio calculations of 3-methoxymethylene-2,4-pentanedione

Gatial

Milata

Prónayová

et al. 2015

Acta Chimica Slovaca

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The IR (4000-400 cm-1) and Raman (4000-50 cm-1) spectra of 3-methoxymethylene-2,4-pentanedione [H3C-O-CH=C(COCH3)2] as a liquid and solutes in various solvents of different polarity have been recorded at ambient temperature. Additional IR and Raman spectra were obtained for amorphous and crystalline solid state at low temperature. The vibrational spectra revealed that the compound exists at least in two dominant conformers of different polarity and that the conformer present in the solid phase is less polar. NMR spectra in various solvents at different temperatures were also obtained. The compound can exist in several conformers due to the rotation around O-C= and both =C-C bonds with planar or nonplanar arrangements of heavy atoms. Ab initio MP2 and DFT calculations using a wide scale of basis sets were carried out. According to these calculations six conformational structures of the eight theoretically possible conformational structures with the methoxy group oriented as anti or syn and carbonyl groups oriented as Z or E towards the C=C double bond were obtained at potential energy surface. It has been shown that the conformers with the E orientations of both acetyl groups are not the stable ones. The calculated ab initio MP2 and DFT energies of all found conformers in vacuum suggest the most stable ZEa conformer where Z and E regard to the trans and cis acetyl groups, respectively and a denotes the orientation of the methoxy group. The EZa conformer was calculated as the second most stable one with the energy by at least 10 kJ mol-1 higher. Corrections of the relative energies of single conformers obtained in vacuum on the polar surroundings were done by including the solvent effect into the calculations using IEF Polarizable Continuum Model. Assignments of the vibrational spectra for the studied compound were made with the aid of normal coordinate calculations employing scaled ab initio force field. The scaled ab initio frequencies as well as calculated energies indicate that ZEa is the conformer present in the solid phase.

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Joined X-ray, spectroscopic and theoretical study of potential antibacterial cyano group containing fluoroquinolone drugs precursors with the focus on the conformational behavior

Dorotíková

Kucková

Malček

et al. 2016

Journal of Molecular Structure

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Isomerizational and conformational study of 3-fluorophenylamino-2-acetyl propenenitrile (FPAAPN)

Cited by 4 publications

References 36 publications

Synthesis of novel polycarbonyl Schiff bases by ring-opening reaction of ethyl 5-acyl-4-pyrone-2-carboxylates with primary mono- and diamines

Synthesis of novel polycarbonyl Schiff bases by ring-opening reaction of ethyl 5-acyl-4-pyrone-2-carboxylates with primary mono- and diamines

Raman and infrared spectra, conformations and ab initio calculations of 3-methoxymethylene-2,4-pentanedione

Joined X-ray, spectroscopic and theoretical study of potential antibacterial cyano group containing fluoroquinolone drugs precursors with the focus on the conformational behavior

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