Synthesis and properties of aromatic 1,3-diketones and bis-(1,3-diketones) obtained from acetophenone and phtalic acids esters

Zawadiak, Jan; Mrzyczek, Marek; Piotrowski, Tomasz

doi:10.5155/eurjchem.2.3.289-294.416

Cited by 14 publications

(8 citation statements)

References 9 publications

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“…119 Sn NMR spectra of the complexes show signals in the region −148.33 to −183.34. 119 Sn NMR chemical shift values are summarized in Table and reveal the presence of pentacoordinated tin centres in these dimethyltin(IV) complexes as reported earlier …”

Section: Resultssupporting

confidence: 68%

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Investigation of pharmacophore and antipharmacophore features of certain dimethyltin(IV) complexes of flexible N‐protected amino acids and fluorinated β‐diketone/β‐diketones

Maheshwari

Srivastava

Saxena

et al. 2016

Applied Organom Chemis

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A set of pentacoordinated dimethyltin(IV) complexes of flexible N‐protected amino acids and fluorinated β‐diketone/β‐diketones was screened for their antibacterial activity against Pseudomonas aeruginosa, Staphylococcus aureus and Streptomyces griseus. These pentacoordinated complexes of the type Me2SnAB (where : R = CH(CH3)C2H5, A1H; CH2CH(CH3)2, A2H; CH(CH3)2, A3H; CH2C6H5, A4H; and BH = R'C(O)CH2C(O)R″: R′ = C6H5, R″ = CF3, B1H; R′ = R″ = CH3, B2H; R′ = C6H5, R″ = CH3, B3H; R′ = R″ = C6H5, B4H) were generated by the reactions of dimethyltin(IV) dichloride with sodium salts of flexible N‐protected amino acids (ANa) and fluorinated β‐diketone/β‐diketones (BNa) in 1:1:1 molar ratio in refluxing dry benzene solution. Plausible structures of these complexes were elucidated on the basis of physicochemical and spectral studies. 119Sn NMR spectral data revealed the presence of pentacoordinated tin centres in these dimethyltin(IV) complexes.

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Section: Resultssupporting

confidence: 68%

“…Table 4 and reveal the presence of pentacoordinated tin centres in these dimethyltin(IV) complexes as reported earlier. [32][33][34] The proposed structure of dimethyltin(IV) complexes of flexible N-protected amino acids and fluorinated βdiketone/β-diketones is as follows:…”

Section: H Nmr Spectramentioning

confidence: 99%

Investigation of pharmacophore and antipharmacophore features of certain dimethyltin(IV) complexes of flexible N‐protected amino acids and fluorinated β‐diketone/β‐diketones

Maheshwari

Srivastava

Saxena

et al. 2016

Applied Organom Chemis

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“…Tautomerisms are structural isomers that differ from one another on the basis of the position of proton(s) and double bonds; the carbon skeleton of the structure is unchanged [ 1 ]. It was first described by Laarin in 1886 [ 2 ].Keto-enol tautomerism in β-ketoester [ 3 , 4 , 5 ], β-diketones[ 6 , 7 , 8 , 9 ], β-ketonitrile [ 10 ], β-ketoamide [ 11 , 12 , 13 ], ortho-hydroxy Schiff bases [ 14 , 15 , 16 , 17 ], Azo dyes [ 18 ], alpha-ketophosphonates [ 19 ], and the 1,3,4-thiadiazole group with a 2,4-hydroxyphenyl function [ 20 ] have been studied using different spectroscopic techniques. Similarly, those compounds of type β-keto-enol derivatives containing heterocyclic moieties such as 4-hydroxycoumarin [ 21 ], Imidazoline derivatives [ 22 ], indol [ 23 ], and pyrazole, pyridine, thiophene, or furan [ 24 ] can exist as a keto-enol tautomerism.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopic Studies and Keto-Enol Tautomerism of Novel 1,3,4-Thiadiazole Derivative Containing 3-Mercaptobutan-2-one and Quinazolin-4-one Moieties

et al. 2020

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In this study, a novel 1,3,4-thiadiazole derivative containing 3-mercaptobutan-2-one and quinazolin-4-one moieties (Compound 3) is synthesized by the coupling of 2-amino-1,3,4-thiadiazole-5-(3-mercaptobutan-2-one) (Compound 1) with 2-Phenyl-4H-3,1-benzoxazin-4-one (Compound 2) in one molecule moiety. Compound 3 is found to exist as two types of intra-molecular hydrogen bonding with keto-enol tautomerism characters, which is further confirmed using FTIR, 1H-NMR, 13C-NMR, mass spectrometer, and UV-Visible spectra. The 1H-NMR and UV-Visible spectra of Compound 3 are investigated in different solvents such as methanol, chloroform, and DMSO. Compound 3 exhibits keto-enol tautomeric forms in solvents with different percentage ratios depending on the solvent polarity. The 1H-NMR and UV-Visible spectral results show that Compound 3 favors the keto over the enol form in polar aprotic solvents such as DMSO and the enol over the keto form in non-polar solvents such as chloroform. The 13C-NMR spectrum gives two singles at δ 204.5 ppm, due to ketonic carbon, and δ 155.5 ppm, due to enolic carbon, confirming the keto-enol tautomerism of Compound 3. Furthermore, the molecular ion at m/z 43 and m/z 407 in the mass spectrum of Compound 3 and fragmentation mechanisms proposed reveal the existence of the keto and enol forms, respectively.

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“…1 H NMR shifts are listed excepting the tautomeric protons. Synthesis of all compounds has been described previously: DBM , 1 , 12 , 2–7 , 10 , 11 , 13–15 , 8 , 9 , 16 , and 17 …”

Section: Methodsmentioning

confidence: 99%

Correlation of substituted aromatic β‐diketones' characteristic protons chemical shifts with Hammett substituent constants

Zawadiak

Mrzyczek

2013

Magnetic Reson in Chemistry

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Influence of dibenzoylmethane's substituents in meta and para positions on chemical shift values of tautomers' characteristic protons was investigated in four solvents with (1)H NMR spectroscopy: acetone-d(6), benzene-d(6), CDCl(3) and deuterated dimethyl sulfoxide (DMSO-d(6)). It was proved that the influence of substituents on chemical shifts strongly depends on the kind of the solvent; the greatest changes were observed in benzene-d6 and the smallest in CDCl(3). In acetone-d(6) and DMSO-d(6), the influence of substituents on chemical shifts is similar and the most regular. It allowed a fair correlation of chemical shifts of para-substituted dibenzoylmethane derivatives' characteristic protons with Hammett substituent constants in these solvents. In CDCl(3), characteristic protons' chemical shifts were near (1)H NMR spectroscopy measurement error limits, and, therefore, correlation with Hammett substituent constants in this solvent was unsatisfactory. In benzene, although the changes of chemical shifts are the most evident, the changes are also the most irregular, and, therefore, correlation in this solvent failed completely. Results of meta-substituted derivatives were much more irregular, and their correlation with Hammett substituent constants was poor in all investigated solvents.

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Synthesis and properties of aromatic 1,3-diketones and bis-(1,3-diketones) obtained from acetophenone and phtalic acids esters

Cited by 14 publications

References 9 publications

Investigation of pharmacophore and antipharmacophore features of certain dimethyltin(IV) complexes of flexible N‐protected amino acids and fluorinated β‐diketone/β‐diketones

Investigation of pharmacophore and antipharmacophore features of certain dimethyltin(IV) complexes of flexible N‐protected amino acids and fluorinated β‐diketone/β‐diketones

Synthesis, Spectroscopic Studies and Keto-Enol Tautomerism of Novel 1,3,4-Thiadiazole Derivative Containing 3-Mercaptobutan-2-one and Quinazolin-4-one Moieties

Correlation of substituted aromatic β‐diketones' characteristic protons chemical shifts with Hammett substituent constants

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