The vibrational spectra and structures of dimethyl oxaloacetate and dimethyl oxaloacetate-d2

Schiering, David W.; Katon, J. E.

doi:10.1016/0584-8539(86)80044-7

Cited by 8 publications

(3 citation statements)

References 23 publications

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“…Dimethyl oxaloacetate ester exhibits, as reported in the literature [13], complete enolization in the crystal phase. Being a 1,3-dicarbonyl compound, in solution it exists as an equilibrium mixture of keto and enol forms, the proportionation depending on the polarity of the solvent.…”

Section: Product Studies On the Cl-atom -Initiated Oxidation Of Dimetmentioning

confidence: 61%

FT‐IR kinetic and product study of the OH radical and Cl‐atom–initiated oxidation of dibasic esters

Cavalli

Barnes

Becker

2001

Int J of Chemical Kinetics

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Using a relative kinetic technique, rate coefficients have been measured, at 296 Ϯ 2 K and 740 Torr total pressure of synthetic air, for the gas-phase reaction of OH radicals with the dibasic esters dimethyl succinate [CH 3 ; and dimethyl adipate (6.08 Ϯ 0.86) ϫ 10 Ϫ11. Dibasic esters are industrial solvents, and their increased use will lead to their possible release into the atmosphere, where they may contribute to the formation of photochemical air pollution in urban and regional areas. Consequently, the products formed from the oxidation of dimethyl succinate have been investigated in a 405-L Pyrex glass reactor using Cl-atom-initiated oxidation as a surrogate for the OH radical. The products observed using in situ Fourier transform infrared (FT-IR) absorption spectroscopy and their fractional molar yields were: succinic formic anhydride (0.341 Ϯ 0.068), monomethyl succinate (0.447 Ϯ 0.111), carbon monoxide (0.307 Ϯ 0.061), dimethyl oxaloacetate (0.176 Ϯ 0.044), and methoxy formylperoxynitrate (0.032-0.084). These products account for 82.4 Ϯ 16.4% C of the total reaction products. Although there are large uncertainties in the quantification of monomethyl succinate and dimethyl oxaloacetate, the product study allows the elucidation of an oxidation mechanism for dimethyl succinate.

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Section: Product Studies On the Cl-atom -Initiated Oxidation Of Dimetmentioning

confidence: 61%

FT‐IR kinetic and product study of the OH radical and Cl‐atom–initiated oxidation of dibasic esters

Cavalli

Barnes

Becker

2001

Int J of Chemical Kinetics

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“…The symmetric and asymmetric stretching peaks of CH2 of keto forms in the -ketoesters are observed at high frequencies, as well as two strong peaks in the region of about 1700 cm -1 are related to stretching vibrations (C=O) of keto forms of -ketoesters [21,37].Also keto forms in the CH2 stretching region are not distinguishable in AA [36]. Usually, in the -ketoesters most of the frequencies generated in the keto form tend to be blueshift.…”

Section: Molecular Geometry and Intramolecular H-bond Strengthmentioning

confidence: 95%

“…vibrations, These bands in Raman spectrum of AA was observed at about 1719-1697 cm -1 , while the mentioned bands in IR spectra of -ketoesters with a blueshift is appeared at 1740-1720 cm -1 . Schiering et al reported the band of 1759 cm -1 in the CCl4 IR spectra DMOA for C=O stretching vibration methoxy group in enol form [37].…”

Section: Molecular Geometry and Intramolecular H-bond Strengthmentioning

confidence: 99%

Comparison of Tautomerization, Vibrational Spectra and UV-Vis Analysis of β-Ketoester With Acetylacetone. An Experimental and Theoretical Study

Aval¹,

Pour²,

Vakili³

et al. 2021

Preprint

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In this study, the equilibrium constants, keto-enol ratio, and hydrogen bond strength among keto and cis-enol forms of acetylacetone (AA), methyl acetoacetate (MAA), ethyl acetoacetate (EAA), ethyl 2-methyl acetoacetate (EMA), benzyl acetoacetate (BAA), and ethyl benzoyl acetone (EBA) have been investigated using density functional theory (DFT), compared with the experimental results. According to the obtained results, the relative energy of cis-enol and keto forms of β-ketoesters in gas phases is greater than that of acetylacetone, so the enol form of acetylacetone is more stable and it causes to increase its strength of intramolecular hydrogen bond. The electronic properties of these compounds were surveyed by NMR, FT-IR, and UV-Vis spectra. Besides, the obtained outcomes showed that the keto forms of β-ketoesters in the presence of acetonitrile and carbon tetrachloride as a solvent have a high absorption coefficient due to the polarity of the solvent.

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NMR, IR, conformation and hydrogen bonding

Floris

1990

PATAI'S Chemistry of Functional Groups

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The vibrational spectra and structures of dimethyl oxaloacetate and dimethyl oxaloacetate-d2

Cited by 8 publications

References 23 publications

FT‐IR kinetic and product study of the OH radical and Cl‐atom–initiated oxidation of dibasic esters

FT‐IR kinetic and product study of the OH radical and Cl‐atom–initiated oxidation of dibasic esters

Comparison of Tautomerization, Vibrational Spectra and UV-Vis Analysis of β-Ketoester With Acetylacetone. An Experimental and Theoretical Study

NMR, IR, conformation and hydrogen bonding

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