Vibrational Circular Dichroism study of chiral food additives: γ-valero- and γ-caprolactone

Valera, Manuel; Jaraices, R. Casas; Montejo, Manuel; Ortega, Pilar Gema Rodríguez

doi:10.1016/j.saa.2020.119140

Cited by 5 publications

(2 citation statements)

References 40 publications

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“…This value is only barely outside of the error bar of the previously reported ionization onset at 9.98 ± 0.05 eV . As recently pointed out by Sánchez Valera et al in a vibrational circular dichroism study, GVL is chiral because of the environment of the γ-carbon. It also has two comparably stable conformers.…”

Section: Resultssupporting

confidence: 55%

Photoionization of Two Potential Biofuel Additives: γ-Valerolactone and Methyl Butyrate

et al. 2021

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The photoionization of two potential biofuel additives, γ-valerolactone (GVL, C 5 H 8 O 2 ) and methyl butyrate (MB, C 5 H 10 O 2 ) has been studied by imaging photoelectron photoion coincidence spectroscopy (iPEPICO) at the VUV beamline of the Swiss Light Source (SLS). The vibrational fine structure in the photoelectron spectrum is compared with a Franck−Condon simulation for the electronic ground-state band of the GVL cation. In the lowest energy dissociative photoionization channel of GVL, CO 2 is lost, resulting in a 1-butene fragment ion with a 0 K appearance energy of E 0 = 10.35 ± 0.01 eV. A newly calculated 1-butene ionization energy of 9.595 ± 0.015 eV establishes the reverse barrier height to CO 2 loss as 66.6 ± 4.3 kJ mol −1 . Methyl butyrate cations undergo McLafferty rearrangement, which explains the missing ion signal at the computed adiabatic ionization energy of 9.25 eV. After H transfer, ethylene is lost in the lowest energy dissociation channel to yield the methyl acetate enol ion at E 0 = 10.24 ± 0.04 eV. This value connects the energetics of methyl butyrate with that of methyl acetate enol ion, which is established atParallel to ethylene loss, methyl loss is also observed from the enol tautomer of the parent ion. Both samples exhibit low-energy nonstatistical dissociative ionization channels. In GVL, the methyl-loss abundance rises quickly but levels off suddenly in the energy range of the first electronically excited states, indicating nonstatistical competition between CH 3 and CO 2 loss. In MB, the major parallel dissociation channel is the loss of a methoxy radical. Calculations indicate that McLafferty rearrangement is inhibited on the excited-state surface. Indeed, breakdown curve modeling of this and a sequential CO-loss channel confirms a second statistical regime in dissociative photoionization, decoupled from ethylene loss.

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Section: Resultssupporting

confidence: 55%

Photoionization of Two Potential Biofuel Additives: γ-Valerolactone and Methyl Butyrate

et al. 2021

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“…The discrimination of chiral compounds such as amino acids (except glycine), saccharides, and chiral drugs is an eternal topic since the discovery of chirality in the early 19th century, especially with the happening of the thalidomide event in the middle of the 20th century. − Among the strategies proposed for chiral discrimination such as colorimetry, spectrometry, , chromatography, , and electrochemical methods, , electrochemical sensors are especially attractive because of their low cost, high sensitivity, and simple operation. − However, relatively low reproducibility is generally encountered by electrochemical methods, and thus, the reliability of electrochemical chiral discrimination is significantly reduced, especially when the target enantiomers produce the electrochemical signals (currents, potential, and impedance) at similar intensities. Therefore, it is a great challenge to improve the reliability of the single-mode (electrochemistry) chiral analysis.…”

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confidence: 99%

Highly Reliable Chiral Discrimination of Tryptophan Enantiomers through Two Different Modes: Electrochemistry and Temperature

Jing

Wen

et al. 2023

Anal. Chem.

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γ-Valerolactone and Other Relevant Lactones

Mika,

Árvai

2024

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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Vibrational Circular Dichroism study of chiral food additives: γ-valero- and γ-caprolactone

Cited by 5 publications

References 40 publications

Photoionization of Two Potential Biofuel Additives: γ-Valerolactone and Methyl Butyrate

Photoionization of Two Potential Biofuel Additives: γ-Valerolactone and Methyl Butyrate

Highly Reliable Chiral Discrimination of Tryptophan Enantiomers through Two Different Modes: Electrochemistry and Temperature

γ-Valerolactone and Other Relevant Lactones

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