Chromatographic and chromatospectral characteristic of dicarboxylic acid monoesters

Зенкевич, И. Г.; Fakhretdinova, Lilia N.

doi:10.1134/s106193481612011x

Cited by 11 publications

(5 citation statements)

References 18 publications

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“…3h was purchased and used directly upon receipt. 3a , 3b , 3c , 3d , 3e , 3g , 3i , 3k , 3l , and 3q were prepared according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Zwitterion-Catalyzed Isomerization of Maleic to Fumaric Acid Diesters

Lam

Yeung

2020

J. Org. Chem.

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Fumaric acid diesters are important building blocks for organic synthesis. A class of zwitterionic organocatalysts based on an amide anion/iminium cation charge pair were found to be effective in catalyzing the isomerization of maleic acid diesters to give fumaric acid diesters. Comparison of the performance of different zwitterionic organocatalysts toward the reaction revealed that nonclassical hydrogen bonding was involved in the stabilization of the Michael adduct intermediate.

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“…3h was purchased and used directly upon receipt. 3a , 3b , 3c , 3d , 3e , 3g , 3i , 3k , 3l , and 3q were prepared according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Zwitterion-Catalyzed Isomerization of Maleic to Fumaric Acid Diesters

Lam

Yeung

2020

J. Org. Chem.

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“…Because of the wide range of i RI values, their averaging is senseless. However, the retention indices of monoand di-n-alkyl phthalates correlate well with each other [8], which can be considered as a proof of their correctness for both series. The retention indices of din-alkyl phthalates and their homologous increments are given in Table 1 in comparison with some of the physicochemical characteristics of these compounds discussed below.…”

Section: Anomalies Of Homologous Increments Of Gas Chromatographic Retention Indices Of Dialkyl Phthalates and Their Interpretationmentioning

confidence: 62%

“…The parameters for GC-MS identification of monoalkyl benzene-1,2-dicarboxylates (monoalkyl phthalates) were considered in [8,9]. The chromatographic characteristics of this series have no anomalies: the i RI values of n-alkyl phthalates are well reproducible (the average value ± the standard deviation is 341 ± 14); if the alkyl fragment contains one branch, these estimates naturally decrease to 255 ± 25.…”

Section: Anomalies Of Homologous Increments Of Gas Chromatographic Retention Indices Of Dialkyl Phthalates and Their Interpretationmentioning

confidence: 99%

“…The data for monoalkyl phthalates were compared with the analogous characteristics of their closest structural analogs-dialkyl phthalates (dialkyl benzene-1,2-dicarboxylate) [8,9]. At the same time, it was unexpectedly found that the i RI values of di-nalkyl phthalates were not reproducible and significantly decreased at increased number of carbon atoms in n-alkyl fragments, from +125 (dimethyl phthalate) to -33 (didecyl phthalate), i.e., by ~160 index units.…”

Section: Anomalies Of Homologous Increments Of Gas Chromatographic Retention Indices Of Dialkyl Phthalates and Their Interpretationmentioning

confidence: 99%

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Determination of Anomalies of Gas Chromatographic Retention Indices for Homologs Based on Their Homologous Increments

Зенкевич

2021

Russ. J. Phys. Chem.

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“…Thus, the similarity of the mass spectra of dialkyl and trialkyl phosphites with the same alkyl fragments R gives rise to a problem of distinguishing the compounds of these series. The same problem exists for other complete esters of polyfunctional acids and corresponding partial (acidic) esters, e.g., dialkyl and monoalkyl phthalates …”

Section: Introductionmentioning

confidence: 94%

Comparative gas chromatographic/mass spectrometric characterization of di‐ and trialkyl phosphites

Зенкевич

Nosova

2019

Rapid Comm Mass Spectrometry

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Rationale: Homologous series of alkyl esters of phosphorus-containing acids, namely, dialkyl phosphonates (synonym: dialkyl phosphites) and trialkyl phosphites, were characterized by electron ionization (EI) mass spectra and gas chromatographic retention indices (GC RI) on semi-standard non-polar stationary phases. It is confirmed that GC/MS characterization of any sets of homologues should not be restricted to independent registration of these analytical parameters. Their joint processing in the form of so-called homologous increments of GC RIs means, firstly, a novel way of evaluating the chromatographic polarity of analytes and, secondly, a new algorithm for the prediction of their molecular weights if no peaks of molecular ions are registered in the mass spectra. Methods:A standard GC/MS technique, including determination of GC RIs on semi-standard nonpolar stationary phases in temperature-programmed regime and electron ionization (EI) mass spectra was used.Results: A total of 31 dialkyl phosphonate homologues and 37 trialkyl phosphite homologues were characterized by EI mass spectra and GC RIs for the first time.Joint processing of these analytical parameters allows the calculation of so-called homologous increments of GC RIs, which are useful parameters for evaluating the chromatographic polarity of analytes and predicting their molecular weights.Conclusions: GC/MS characterization of any sets of homologues should not be restricted to independent registration of the mass spectra and chromatographic retention parameters. Their joint processing in the form of so-called homologous increments of GC retention indices means, firstly, a novel way of evaluating the chromatographic polarity of analytes and, secondly, a new algorithm for predicting their molecular weights.

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Chromatographic and chromatospectral characteristic of dicarboxylic acid monoesters

Cited by 11 publications

References 18 publications

Zwitterion-Catalyzed Isomerization of Maleic to Fumaric Acid Diesters

Zwitterion-Catalyzed Isomerization of Maleic to Fumaric Acid Diesters

Determination of Anomalies of Gas Chromatographic Retention Indices for Homologs Based on Their Homologous Increments

Comparative gas chromatographic/mass spectrometric characterization of di‐ and trialkyl phosphites

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