Quinoxalinol derivatives of aliphatic 2-oxocarboxylic acids. Infrared and mass spectra of theO-trimethylsilylated compounds

Langenbeck, U.; Möhring, H.; Hinney, B.; Spiteller, M

doi:10.1002/bms.1200040402

Cited by 33 publications

(7 citation statements)

References 23 publications

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“…The spectrum of the TMS/quinoxalinol derivative of 2‐oxohexanedioic acid ( 221 ) contains a minor ion at m/z 289 ( nc , Scheme ) that was proposed to arise by a McLafferty rearrangement from a precursor at m/z 333 that had lost CH 3 • from a TMS group of the molecular ion followed by C 2 H 4 (Langenbeck et al, ). A detailed mechanism was not proposed.…”

Section: Trimethylsilyl Derivativesmentioning

confidence: 99%

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Harvey

Vouros

2019

Mass Spectrometry Reviews

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This review describes the mass spectral fragmentation of trimethylsilyl (TMS) and related alkylsilyl derivatives used for preparing samples for analysis, mainly by combined gas chromatography and mass spectrometry (GC/MS). The review is divided into three sections. The first section is concerned with the TMS derivatives themselves and describes fragmentation of derivatized alcohols, thiols, amines, ketones, carboxylic acids and bifunctional compounds such as hydroxy‐ and amino‐acids, halo acids and hydroxy ethers. More complex compounds such as glycerides, sphingolipids, carbohydrates, organic phosphates, phosphonates, steroids, vitamin D, cannabinoids, and prostaglandins are discussed next. The second section describes intermolecular reactions of siliconium ions such as the TMS cation and the third section discusses other alkylsilyl derivatives. Among these latter compounds are di‐ and trialkyl‐silyl derivatives, various substituted‐alkyldimethylsilyl derivatives such as the tert‐butyldimethylsilyl ethers, cyclic silyl derivatives, alkoxysilyl derivatives, and 3‐pyridylmethyldimethylsilyl esters used for double bond location in fatty acid spectra. © 2019 Wiley Periodicals, Inc. Mass Spec Rev 0000:1–107, 2019

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Section: Trimethylsilyl Derivativesmentioning

confidence: 99%

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Harvey

Vouros

2019

Mass Spectrometry Reviews

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“…Mass spectrometry (MS) was carried out on a Finnigan model 4000 GC-MS combination [18]. Alternatively, acid ether extracts of urine were esterified with diazomethane and analyzed by GC and GC-MS [20].…”

Section: Identification and Quantitation Of Metabolites In Body Fluidsmentioning

confidence: 99%

A familial progressive neurodegenerative disease with 2-oxoglutaric aciduria

et al. 1982

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A boy and a girl born to a consanguineous Tunisian couple are suffering from a slowly progressive nervous disorder. Initially they both had normal psychomotor development with acquisition of gait and speech. First symptoms in the boy were athetoid movements during the second year of life. He later lost all motor and language skills and developed muscular rigidity and intention tremor. At the age of five years, he was completely bedridden while he appeared mentally much less affected. His younger sister followed a similar course. The major specific abnormality detected was a strikingly elevated excretion of 2-oxoglutaric acid, which was identified by gas liquid chromatography, mass spectrometry, and enzymatic analysis. 2-oxoglutarate dehydrogenase activity in homogenates of cultured skin fibroblasts was reduced to about 25% of control values in both children. Although the pathogenetic mechanisms leading to brain damage remain obscure, the finding strongly suggest an autosomal recessive neurometabolic disease with predominant involvement of the extrapyramidal system.

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“…2. In the naphthalene part of the molecule, the bond distances are alternately short and long, with values varying between 1.352 (6) and 1.433(6) A. Such an occurrence is not unusual.…”

Section: Molecular Conformationmentioning

confidence: 92%

“…They mentioned having obtained evidence from nmr and ir data that the condensation products are amides and that further silylation occurs on the nitrogen atom. Later reports by Frigerio et al ( 5 ) and Langenbeck et al (6) using FT-IR and mass spectrometry seem to indicate that silylation of the "quinoxalinol" derivatives takes place at the oxygen. Langenbeck suggested that an enol-keto equilibrium in solution could account for the results.…”

Section: Introductionmentioning

confidence: 96%