Cyclic Boronates as Derivatives for the Gas Chromatography—Mass Spectrometry of Bifunctional Organic Compounds

Kossa, Walter C.

doi:10.1007/978-1-4615-9194-8_2

Cited by 5 publications

(1 citation statement)

References 116 publications

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“…Cyclic alkyl (alkyl = methyl, butyl, tert-butyl)-, cyclohexyl-and phenylboronates are a widely distributed class of derivatives for polyfunctional compounds. [20][21][22][23] They are usually formed from compounds containing two OH, NH and/ or COOH groups in the 1,2-, 1,3-or even 1,4-positions; the six-membered rings being more stable than five-or sevenmembered ones:…”

Section: Cyclic Boronatesmentioning

confidence: 99%

Derivatization in Mass Spectrometry—4. Formation of Cyclic Derivatives

Заикин

Halket

2004

Eur J Mass Spectrom (Chichester)

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This fourth in a series of reviews describes a further common derivatization approach, namely, the formation of cyclic derivatives (cyclic acetals and ketals, boronates, siliconides, carbonates and other miscellaneous derivatives) that can be used to increase volatility and to improve chromatographic and, if possible, the mass spectral properties of various di- and polyfunctional compounds. Some chemical aspects of this type of derivatization are briefly discussed. Characteristic mass spectral features of various cyclic derivatives that are helpful in the structure determination, profiling and quantitation of multifunctional organic compounds are presented. Some recent analytical applications of mass spectrometry in conjunction with preliminary cyclic derivative formation are given.

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Section: Cyclic Boronatesmentioning

confidence: 99%

Derivatization in Mass Spectrometry—4. Formation of Cyclic Derivatives

Заикин

Halket

2004

Eur J Mass Spectrom (Chichester)

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Analysis of the linkage positions and isomers of monosaccharide units in oligosaccharides by negativ secondary ion mass spectrometry in combination with the stereoselective reaction with substituted boronic acid

Lin

Fang

1993

Chin. J. Chem.

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The negative secondary ion mass spectrometry, in combination with the stereoselective derivatizations with substituted boronic acid RB(OH)2, was used in the analysis of fourteen oligosaccharides. The mass spectra of the derivatives provide information on their linkage positions and isomerism of the individual monosacaccharide units. The results indicated that among the derivatives of the oligosaccharides analyzed, those with 1–4 and 1–6 linkages all presented the ion peaks at m/z 287, sometimes one more peak at m/z 449. Furthermore, a relationship was found between the linkage positions and the intensity orders of the derivative ions. Finally, the derivatives of the disaccharides with a galactose presented an intense ion peak at m/z 347, and those of oligosaccharides with 1–6 linkage to a galactose at terminal presented the ion at m/z 317. In the case of oligosaccharides with a fructose residue, characteristic ion of m/z 155 was produced. The conditions of stereoselective derivatizations and mass spectrometry were studied, in order to obtain a better reproducibility of the mass spectra.

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Derivatization and mass spectrometric investigations of substituted benzeneboronic acids. The use of linked scanning during gas chromatography mass spectrometry

Longstaff

Rose

1982

Org. Mass Spectrom.

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Substituted benzeneboronic acids are important intermediates in the synthesis of support matrices for Srsnity chromatography but their analysis by mass spectrometry is hindered by thermal reactions in the ion source. A simple derivatization with 1,2-or 1,3-diols removes this daculty and imparts sufficient volatility for application of gas chromatography/mass spectrometry. The mass spectra of the resulting boronate esters are discussed with reference to high resolution measurements, isotope labelling studies and observation of metastable ions. ortho Substhents are shown to interact strongly during fragmentation. Linked scanning at constant BIE was used to characterize fragmentation pathways and the compatibility of linked scanning and GC/MS is reported.

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Cyclic Boronates as Derivatives for the Gas Chromatography—Mass Spectrometry of Bifunctional Organic Compounds

Cited by 5 publications

References 116 publications

Derivatization in Mass Spectrometry—4. Formation of Cyclic Derivatives

Derivatization in Mass Spectrometry—4. Formation of Cyclic Derivatives

Analysis of the linkage positions and isomers of monosaccharide units in oligosaccharides by negativ secondary ion mass spectrometry in combination with the stereoselective reaction with substituted boronic acid

Derivatization and mass spectrometric investigations of substituted benzeneboronic acids. The use of linked scanning during gas chromatography mass spectrometry

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