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Eur. J. Mass Spectrom. DOI: 10.1255/ejms.592

Derivatization in mass spectrometry. 3. Alkylation(arylation)

John M. Halket
Drug Control Centre, King's College London, Franklin-Wilkins Building, Stamford Street, London SE1 9NN, UK. E-mail:
Vladimir G. Zaikin
Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Moscow, Russia. E-mail:

ABSTRACT:
The review is devoted to alkylation(arylation) as a widely employed derivatization procedure for the protection of OH (carboxylic acids, phosphoric acids, sulphonic acids, alcohols, polyols, phenols, enols), SH (thiols) and NH (amines, amides) groups in order to increase volatility, to improve the chromatographic and, if possible, mass spectral properties of derivatives. Chemical aspects of derivatization and various alkylation(arylation) reagents and reaction procedures are described. Specific mass spectral (EI, CI) features of derivatives helpful in identification, structure elucidation, profiling and quantitative determination of the above-mentioned polar compounds by GC/MS and HPLC/MS are discussed. Some common analytical applications of the procedures in organic chemistry, clinical chemistry, environmental etc. are briefly summarized.

Keywords: alcohols, alkylation, alkylating agents, alkyl halides, arylation, diazomethane, derivatives, derivatization, phenols, thiols, amines, amides, carboxylic acids, chemical warfare agents, phosphonic acids, phosphoric acids, sulphonic acids, pentafluorobenzyl derivatives, picolinyl esters, trimethylsilyldiazomethane, electron ionization, chemical ionization, gas chromatography/mass spectrometry, high performance liquid chromatography/mass spectrometry

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