Chemical derivatization for electrospray ionization mass spectrometry. 1. Alkyl halides, alcohols, phenols, thiols, and amines

Journal Article · Fri Apr 15 00:00:00 EDT 1994 · Analytical Chemistry (Washington); (United States)

DOI:https://doi.org/10.1021/ac00080a016· OSTI ID:7069816

Quirke, J M.E.; Adams, C L; Van Berkel, G J ^[1]

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1. Oak Ridge National Lab., TN (United States)

Derivatization strategies and specific derivatization reactions for conversion of simple alkyl halides, alcohols, phenols, thiols, and amines to ionic or solution-ionizable derivatives, that is [open quotes]electrospray active[close quotes] (ES-active) forms of the analyte, are presented. Use of these reactions allows detection of analytes among those listed that are not normally amenable to analysis by electrospray ionization mass spectrometry (ES-MS). In addition, these reactions provide for analysis specificity and flexibility through functional group specific derivatization and through the formation of derivatives that can be detected in positive ion or in negative ion mode. For a few of the functional groups, amphoteric derivatives are formed that can be analyzed in either positive or negative ion modes. General synthetic strategies for transformation of members of these five compound classes to ES-active species are presented along with illustrative examples of suitable derivatives. Selected derivatives were prepared using model compounds and the ES mass spectra obtained for these derivatives are discussed. The analytical utility of derivatization for ES-MS analysis is illustrated in three experiments: (1) specific detection of the major secondary alcohol in oil of peppermint, (2) selective detection of phenols within a synthetic mixture of phenols, and (3) identification of the medicinal amines within a commercially available cold medication as primary, secondary or tertiary. 65 refs., 3 figs., 3 tabs.

• DOE Contract Number: AC05-84OR21400
• OSTI ID: 7069816
• Journal Information: Analytical Chemistry (Washington); (United States), Journal Name: Analytical Chemistry (Washington); (United States) Vol. 66:8; ISSN 0003-2700; ISSN ANCHAM
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400102 -- Chemical & Spectral Procedures
400201* -- Chemical & Physicochemical Properties
ALCOHOLS
AMINES
AROMATICS
CHEMICAL REACTIONS
COMPILED DATA
DATA
DERIVATIZATION
DRUGS
ESSENTIAL OILS
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROXY COMPOUNDS
INFORMATION
IONIZATION
MASS SPECTROSCOPY
NUMERICAL DATA
OILS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OTHER ORGANIC COMPOUNDS
PHENOLS
SPECTROSCOPY
THIOLS