Generation of alkoxide anions from a series of aliphatic diols and alcohols and their ion-molecule reactions with carbon dioxide in the gas phase

Eur. J. Mass Spectrom. 12, 19–24 (2006)
DOI: 10.1255/ejms.791

Generation of alkoxide anions from a series of aliphatic diols and alcohols and their ion-molecule reactions with carbon dioxide in the gas phase

M. Ravi Kumar, S. Prabhakar, T. Jagadeshwar Reddy and M. Vairamani^*
National Center for Mass Spectrometry, Indian Institute of Chemical Technology, Hyderabad, India-500 007

ABSTRACT:

Alkoxide anions, [M – H]^– from a series of aliphatic diols and alcohols are generated in the source under negative ion electrospray ionisation conditions by cone-voltage fragmentation of the corresponding [M + F]^– ions. The collision-induced dissociation (CID) spectra of [M – H]^– ions consist of [M – H2H]^– ions, in addition to the other characteristic fragment ions, and the relative abundance of [M – H2H^– ions among the series of diols varies as a function of chain length that could be explained based on their stabilities through intramolecular hydrogen bonding. The reactivity of alkoxide anions is studied through ion–molecule reactions with CO₂ in the collision cell of a triple quadrupole mass spectrometer. All the alkoxide anions reacted with CO₂ and formed corresponding carbonate anions, [M – H + CO₂]^– ions. The reactivity of alkoxide anions within the series of diols also reflected the stability of their [M – H]^– ions

Keywords: negative ESI, aliphatic diols, halide ion attachment, alkoxide ion, ion molecule reactions

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