McLafferty rearrangement

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The McLafferty rearrangement is a reaction observed in mass spectrometry during the fragmentation or dissociation of organic molecules. It is sometimes found that a molecule containing a keto-group undergoes β-cleavage, with the gain of the γ-hydrogen atom, as first reported by Anthony Nicholson working in the Division of Chemical Physics at the CSIRO in Australia.[1] This rearrangement may take place by a radical or ionic mechanism.

The reaction[edit]

A description of the reaction was later published by the American chemist Fred McLafferty in 1959 leading to his name being associated with the process.[2][3][4]

See also[edit]


  1. ^ A. J. C. Nicholson (1954). "The photochemical decomposition of the aliphatic methyl ketones". Trans. Faraday Soc. 50: 1067–1073. doi:10.1039/TF9545001067.
  2. ^ F. W. McLafferty (1959). "Mass Spectrometric Analysis. Molecular Rearrangements". Anal. Chem. 31 (1): 82–87. doi:10.1021/ac60145a015.
  3. ^ Gross ML (2004). "Focus in honor of Fred McLafferty, 2003 Distinguished Contribution awardee, for the discovery of the "McLafferty Rearrangement"". J. Am. Soc. Mass Spectrom. 15 (7): 951–5. doi:10.1016/j.jasms.2004.05.009. PMID 15234352.
  4. ^ Nibbering NM (2004). "The McLafferty rearrangement: a personal recollection". J. Am. Soc. Mass Spectrom. 15 (7): 956–8. doi:10.1016/j.jasms.2004.04.025. PMID 15234353.

Further reading[edit]

External links[edit]