McLafferty rearrangement
The McLafferty rearrangement is an organic reaction seen in mass spectrometry. A mass spectrometer breaks apart the molecule being studied. The molecule breaks apart in consistent ways that chemists can predict. Most of the time, a carbon-carbon bond breaks and the atoms do not jump across the break between the fragments. The McLafferty rearrangement is an example of a hydrogen atom jumping to the other fragment as a part of the process of the bond breaking. It happens in an organic molecule containing a keto-group.
The reaction[change | change source]
The American chemist Fred McLafferty was the first to describe the reaction in 1959.[1][2][3]
An example of the McLafferty rearrangement
The keto-group undergoes β-cleavage, with the gain of the γ-hydrogen atom. This rearrangement may take place by a radical or ionic mechanism.
Related pages[change | change source]
References[change | change source]
- ↑ F. W. McLafferty (1959). "Mass Spectrometric Analysis. Molecular Rearrangements". Anal. Chem. 31 (1): 82–87. doi:10.1021/ac60145a015.
- ↑ 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. S2CID 42341600.
- ↑ 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. S2CID 22883437.
Further reading[change | change source]
- International Union of Pure and Applied Chemistry. "McLafferty rearrangement". Compendium of Chemical Terminology Internet edition.