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The [M−H−CO2]− anion from glycyl glycine undergoes rearrangement in the gas phase

✍ Scribed by Michelle L. Styles; Richard A. J. O’Hair

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
188 KB
Volume
12
Category
Article
ISSN
0951-4198

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✦ Synopsis

The [MÀHÀCO 2 ] À anion derived from collision induced loss of CO 2 from the [MÀH] À ion of glycyl glycine has been examined using various tandem mass spectrometry (MS/MS) experiments. Using 15 N isotopically labelled glycyl glycine, these MS/MS experiments reveal that the initially formed carbanion [H 2 NCH 2 C(O)NHCH 2 ] À (A) undergoes rearrangement to the nitrogen anion [HNCH 2 C(O)NHCH 3 ] À (B). The latter ion is responsible for the subsequent fragmentation reactions. In addition, high level ab initio calculations (at the MP2/6-31G * level of theory) have been carried out on the rearrangement of A to B, which reveal that this intramolecular rearrangement process proceeds via a six centred transition state with a modest activation energy (11.1 kcal mol À1 ) and is overall exothermic by 3.2 kcal mol À1 thereby favouring the formation of the product B.

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