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The unimolecular fragmentation of steroidal amides under electron impact. The role of intermediary ion-neutral complexes

✍ Scribed by Pierre Longevialle; Guy Bouchoux And; Yannik Hoppilliard

Publisher: John Wiley and Sons
Year: 1989
Tongue: English
Weight: 535 KB
Volume: 24
Category: Article
ISSN: 1076-5174
DOI: 10.1002/oms.1210241013

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✦ Synopsis

The neutral fragment produced in the main decomposition process of Iamido steroids after electron impact is shown, by thennochemical arguments, to have the amide structure rather than enolamide as would be expected from a simple McLafferty rearrangement. It is proposed that the enolamide to amide tautomerization takes place during the decomposition process involving ion-neutral complexes, and is responsible for the lack of regioselectivity in the origin of the hydrogen transferred. An energy barrier of unknown origin is shown to exist in the formation of the accompanying [amide + H J ' ion.

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