Electron ionization-induced fragmentation patterns of the series of N-(alkoxymethyl)acetanilides and related formanilides and benzanilides have been studied. The main fragmentation reaction observed for all compounds studied is the loss of an alkyl radical from the N-alkoxymethyl group leading to the appropriate protonated N-acylformanilide derivatives. This reaction is accompanied by unusually high kinetic energy release. Other important fragmentations common for majority of the compounds studied are (i) loss of an aldehyde molecule derived from an alkoxyl group yielding an appropriate N-acyl-N-methylaniline, (ii) elimination of a C(n)H(2n)O(2) fragment derived from N-alkoxymethyl group and carbonyl group oxygen atom and (iii) formation of N-methyleneaniline radical cation.
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