The mass spectra of anilides represented general formula
o- or
p-ClC
6H
4NHCOR (R=H,CH
3~C
3H
7,
i-C
3H
7) and substituted formanilides (R=H) and acetanilides (R=CH
3) were measured to determine the effect of R and substituent on anilide fragmentation.
The mass spectra of anilides of R = CH
3~C
3H
7,
i-C
3H
7 independent of length of R indicated almost the same fragmentation, qualitatively and quantitatively except for the -CO-R bond simple cleavage in R=C
2H
5, C
3H
7,
i-C
3H
7. But, those of formanilides were characterized by fairly strong M
+·, strong fragments produced from [M-ketene]
+·, prominent
o-effect ([M-Cl]
+) and weak fragments produced through the -NH-CO- bond cleavage involving ketene elimination, and little HC≡O
+.
In investigations of mono substituted formanilides and acetanilides, it was found that
o-isomeres (Cl, NO
2, NH
2, CH
3, C
2H
5) produced specific fragment ions but almost all
p- and
m-isomeres didn't. This
o-effect was stronger in formanilides than in acetanilides and [M-OH]
+ ions from
o-alkyl isomeres were recognized only in formanilides.
It was concluded that three isomeres (
o-,
m-, or
p-) in nitroformanilide, methoxy-formanilide, aminoformanilide and aminoacetanilide could be identified.
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