アニリドの側鎖同族体およびフェニル置換誘導体のマススペクトル

概要

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The mass spectra of anilides represented general formula o- or p-ClC6H4NHCOR (R=H,CH3~C3H7, i-C3H7) and substituted formanilides (R=H) and acetanilides (R=CH3) were measured to determine the effect of R and substituent on anilide fragmentation.The mass spectra of anilides of R = CH3~C3H7, i-C3H7 independent of length of R indicated almost the same fragmentation, qualitatively and quantitatively except for the -CO-R bond simple cleavage in R=C2H5, C3H7, i-C3H7. 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, NO2, NH2, CH3, C2H5) produced specific fragment ions but almost all p- and m-isomeres didnt. 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.
日本質量分析学会の論文