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Amidine mass spectral fragmentation patterns

✍ Scribed by James Barker; Michael Jones; Melvyn Kilner

Publisher
John Wiley and Sons
Year
1985
Tongue
English
Weight
311 KB
Volume
20
Category
Article
ISSN
1076-5174

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✦ Synopsis

Electron impact mass spectrometry of a range of amidines (R'NC(R)NHR') including formamidines, acetamidines, benzamidines and tert-butylamidine, has been undertaken, and comparisons made of the fragmentation pathways followed by the different families of compounds. Fragmentation of all the molecular ions is characterized by skeletal cabon-nitrogen bond cleavage to form [R'NCR]' and [R'NH]' fragments, both of which are observed. For formamidines (R=H), the positive charge remains with the [R'NH]' fragment which leads to the base peak at m/z93 corresponding to [R'NH,]". In contrast, for acetamidines and bemamidines the charge prefers to remain with the [R'NCR]+ fragment which gives the base peak for these compounds. The spectra of unsubstituted amidines (HNC(R)NH,) are characterized by cleavage of the carbon substituent from the NCN skeleton, [CNzH3]+ (rn/z43) k i n g produced in all cases.

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The electron impact mass spectra of several gem-bisamides are studied. The dominant peaks in the spectra of alkylidene and arylidene bisalkylamides are formed by the cleavage of the C -N bond of the amido group with charge retention on the nitrogen atom. This fragmentation, followed by the loss of a