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Electrophilic aromatic substitution under chemical ionization conditions. Methylamine and ammonia as reagent gases
Author(s) -
Luijten W. C. M. M.,
Onkenhout W.,
van Thuijl J.
Publication year - 1980
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210150702
Subject(s) - chemistry , methylamine , nitrobenzene , reagent , adduct , ammonia , medicinal chemistry , electrophilic substitution , substitution reaction , inorganic chemistry , ion , chemical ionization , ionization , organic chemistry , catalysis
For compounds C 6 H 5 X (XCl, Br, I) under chemical ionization conditions, methylamine causes ipso substitution of X by [NH 2 CH 3 ] + and by [NH 2 ] + ˙. C 6 H 5 F is less reactive; it gives some [C 6 H 5 NH 2 ] + ˙. Nitrobenzene gives an adduct ion [M+CH 3 NH 3 ] + , a reduction product ion [C 6 H 5 NO 2 ] + ˙, and an ion at m / z 93, probably a substitution product [C 6 H 5 NH 2 ] + ˙, but no [C 6 H 5 NH 2 CH 3 ] + . It is also shown that the ion m / z 94, formed from nitrobenzene with ammonia as reagent gas, is a substitution product rather than a reduction product ion. Carbonyl compounds C 6 H 5 . CO. X give adduct ions and some substitution, mainly [C 6 H 5 NH 2 ] + ˙.