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Electron Impact Mass Spectra of Carbonyl Hydrazones of o-Aminoaryl Ketones

โœ Scribed by Antigoni Kotali


Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
130 KB
Volume
10
Category
Article
ISSN
0951-4198

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โœฆ Synopsis


The title compounds are prepared from the reaction of o-aminoaryl ketones with hydrazides. Their electron impact mass spectra are reported. In addition to the molecular ion, characteristic peaks appear at values corresponding to the [M -NHJ, [M -NHCOX]' and [M -COX]' ions.

Recently, we reported the synthesis of 0-aminoaryl ketone acylhydrazones 1 along with their oxidative cyclization to 2acylaminoindazoles, on treatment with lead(1V)acetate.

Continuing our interest in the nitrogen derivatives of carbonyl compounds and especially in their behaviour in mass spectrometry, we now report their electron-impact mass spectra.


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Fragmentation pathways of the title compounds under electron impact were compared to those of their (1aryl)substituted analogs reported earlier. The main fragmentation route of the M ร ions is the sulphamide N-S bond cleavage leading to [M ร€ ArSO 2 ] ions. No loss of the alkyl substituents from the

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Table 1. The EI mass spectra, showing peaks of >5% relative abundance (RA), of compounds 1-10, using 70 eV electrons Compound m/z (% RA) 1 315(M, 55) 314(10) 161(10) 160(89) 159(13) 107(12) 106(100) 105(11) 104(9) 91(33) 77(22) 65(15) a 2 345(M, 4) 316(7) 315(19) 314(100) 190(11) 175(7) 172(5) 160(1

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Fragmentation pathways of the title compounds were studied using accurate mass measurements and collision-induced dissociation spectra. Substituents in the ortho position of the aryl group at the pyrimidine ring were found to play a special role in the electron impact (EI) induced fragmentation of t