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Mass spectral fragmentation pathways in cyclic difluoramino and nitro compounds
Author(s) -
Zhang Jun,
Oxley Jimmie,
Smith James,
Bedford Clifford,
Chapman Robert
Publication year - 2000
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/1096-9888(200007)35:7<841::aid-jms8>3.0.co;2-0
Subject(s) - chemistry , fragmentation (computing) , nitro , mass spectrum , mass spectrometry , stereochemistry , computational chemistry , organic chemistry , chromatography , alkyl , computer science , operating system
The recently synthesized compounds 4,4‐bis(difluoramino)‐1‐nitropiperidine (I), 1,4,4‐trinitropiperidine (II), 1,1,4,4‐tetranitrocyclohexane (III), 1,1,4,4‐tetrakis(difluoramino)cyclohexane (IV) and 3,3,7,7‐tetrakis(difluora‐mino)octahydro‐1,5‐dinitro‐1,5‐diazocine (HNFX, V) are being considered as potential energetic materials. The mass spectra of these compounds were studied using electron ionization (EI) mass spectrometry. A collision‐induced dissociation (CID) study of the major EI peaks was carried out using a Finnigan TSQ 700 tandem mass spectrometer. The mass fragmentation pathways are constructed and discussed. The decomposition of HNFX (V), under EI, appeared to parallel the thermal decomposition of nitramines where N—NO 2 cleavage is often the first step. However, the two nitramines with a six‐membered ring structure (I and II) underwent initial loss of a geminal substituent; loss of a nitramine nitro group was the secondary step. The two cyclohexane structures (III and IV) showed similar initial fragmentation pathways, featuring successive losses of nitro or difluoramino groups. Copyright © 2000 John Wiley & Sons, Ltd.