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Mass spectrometric investigation of diphenylacetylene (tolane)
Author(s) -
Srzić Dunja,
Žinić Mladen,
Meić Zlatko
Publication year - 1990
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.1290040807
Subject(s) - diphenylacetylene , chemistry , fragmentation (computing) , radical , mass spectrum , ion , electron ionization , mass spectrometry , deuterium , hydrogen , analytical chemistry (journal) , crystallography , photochemistry , ionization , computational chemistry , organic chemistry , atomic physics , chromatography , physics , computer science , catalysis , operating system
The electron‐ionization induced fragmentation of diphenylacetylene and its d 1 , d 2 , d 5 and d 10 analogues has been studied by mass spectrometry. The main fragment ions found in the mass spectrum of diphenylacetylene are due to the loss of two hydrogen radicals in a stepwise process and expulsion of C 2 H 2 from the molecular ion in parallel fragmentation pathways producing the fragment ions at m/z 176 and m/z 152, respectively, the latter having possibly a biphenylene radical cation structure. Knowing the actual composition of deuterated derivatives, and the fragmentation pattern of diphenylacetylene, the distribution of the label in these ions was calculated under the assumption that this distribution is statistical. The final results were compared with the experimentally observed spectra of deuterated compounds. This comparison favours the assumption of hydrogen randomization prior to m/z 176 and m/z 152 formation. In contrast to the loss of hydrogen radicals and of C 2 H 2 , the formation of m/z 139, 126 and 102 does not involve any major hydrogen scrambling between the phenyl rings.

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