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Mass spectral studies of naphthoflavones
Author(s) -
Guidugli F. H.,
Kavka J.,
Garibay M. E.,
Santillan R. L.,
JosephNathan P.
Publication year - 1987
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.1210220802
Subject(s) - tropolone , deuterium , labelling , metastability , chemistry , ion , cleavage (geology) , kinetic isotope effect , residue (chemistry) , isotope , stereochemistry , photochemistry , computational chemistry , organic chemistry , atomic physics , materials science , biochemistry , physics , quantum mechanics , fracture (geology) , composite material
The electron impact induced fragmentations of the five possible naphthoflavones have been studied with the aid of low‐ and high‐resolution measurements, metastable decompositions and isotope labelling using either deuterium or carbon‐13 atoms. All compounds show both the direct expulsion of a CO residue from the carbonyl group and the retro Diels–Alder cleavage. The abundant [M–H] + ion has been formulated as the substituted β‐tropolone species, which, in the case of β‐naphthoflavone, is in competition with a pentacyclic species arising from the elimination of H‐5 as evidenced in the spectrum of 5‐ d ‐β‐naphthoflavone. Other previously unsuspected ions are also in evidence.