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Identification of Diels–Alder regioisomers by mass spectrometry coupled with theoretical calculations
Author(s) -
Cativiela C.,
García J. I.,
Garín J.,
Mayoral J. A.,
Orduna J.,
Salvatella L.
Publication year - 1993
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.1210280705
Subject(s) - structural isomer , cyclohexene , chemistry , mass spectrum , mass spectrometry , computational chemistry , spectral line , stereochemistry , organic chemistry , catalysis , chromatography , physics , astronomy
Abstract Differences in the mass spectra of Diels–Alder cyclohexene regioisomers are explained with the aid of a simple model based on the relative stability differences of the open‐chain structures resulting from the alternative cleavage of the C(1)–C(2) and the C(5)–C(6) bonds of the 1‐substituted cyclohexene ring. Theoretical SCF‐MO calculations at a semi‐empirical level proved to be useful tools for determining the relative stabilities of these open‐chain radical cation structures and hence in the interpretation of mass spectra and the correct assignment of regioisomer structures from these spectra.