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Stereochemistry and mechanism of electron impact induced elimination reactions in acenaphthenol and acetoxyacenaphthene
Author(s) -
Manhart Daryl D.,
Brown Peter,
Hunter Duncan H.
Publication year - 1977
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.1210120507
Subject(s) - stereospecificity , mechanism (biology) , deuterium , chemistry , reaction mechanism , ionization , electron ionization , computational chemistry , elimination reaction , order (exchange) , stereochemistry , medicinal chemistry , nuclear physics , organic chemistry , physics , catalysis , ion , quantum mechanics , finance , economics
The mechanisms for elimination of H 2 O from acenaphthenol and of AcOH from acetoxyacenaphthene under low energy conditions have been determined, using regiospecific and stereospecific deuterium labeling probes, and by measurement of ionization and appearance potentials for alternative pathways. Both concerted and stepwise processes must be invoked in order to explain the experimental data. Proximity effects appear to be the most important factors in determining mechanistic type.