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Reactions of nitrophenide and halonitrophenide ions with acrylonitrile and alkyl acrylates in the gas phase: addition to the carbonyl group versus Michael addition
Author(s) -
Zimnicka Magdalena,
Wileńska Beata,
Sekiguchi Osamu,
Uggerud Einar,
Danikiewicz Witold
Publication year - 2012
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/jms.2042
Subject(s) - chemistry , acrylonitrile , adduct , methyl acrylate , acrylate , alkyl , ethyl acrylate , intramolecular force , medicinal chemistry , michael reaction , alcohol , molecule , halogen , addition reaction , polymer chemistry , organic chemistry , polymer , catalysis , monomer , copolymer
Gas‐phase reactions of isomeric nitrophenide ions and p ‐halonitrophenide ions with acrylonitrile, methyl acrylate, and ethyl acrylate have been studied using mass spectrometry and computational methods. Depending on the structure of the α,β‐unsaturated compound, formation of adducts to the carbonyl group of the acrylate (for methyl acrylate and ethyl acrylate) and β‐adducts (adducts of p ‐halonitrophenide ions to α,β‐unsaturated compounds in β position) was observed. Further transformations of these adducts lead to the products of elimination of an alcohol molecule and the anionic products of intramolecular substitution of a halogen atom, respectively. Copyright © 2012 John Wiley & Sons, Ltd.