Information on the location of carbon-carbon double bonds in C6-C 23 linear alkenes from carbon addition reactions in a quadrupole ion trap equipped with a pulsed sample-inlet system.
Ion-molecule reactions of a number of alkene molecular ions with different neutral alkenes were studied in a quadrupole ion trap equipped with a pulsed sample-inlet system. The molecules studied include several isomeric unbranched hexenes, heptenes, octenes, and nonenes, as well as representative alkenes with ten, twelve, fourteen, and twenty-three carbon atoms. Transfer of structurally characteristic number of methylene units between the ionic and neutral reactants dominates the product distributions for all the alkenes studied, with the exception of 1-alkenes. Isomeric alkenes can be readily distinguished on the basis of their products from reactions with neutral alkenes. It is suggested that distonic intermediates are generated in these reactions, and that they fragment by alkene elimination after 1,2- and 1,5-hydride shifts. The ability to vary the reaction time, pressure of the neutral reagents, and the type of ions and neutral molecules present in the reaction chamber during each stage of the experiment sequence makes it possible to maximize the amount of structural information obtained for alkenes in these experiments. Use of CS 2 (+•) to generate the alkene molecular ion by charge exchange yields the same information without the need to carry out a mass-selection step for the ionized alkene.
Department of Chemistry, Purdue University, 47907, West Lafayette, Indiana, USA.
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J
Einhorn
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Kenttämaa
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Cooks