Formation des ions de type benzylium versus ions de type tropylium : la dissociation du 1-méthylnaphtalène ionisé
DOI :
https://doi.org/10.18192/osurj.v5i1.7520Résumé
La formation des ions benzylium par rapport aux ions tropylium lors de la dissociation d’ions en phase gazeuse possède une longue et riche histoire. Dans ce court rapport, la formation possible de ces deux ions isomères de structure lors de la dissociation du 1-méthylnaphtalène ionisé a été étudiée.
La perte d’un atome d’hydrogène (H) à partir du 1-méthylnaphtalène a produit une espèce ionique distincte de celles générées par la perte d’un atome de brome (Br) à partir du 2-(bromométhyl)naphtalène, du 1-méthyl-4-bromonaphtalène et du 1-bromo-2-méthylnaphtalène.
La principale voie de dissociation menant à la structure de l’ion tropylium, c’est-à-dire l’ion [molécule (M) − H]⁺ issu du cycloheptatriène, correspond à la perte d’un atome d’hydrogène. Cette réaction est également la voie principale pour l’ion [M − H]⁺ issu du 1-méthylnaphtalène, un résultat cohérent avec la chimie des réactions ion–molécule décrite par Gotkis et Lifshitz, ce qui suggère que cette population d’ions est majoritairement de type benzotropylium.
Ainsi, les trois composés bromés doivent perdre un atome de brome pour former la structure de cation naphtylméthyle, qui constitue la configuration réactive commune.
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