Benzylium Versus Tropylium-like Ion Formation: The Dissociation of Ionized 1-Methylnaphthalene

Joseph Costello; Paul Mayer

doi:10.18192/osurj.v5i1.7520

Benzylium Versus Tropylium-like Ion Formation: The Dissociation of Ionized 1-Methylnaphthalene

Authors

Joseph Costello University of Ottawa, Ottawa, ON, Canada
Paul Mayer University of Ottawa, Ottawa, ON, Canada

DOI:

https://doi.org/10.18192/osurj.v5i1.7520

Abstract

The formation of benzylium versus tropylium ions in the dissociation of gas-phase ions has a long and rich history. In this brief report, the possible formation of these two structurally isomeric ions in the dissociation of ionized 1-methylnaphthalene was explored. Hydrogen (H)-loss from 1-methylnaphthalene gave a distinct ion species compared to those generated by bromine (Br) atom-loss from 2-(bromomethyl)naphthalene, 1-methyl-4-bromonaphthalene, and 1-bromo-2-methylnaphthalene. The primary dissociation pathway for the tropylium ion structure [molecule (M)-H]⁺ ion from cycloheptatriene was H-atom loss. This was also the primary reaction for [M-H]⁺ from 1-methylnaphthalene, a result consistent with the ion-molecule reaction chemistry of Gotkis and Lifshitz, which suggested this population of ions was largely benzotropylium. The three brominated species must thus lose Br to make the naphthylmethyl cation structure as the common reacting configuration.

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Published

2026-06-17

Issue

Vol. 5 No. 1 (2026)

Section

Original Research

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