Elucidating H/D-Exchange Mechanism of Active Hydrogen in Aniline and Benzene-1,2-dithiol

Arif Ahmed, Syful Islam, Sunghwan Kim

Research output: Contribution to journalArticlepeer-review

Abstract

In this study, the hydrogen/deuterium (HDX) exchange mechanism of active hydrogen, nitrogen, and sulfur-containing polycyclic aromatic hydrocarbon (PAH) dissolved in toluene and deuterated methanol by atmospheric pressure photoionization (APPI) is investigated. The comparison of the data obtained using APPI suggests that aniline and benzene-1,2-dithiol contain two exchanging hydrogens. The APPI HDX that best explains the experimental findings was investigated with the use of quantum mechanical calculations. The HDX mechanism is composed of a two-step reaction: in the first step, analyte radical ion gets deuterated, and in the second step, the hydrogen transfer occurs from deuterated analyte to de-deuterated methanol to complete the exchange reaction. The suggested mechanism provides fundamentals for the HDX technique that is important for structural identification with mass spectrometry. This paper is dedicated to Professor Seung Koo Shin for his outstanding contributions in chemistry and mass spectrometry.

Original languageEnglish
Pages (from-to)146-151
Number of pages6
JournalMass Spectrometry Letters
Volume12
Issue number4
DOIs
StatePublished - Dec 2021

Keywords

  • Atmospheric pressure photoionization (APPI)
  • Hydrogen/deuterium exchange (HDX)
  • Potential energy surface
  • Quantum mechanical calculation

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