Nitration Mechanism of Aromatics: Lessons from Born-Oppenheimer Molecular Dynamics.

ABSTRACT: The nitration of aromatic compounds is a fundamental transformation in organic chemistry, traditionally understood through the Ingold-Hughes polar mechanism and, more recently, via single-electron transfer (SET) pathways. In this work, Born-Oppenheimer molecular dynamics (BOMD) simulations were employed to explore the mechanistic features of toluene nitration in a protic polar medium, specifically a concentrated sulfonitric mixture (HNO₃/H₂SO₄). Simulations at 423 K revealed the spontaneous formation of the nitronium ion (NO₂ ⁺) via double protonation of HNO₃ by H₂SO₄. Several BOMD trajectories were analyzed for the reaction between toluene and NO₂ ⁺ at 300 K, leading to four diffe

SUBMITTER: Henrique FJFS 

PROVIDER: S-EPMC12856663 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature