Quantum chemical study reveals dominant β-scission pathways for twelve C3H8N radicals, highlighting mechanisms of nitrogen migration during biomass amine pyrolysis.
C3 amines (C3H9N) are the simplest aliphatic amine subgroup encompassing primary, secondary, and tertiary isomers, playing a key role in understanding nitrogen migration during biomass thermal conversion. Despite extensive computational studies on the H abstraction rates of C3 amines, a systematic investigation of C3H8N radical reactions remains missing. The lack of data undermines the theoretical foundation for developing C3 amines kinetic sub-model. In this work, a comprehensive high-level quantum chemical study is performed on 12 C3H8N radicals derived from n-propylamine (NPA), iso-propylamine (IPA), N-methyl ethylamine (MEA), and trimethylamine (TMA), systematically exploring β-scission, intramolecular H-shift, and cyclization reaction channels. Geometry optimizations and frequency calculations are carried out at the revDSD-PBEP86-D3BJ/cc-pVTZ level. Single-point energies are refined at the CCSD(T)-F12b level with complete basis set extrapolation, core-valence correlation, and relativistic corrections. Pressure- and temperature-dependent rate constants are obtained via RRKM/master equation simulations using the MESS code. Results show that β-scission of C-C and C-N bonds dominate the consumption of C3H8N radicals. The 1,4 H shift is also another important channel for the straight-chain radicals with a primary radical center. Based on reactant structure, 12 key β-scission reactions are classified into 3 groups and analyzed individually: NP (straight-chain, primary C/N radical center), NS (straight-chain, secondary C/N radical center), and BP (branched-chain, primary C/N radical center). For NP radicals, the rate constants of primary-amine-derived radicals are closer to each other than those from secondary amines. An opposite trend is observed for NS radicals. For BP radicals, a central tertiary nitrogen atom leads to lower rate constants than a central tertiary carbon. It is found that the rate constants of the reaction that produce an alkene and a nitrogen centered radical are the fastest among the reactions in every group. The calculated rate constants are used to update a comprehensive C3 amine kinetic model, significantly improving predictions of key intermediates and products in NPA, IPA, and MEA pyrolysis. This work provides a systematic and reliable kinetic database for a C3H8N radical sub-model and lays a foundation for understanding nitrogen-migration mechanisms in biomass thermal conversion.
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Zheng et al. (2026) studied this question.
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