Abstract
The novelty of this work lies in the experimental confirmation that alkylamines react with Nitric oxide (NO) in aqueous solution at room temperature and atmospheric pressure conditions releasing HNO. We combined spectroscopic, electrochemical, and kinetic techniques to describe the reactions intermediates and characterized end products determined by UV–vis, NMR, and GC-MS. Nitrosamine and propene were detected for the reactions of diethylamine and isopropylamine, showing differential mechanisms between primary and secondary alkylamines. Finally, mechanistic analysis using ab-initio methods was performed and compared with the molecular mechanism proposed for the decomposition of NONOates. The results are discussed in the context of the growing interest in the NO/HNO interconversion reactions, required to understand their overlapping and different reactivity.
Article note:
A collection of peer-reviewed articles by past winners of the IUPAC and IUPAC-SOLVAY International Award for Young Chemists to celebrate the 60th anniversary of Pure and Applied Chemistry.
Funding source: Universidad de Buenos Aires
Award Identifier / Grant number: 20020170100595BA
Funding source: Fondo para la Investigación Científica y Tecnológica
Award Identifier / Grant number: PICT-2017-1930
Funding source: Agencia Nacional de Promoción Científica y Tecnológica
Funding source: Consejo Nacional de Investigaciones Científicas y Técnicas
About the author
Research funding
This work was financially supported by Argentinean Agency for the Promotion of Research, Technological Development, and Innovation (ANPCyT, PICT-2017-1930) and University of Buenos Aires (20020170100595BA). L.A. thanks CONICET for the fellowship grant. M.H., S.A.S., M.M. and F.D. are members of CONICET.
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Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/pac-2020-0601).
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