Reaction of Amines with NO at room temperature and atmospheric pressure: is nitroxyl a reaction intermediate?
-
Mariana Hamer
,
Sebastián A. Suarez
Sebastián A. Suarez . Associate researcher CONICET, Argentina. He studied Chemistry (MSc and Ph.D.) at the University of Buenos Aires and completed a postdoc at the Argentine Atomic Energy Commission. He has been involved in several research projects studying reaction kinetics, organometallic synthesis, and bioinorganic chemistry of gasotransmitters like HNO, NO, and H2S. His main research interests include Bioinorganic and Structural Chemistry. He designs and produces new chemical systems with applications in catalysis, gas sensors, and optics. He has published more than 60 papers in reviewed journals (h = 14) and filed one PCT patent. He received the IUPAC-Solvay International Award for Young Chemists 2016, the best doctoral thesis in the area of chemistry awarded by the International Union of Pure and Applied Chemistry and the National Innovation Award (INNOVAR 2016) in the category New Technologies in Scientific Research.
,
Martina Muñoz
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.
References
[1] J. R. Lancaster. Futur. Sci. FSO59 (2015).Search in Google Scholar
[2] M. Hamer, M. A. Morales Vásquez, F. Doctorovich. The Chemistry and Biology of Nitroxyl (HNO), pp. 1–9. Elsevier (2017).10.1016/B978-0-12-800934-5.00001-3Search in Google Scholar
[3] M. D. Bartberger, W. Liu, E. Ford, K. M. Miranda, C. Switzer, J. M. Fukuto, P. J. Farmer, D. A. Wink, K. N. Houk. Proc. Natl. Acad. Sci.99, 10958–10963 (2002).10.1073/pnas.162095599Search in Google Scholar PubMed PubMed Central
[4] W. Flores-Santana, D. J. Salmon, S. Donzelli, C. H. Switzer, D. Basudhar, L. Ridnour, R. Cheng, S. A. Glynn, N. Paolocci, J. M. Fukuto, K. M. Miranda, D. A. Wink. Antioxid. Redox Signal.14, 1659–1674 (2011).10.1089/ars.2010.3841Search in Google Scholar PubMed PubMed Central
[5] M. Hamer, S. A. Suarez, N. I. Neuman, L. Alvarez, M. Muñoz, M. A. Marti, F. Doctorovich. Inorg. Chem.54, 9342–9350 (2015).10.1021/acs.inorgchem.5b01347Search in Google Scholar PubMed
[6] S. A. Suarez, N. I. Neuman, M. Muñoz, L. Álvarez, D. E. Bikiel, C. D. Brondino, I. Ivanović-Burmazović, J. L. Miljkovic, M. R. Filipovic, M. A. Martí, F. Doctorovich. J. Am. Chem. Soc.137, 4720–4727 (2015).10.1021/ja512343wSearch in Google Scholar PubMed
[7] M. Eberhardt, M. Dux, B. Namer, J. Miljkovic, N. Cordasic, C. Will, T. I. Kichko, J. de la Roche, M. Fischer, S. A. Suárez, D. Bikiel, K. Dorsch, A. Leffler, A. Babes, A. Lampert, J. K. Lennerz, J. Jacobi, M. A. Martí, F. Doctorovich, E. D. Högestätt, P. M. Zygmunt, I. Ivanovic-Burmazovic, K. Messlinger, P. Reeh, M. R. Filipovic. Nat. Commun.5, 4381 (2014).10.1038/ncomms5381Search in Google Scholar PubMed PubMed Central
[8] S. A. Suarez, M. Muñoz, L. Alvarez, M. F. Venâncio, W. R. Rocha, D. E. Bikiel, M. A. Marti, F. Doctorovich. J. Am. Chem. Soc.139, 14483–14487 (2017).10.1021/jacs.7b06968Search in Google Scholar PubMed
[9] R. S. Drago, B. R. Karstetter. J. Am. Chem. Soc.83, 1819–1822 (1961).10.1021/ja01469a012Search in Google Scholar
[10] R. S. Drago, F. E. Paulik. J. Am. Chem. Soc.82, 96–98 (1960).10.1021/ja01486a021Search in Google Scholar
[11] J. A. Hrabie, J. R. Klose, D. A. Wink, L. K. Keefer. J. Org. Chem.58, 1472–1476 (1993).10.1021/jo00058a030Search in Google Scholar
[12] K. M. Miranda, T. Katori, C. L. Torres de Holding, L. Thomas, L. A. Ridnour, W. J. McLendon, S. M. Cologna, A. S. Dutton, H. C. Champion, D. Mancardi, C. G. Tocchetti, J. E. Saavedra, L. K. Keefer, K. N. Houk, J. M. Fukuto, D. A. Kass, N. Paolocci, D. A. Wink. J. Med. Chem.48, 8220–8228 (2005).10.1021/jm050151iSearch in Google Scholar PubMed
[13] D. J. Salmon, C. L. T. De Holding, L. Thomas, K. V. Peterson, G. P. Goodman, J. E. Saavedra, A. Srinivasan, K. M. Davies, L. K. Keefer, K. M. Miranda, C. L. Torres de Holding. Inorg. Chem.50, 3262–3270 (2011).10.1021/ic101736eSearch in Google Scholar PubMed PubMed Central
[14] J. F. DuMond, B. King. Antioxid. Redox Signal.14, 1637–1648 (2011).10.1089/ars.2010.3838Search in Google Scholar PubMed PubMed Central
[15] N. Shaikh, M. Valiev, S. V. Lymar. J. Inorg. Biochem.14, 128–135 (2014).Search in Google Scholar
[16] S. A. Suárez, M. H. Fonticelli, A. A. Rubert, E. de La Llave, D. Scherlis, R. C. Salvarezza, M. A. Martí, F. Doctorovich. Inorg. Chem.49, 6955–66 (2010).10.1021/ic1007022Search in Google Scholar PubMed
[17] S. A. Suárez, D. E. Bikiel, D. E. Wetzler, M. A. Martí, F. Doctorovich. Anal. Chem.85, 10262–10269 (2013).10.1021/ac402134bSearch in Google Scholar PubMed
[18] J. L. Heinecke, C. Khin, J. C. M. Pereira, S. A. Suárez, A. V. Iretskii, F. Doctorovich, P. C. Ford. J. Am. Chem. Soc.135, 4007–4017 (2013).10.1021/ja312092xSearch in Google Scholar PubMed
[19] K. Sirsalmath, S. A. Suárez, D. E. Bikiel, F. Doctorovich. J. Inorg. Biochem.118, 134–139 (2013).10.1016/j.jinorgbio.2012.10.008Search in Google Scholar PubMed
[20] L. Álvarez, S. A. Suarez, D. E. Bikiel, J. S. Reboucas, I. Batinić-Haberle, M. A. Martí, F. Doctorovich. Inorg. Chem.53, 7351–7360 (2014).10.1021/ic5007082Search in Google Scholar PubMed
[21] M. A. Martí, S. E. Bari, D. A. Estrin, F. Doctorovich. J. Am. Chem. Soc.127, 4680–4684 (2005).10.1021/ja044632nSearch in Google Scholar PubMed
[22] K. P. Dobmeier, D. A. Riccio, M. H. Schoenfisch. Anal. Chem.80, 1247–1254 (2008).10.1021/ac702024tSearch in Google Scholar PubMed PubMed Central
[23] S. V. Lymar, V. Shafirovich, G. A. Poskrebyshev. Inorg. Chem.44, 5212–21 (2005).10.1021/ic0501317Search in Google Scholar PubMed
[24] P. G. Wang, M. Xian, X. Tang, X. Wu, Z. Wen, T. Cai, A. J. Janczuk. Chem. Rev.102, 1091–1134 (2002).10.1021/cr000040lSearch in Google Scholar PubMed
[25] S. E. Bari, V. T. Amorebieta, M. M. Gutiérrez, J. A. Olabe, F. Doctorovich. J. Inorg. Biochem.104, 30–36 (2010).10.1016/j.jinorgbio.2009.09.024Search in Google Scholar PubMed
[26] D. Basudhar, G. Bharadwaj, D. J. Salmon, K. M. Miranda. The Chemistry and Biology of Nitroxyl (HNO), pp. 11–36. Elsevier (2017).10.1016/B978-0-12-800934-5.00002-5Search in Google Scholar
Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/pac-2020-0601).
© 2020 IUPAC & De Gruyter. This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. For more information, please visit: http://creativecommons.org/licenses/by-nc-nd/4.0/
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Articles in the same Issue
- Frontmatter
- In this issue
- Preface
- Pure and Applied Chemistry Diamond Jubilee Issue
- Invited papers
- Harnessing host–guest interactions to control structure at the nanoscale
- Corrole photochemistry
- Restructuring of ultra-thin branches in multi-nucleated silicon nanowires
- Multidimensional graphene nanostructures – synthesis and applications
- Electrochemical flow systems enable renewable energy industrial chain of CO2 reduction
- A retrospective on MXene-based composites for solar fuel production
- Radicals in prebiotic chemistry
- Advances in the catalyst- and reagent-controlled site-divergent intermolecular functionalization of C(sp3)–H bonds
- Reaction of Amines with NO at room temperature and atmospheric pressure: is nitroxyl a reaction intermediate?
- A Puerto Rican chemist with coffee
