Mechanism of pH-dependent decomposition of monoalkylamine diazeniumdiolates to form HNO and NO, deduced from the model compound methylamine diazeniumdiolate, density functional theory, and CBS-QB3 calculations

Inorganic Chemistry
Andrew S DuttonK N Houk

Abstract

Isopropylamine diazeniumdiolate, IPA/NO, the product of the reaction of isopropylamine and nitric oxide, NO, decomposes in a pH-dependent manner to afford nitroxyl, HNO, in the pH range of 13 to above 5, and NO below pH 7. Theoretical studies using B3LYP/6-311+G(d) density functional theory, the polarizable continuum and conductor-like polarizable continuum solvation models, and the high-accuracy CBS-QB3 method on the simplified model compound methylamine diazeniumdiolate predict a mechanism involving HNO production via decomposition of the unstable tautomer MeNN+(O-)NHO-. The production of NO at lower pH is predicted to result from fragmentation of the amide/NO adduct upon protonation of the amine nitrogen.

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Citations

Jan 17, 2008·Analytical Chemistry·Kevin P DobmeierMark H Schoenfisch
Mar 17, 2011·Inorganic Chemistry·Debra J SalmonKatrina M Miranda
Jan 18, 2011·Antioxidants & Redox Signaling·Jenna F DuMond, S Bruce King
Jun 21, 2014·Nitric Oxide : Biology and Chemistry·Andrey A Bobko, Valery V Khramtsov
Feb 11, 2015·Free Radical Biology & Medicine·Debashree BasudharKatrina M Miranda
Mar 13, 2010·Journal of Vascular Surgery·Nick D TsihlisMelina R Kibbe
Feb 7, 2015·Free Radical Biology & Medicine·Robert van LithGuillermo A Ameer
Sep 10, 2014·Journal of Inorganic Biochemistry·Nizamuddin ShaikhSergei V Lymar
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Oct 17, 2019·Antioxidants & Redox Signaling·Hai-Jian SunJin-Song Bian
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Nov 10, 2012·The Journal of Organic Chemistry·Debanjan BiswasJoseph E Saavedra
Jul 10, 2013·The Journal of Physical Chemistry. a·Yan-Ni WangJoseph Ivanic

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