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http://dx.doi.org/10.5012/bkcs.2003.24.3.350

The Mechanism of the Decomposition of a Bronchodilator, S-Nitroso-N-acetyl-D,L-penicillamine (SNAP), by a Bronchoconstrictor, Aqueous Sulfite: Detection of the N-Nitrosohydroxylamine-N-sulfonate ion  

Holder, Alvin A. (The University of Toledo, College of Arts of and Sciences, Department of Chemistry)
Marshall, Sophia C. (Department of Biological and Chemical Sciences, University of the West Indies)
Wang, Peng George (Department of Chemistry, Wayne State University)
Kwak, Chee-Hun (Department of Chemistry, Sunchon National University)
Publication Information
Bulletin of the Korean Chemical Society / v.24, no.3, 2003 , pp. 350-356 More about this Journal
Abstract
The mechanism of the decomposition of a bronchodilator, S-nitroso-N-acetyl-D,L-penicillamine (SNAP) by a bronchoconstrictor, aqueous sulfite, has been investigated in detail. The decomposition was studied using a conventional spectrophotometer at 336 nm over the ranges: 0.010 ≤ $[S^{IV}]_T$ ≤ 0.045 mol $dm^{-3}$, 3.96 ≤ pH ≤ 6.80 and 15.0 ≤ θ≤ 30.0 ℃, 0.60 ≤ I ≤ 1.00 mol $dm^{-3}$, and at ionic strength 1.00 mol $dm^{-3}$ (NaCl). The rate of reaction is dependent on the total sulfite concentration and pH in a complex manner, i.e., $k_{obs}\;=\;k_1K_2[S^{IV}]_T/ ([H^+]\;+\;K_2)$. At 25.0 ℃, the second order rate constant, $k_1$, was determined as $12.5\;{\pm}\;0.15\;mol^{-1}\;dm^3\;s^{-1}$. ${\Delta}H^{neq}\;=\;+32\;{\pm}\;3 kJ\;mol^{-1}\;and\;{\Delta}S^{\neq}\;=\;-138\;{\pm}\;13\;J\;mol^{-1}K^{-1}$. The N-nitrosohydroxylamine-N-sulfonate ion was detected as an intermediate before the formation of any of the by-products, namely, N-acetyl-D,L-penicillamine. The effect of concentration of aqueous copper(Ⅱ) ions on this reaction was also examined at pH 4.75, but there was no dependence on $[Cu^{2+}]$. In addition, the $pK_a$ of SNAP was determined as 3.51 ± 0.06 at 25.4 ℃ [I = 1.0 mol $dm^{-3}$ (NaCl)].
Keywords
S-Nitrosothiols; Bronchoconstrictor; Bronchodilator; Aqueous sulfite; S-Nitroso-N-acetyl-D,L-penicillamine;
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