Abstract
1,2-dihydroxybenzenes (DHBs) are organic compounds which are widely studied as they are applied to advanced oxidation processes (AOPs). These compounds are also related to the development of oxidative stress, wood biodegradation, and neuronal disease in humans. DHBs are metal ligands with pro-oxidant and antioxidant properties. These activities are related to their chelation properties and a consequence of the deprotonation of their hydroxyl groups. In literature, there are several pKa values for the hydroxyl groups of DHBs. These values vary depending on the experimental conditions or the algorithm used for calculation. In this work, an experimentally validated computational method was implemented in aqueous solution for pKa determination of 24 DHBs. The deprotonation order of the hydroxyl groups in DHB was determined observing a selective deprotonation, which depended on the ability of the substituent to donate or withdraw electron density over the ring.
Highlights
Introduction1,2-dihydroxybenzenes (DHBs) are organic compounds that exhibit antioxidant and/or prooxidant activities in several biological systems (Iwahashi et al, 1989; Moran et al, 1997; Nakamura et al, 2000; Schweigert et al, 2001; Gomes et al, 2003; Zang et al, 2003; Ohara et al, 2006; Prousek, 2007) depending on the reaction conditions (Salgado et al, 2013; Melin et al, 2015)
The method used to determine each pKa reported in this work is detailed in Table 2, and examples of the isosbestic points found for some DHBs are in Figure S2 in Supplementary Information
An experimental validated computational method was implemented in aqueous solution for pKa determination of different DHBs, which are high value compounds and have had a great attention for its use as versatile platforms for the design of different materials
Summary
1,2-dihydroxybenzenes (DHBs) are organic compounds that exhibit antioxidant and/or prooxidant activities in several biological systems (Iwahashi et al, 1989; Moran et al, 1997; Nakamura et al, 2000; Schweigert et al, 2001; Gomes et al, 2003; Zang et al, 2003; Ohara et al, 2006; Prousek, 2007) depending on the reaction conditions (Salgado et al, 2013; Melin et al, 2015). These works assign values between 9.14 (Nurchi et al, 2009) and 9.43 (Park, 1963) pH units for the first pKa, and values between 11.49 (Pizer and Babcock, 1977) and 13.8 pH units (Nurchi et al, 2009)
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