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Accurate Standard Hydrogen Electrode Potential and Applications to the Redox Potentials of Vitamin C and NAD/NADH

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† Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan
‡ Core Research for Evolutional Science and Technology (CREST), Japan Science and Technology (JST) Agency, Kawaguchi, Saitama 332-0012 Japan
§ Department of Physics, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan
*E-mail: [email protected] (T.M.)
*E-mail: [email protected] (Y.S.)
Cite this: J. Phys. Chem. A 2015, 119, 2, 369–376
Publication Date (Web):December 16, 2014
https://doi.org/10.1021/jp508308y
Copyright © 2014 American Chemical Society
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Abstract

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We computationally evaluated the standard hydrogen electrode (SHE) potential in aqueous phase and the Gibbs energy of a proton from the experimental pKa values of alcohol molecules. From the “golden standard” CCSD(T)/aug-cc-pVTZ level calculation, we estimated the SHE potential as 4.48 V, which is very close to the IUPAC-recommended experimental value of 4.44 V. As applications to the Gaussian-3 (G3) methods, which also reproduce the “golden standard” level calculations, we computed various pKa values and redox potentials for a vitamin series. For vitamin C, we support the experimental result of +0.35 V and predict the pKa value of d-ascorbic acid to be 3.7–3.9. Using a model molecule for nicotinamide adenine dinucleotide (NAD), we reproduced the redox potential and determined the order of the proton/electron addition, based on both the proton affinity and redox potential.

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Input files for the alcohol molecules, detailed data of the Gibbs energy corrections in accurate calculations, and optimized geometries for L- and D-Asc and several structures from NAD to NADH. This material is available free of charge via the Internet at http://pubs.acs.org.

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