Advances in DFT

Nagy, Á.

doi:10.1002/qua.25138

Cited by 2 publications

(1 citation statement)

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“…Even though the phenoxy cation radical or phenyloxonium cation can be used as highly reactive species in various organic reactions [24], the thermodynamics of individual electron and proton transfer reactions that generate these species was systematically studied only for resorcinol, catechol and p ‐hydroquinone containing two hydroxyl groups [25]. With respect to such published results [8, 10, 26] and remaining open problems, we decided to present theoretical density functional theory (DFT) [27] calculations of monosubstituted phenols (see Figure 1 and Table 1). Twelve selected compounds involve derivatives with electron‐withdrawing, as well as electron‐donating substituents in ortho , meta or para positions.…”

Section: Introductionmentioning

confidence: 99%

On energetics of proton and electron transfer of selected phenol derivatives: Theoretical investigation of radical and oxonium cations

Kováčová

Michalík

Lukeš

2023

Int J of Quantum Chemistry

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In this paper, the systematic theoretical study of phenol and 36 compounds representing various ortho, meta and para‐substituted (R‐PhOH) phenols is presented. The hydroxyl group acidity is a characteristic feature of phenol which can be modified using substitution of phenyl ring. The proton‐coupled electron transfer was investigated for parent neutral phenols, R‐PhOH, their cation radicals, R‐PhOH+•, and oxonium cations, R‐PhOH2+. Density functional theory calculations were combined with solvent continuum model for water and dimethyl sulfoxide environment. For aqueous solution, the Pourbaix diagrams (electrochemical potential vs. pH) were constructed from the theoretically predicted acidity constants and electrochemical standard potentials. From the thermodynamic point of view, the obtained theoretical results allow the estimation of the thermodynamically preferred process and alternative reaction pathways of phenolic derivatives in very acidic media.

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