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Discovering and Evaluating the Reducing Abilities of Polar Alkanes and Related Family Members as Organic Reductants Using Thermodynamics.

熱力学的手法を用いた極性アルカンおよび関連化合物の還元能の評価

other in vitro not assessed

Abstract

Using a thermodynamic computational method, p-values for 69 polar alkanes (YH) in acetonitrile were determined, and thermodynamic network cards covering 22 elementary reaction steps were constructed. These cards revealed that certain polar alkanes function as electron reductants, hydride reductants, antioxidants, or hydrogen molecule reductants. A notable mechanistic distinction was identified between YH compounds and conventional hydrogen molecule reductants such as Hantzsch ester (HEH), benzothiazoline (BTH), and dihydrophenanthridine (PH): whereas XH compounds release hydrides before protons during hydrogenation, YH compounds release protons first, followed by hydrides. This sequential difference is attributed to contrasting acidic properties between the two compound classes. The redox behaviors of Y, YH, and YH2 as donors or acceptors of electrons, hydrogen atoms, hydrides, and hydrogen molecules were systematically analyzed and discussed within a thermodynamic framework.

Mechanism

Unlike conventional XH-type reductants that release hydrides before protons, polar alkanes (YH) release protons first and then hydrides during hydrogenation. This mechanistic reversal stems from differences in the acidic properties of YH versus XH compounds, leading to distinct thermodynamic and redox behaviors.

Bibliographic

Authors
Shen G, Qian BC, Fu Y, Zhu XQ
Journal
J Org Chem
Year
2022 (2022-07-15)
PMID
35786938
DOI
10.1021/acs.joc.2c01149

Tags

Mechanism:抗酸化酵素 酸化ストレス 活性酸素種

Delivery context

This is basic research at the cellular or molecular level. For human application, inhalation is the most promising delivery route, but inhalation carries explosion risk and concentration matters (empirical LFL of 10%; high-concentration devices are not recommended).

Safety notes

This is basic research at the cellular or molecular level. For human application, inhalation is the most promising delivery route, but inhalation carries explosion risk and concentration matters (empirical LFL of 10%; high-concentration devices are not recommended).

See also:

Cite as: H2 Papers — PMID 35786938. https://h2-papers.org/en/papers/35786938
Source: PubMed PMID 35786938