Stability of superoxide ion in imidazolium cation-based room-temperature ionic liquids
Abstract
The stability of superoxide ion (O(2)(*-)) generated chemically by dissolving KO(2) in dried dimethyl sulfoxide solutions containing imidazolium cation [e.g., 1-ethyl-3-methylimidazolium (EMI(+)) and 1-n-butyl-2,3-dimethylimidazolium (BMMI(+))] based ionic liquids (ILs) was investigated with UV-visible spectroscopic, NMR, and voltammetric techniques and an ab initio molecular orbital calculation. UV-visible spectroscopic and cyclic voltammetric measurements reveal that the O(2)(*-) species reacts with BMMI(+) and EMI(+) cations of ILs to form hydrogen peroxide. The pseudo first order rate constant for the reaction of BMMI(+) and O(2)(*-) species was found to be about 2.5 x 10(-3) s(-1). With a molecular orbital calculation, the O(2)(*-) species is understood to attack the 2-position (C-2) of the imidazolium ring (i.e., BMMI(+)) to form an ion pair complex in which one oxygen atom is bounded to C-2 and the other to the hydrogen atom of -CH(3) group attached to C-2. Eventually, the ion pair complex of BMMI(+) cation and O(2)(*-) species undergoes a ring opening reaction as evidenced with (1)H NMR measurement.
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Superoxide ions are capable of undergoing several reactions, including disproportionation, one-electron transfer, deprotonation and nucleophilic substitution.
“Superoxide ions are capable of undergoing several reactions, including disproportionation, one-electron transfer, deprotonation and nucleophilic substitution [65,66,67].”
From Superoxide Anion Chemistry—Its Role at the Core of the Innate Immunity (2023) · cites this paper as [66]
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Superoxide Anion Chemistry—Its Role at the Core of the Innate Immunity
Andrés, C. M. C., Pérez de la Lastra, J. M., Andrés Juan, C., Plou, F. J., & Pérez-Lebeña, E. (2023) · International Journal of Molecular Sciences · doi:10.3390/ijms24031841 · Cited by 342 · see citing works
- Authors
- Islam, M. M., Imase, T., Okajima, T., Takahashi, M., Niikura, Y., Kawashima, N., Nakamura, Y., & Ohsaka, T.
- Affiliations
- Tokyo Institute of Technology (JP)
- Corresponding author
- Ohsaka, Takeo
- Venue
- The Journal of Physical Chemistry A
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-01-09
- Volume
- 113
- Issue
- 5
- Pages
- 912-916
- ISSN
- 1089-5639 (ISSN-L)
- 1520-5215
- OpenAlex
- W2027144283
- Cited by
- 85
- References
- 33
- Citations by year
- 2026: 4 · 2025: 2 · 2024: 1 · 2023: 4 · 2022: 3 · 2021: 3 · 2020: 6 · 2019: 5 · 2018: 4 · 2017: 3 · 2016: 9 · 2015: 7 · 2014: 9 · 2013: 6 · 2012: 8
- FWCI
- 2.29
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- The Journal of Physical Chemistry A (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Chemical Engineering › Catalysis › Ionic liquids properties and applications
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Physical Sciences › Engineering › Electrical and Electronic Engineering › Advanced Battery Materials and Technologies
- Keywords
- superoxide, room temperature ionic liquids, imidazolium cations, 1-ethyl-3-methylimidazolium, potassium superoxide, hydrogen peroxide production, reaction kinetics, ion-pair complex, ring opening
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