A DFT study of permanganate oxidation of toluene and its ortho-nitroderivatives
Calculations of alternative oxidation pathways of toluene and its ortho -substituted nitro derivatives by permanganate anion have been performed. The competition between methyl group and ring oxidation has been addressed. Acceptable results have been obtained using IEFPCM/B3LYP/6-31+G(d,p) calculati...
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| Published in: | Journal of molecular modeling Vol. 20; no. 2; p. 2091 |
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2014
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| Abstract | Calculations of alternative oxidation pathways of toluene and its
ortho
-substituted nitro derivatives by permanganate anion have been performed. The competition between methyl group and ring oxidation has been addressed. Acceptable results have been obtained using IEFPCM/B3LYP/6-31+G(d,p) calculations with zero-point (ZPC) and thermal corrections, as validated by comparison with the experimental data. It has been shown that ring oxidation reactions proceed via relatively early transition states that become quite unsymmetrical for reactions involving
ortho
-nitrosubstituted derivatives. Transition states for the hydrogen atom abstraction reactions, on the other hand, are late. All favored reactions are characterized by the Gibbs free energy of activation, ΔG
≠
, of about 25 kcal mol
−1
. Methyl group oxidations are exothermic by about 20 kcal mol
−1
while ring oxidations are around thermoneutrality.
Figure
Oxidation of toluene and its ortho-nitroderivatives |
|---|---|
| AbstractList | Calculations of alternative oxidation pathways of toluene and its
ortho
-substituted nitro derivatives by permanganate anion have been performed. The competition between methyl group and ring oxidation has been addressed. Acceptable results have been obtained using IEFPCM/B3LYP/6-31+G(d,p) calculations with zero-point (ZPC) and thermal corrections, as validated by comparison with the experimental data. It has been shown that ring oxidation reactions proceed via relatively early transition states that become quite unsymmetrical for reactions involving
ortho
-nitrosubstituted derivatives. Transition states for the hydrogen atom abstraction reactions, on the other hand, are late. All favored reactions are characterized by the Gibbs free energy of activation, ΔG
≠
, of about 25 kcal mol
−1
. Methyl group oxidations are exothermic by about 20 kcal mol
−1
while ring oxidations are around thermoneutrality.
Figure
Oxidation of toluene and its ortho-nitroderivatives Calculations of alternative oxidation pathways of toluene and its ortho-substituted nitro derivatives by permanganate anion have been performed. The competition between methyl group and ring oxidation has been addressed. Acceptable results have been obtained using IEFPCM/B3LYP/6-31+G(d,p) calculations with zero-point (ZPC) and thermal corrections, as validated by comparison with the experimental data. It has been shown that ring oxidation reactions proceed via relatively early transition states that become quite unsymmetrical for reactions involving ortho-nitrosubstituted derivatives. Transition states for the hydrogen atom abstraction reactions, on the other hand, are late. All favored reactions are characterized by the Gibbs free energy of activation, ΔG(≠), of about 25 kcal mol(-1). Methyl group oxidations are exothermic by about 20 kcal mol(-1) while ring oxidations are around thermoneutrality. |
| ArticleNumber | 2091 |
| Author | Adamczyk, Paweł Wijker, Reto S. Paneth, Piotr Hofstetter, Thomas B. |
| Author_xml | – sequence: 1 givenname: Paweł surname: Adamczyk fullname: Adamczyk, Paweł organization: Institute of Applied Radiation Chemistry, Faculty of Chemistry, Lodz University of Technology – sequence: 2 givenname: Reto S. surname: Wijker fullname: Wijker, Reto S. organization: Eawag, Swiss Federal Institute of Aquatic Science and Technology – sequence: 3 givenname: Thomas B. surname: Hofstetter fullname: Hofstetter, Thomas B. email: thomas.hofstetter@eawag.ch organization: Eawag, Swiss Federal Institute of Aquatic Science and Technology – sequence: 4 givenname: Piotr surname: Paneth fullname: Paneth, Piotr email: paneth@p.lodz.pl organization: Institute of Applied Radiation Chemistry, Faculty of Chemistry, Lodz University of Technology |
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| CitedBy_id | crossref_primary_10_1021_jacs_8b08371 crossref_primary_10_1016_j_gca_2020_10_027 crossref_primary_10_1021_es403597v crossref_primary_10_1016_j_cej_2018_05_018 crossref_primary_10_1021_acs_jpca_7b05474 crossref_primary_10_1039_C8EM00024G |
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| Issue | 2 |
| Keywords | B3LYP Permanganate Nitroaromatic pollutants HOMA DFT Toluene |
| Language | English |
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| Snippet | Calculations of alternative oxidation pathways of toluene and its
ortho
-substituted nitro derivatives by permanganate anion have been performed. The... Calculations of alternative oxidation pathways of toluene and its ortho-substituted nitro derivatives by permanganate anion have been performed. The... |
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| SubjectTerms | Air Pollution Characterization and Evaluation of Materials Chemistry Chemistry and Materials Science Computer Appl. in Life Sciences Computer Applications in Chemistry Hydrogen - chemistry Kinetics Manganese Compounds - chemistry Molecular Medicine Nitrogen Compounds - chemistry Nitrogen Compounds - toxicity Original Paper Oxidation-Reduction Oxides - chemistry Specific Gravity Theoretical and Computational Chemistry Thermodynamics Toluene - chemistry |
| Title | A DFT study of permanganate oxidation of toluene and its ortho-nitroderivatives |
| URI | https://link.springer.com/article/10.1007/s00894-014-2091-1 https://www.ncbi.nlm.nih.gov/pubmed/24526379 https://pubmed.ncbi.nlm.nih.gov/PMC3936135 |
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