Oxidation of Vanillyl Alcohol to Vanillic Acid by Acidified Permanganate: Kinetic, Stoichiometric, and Mechanistic Insights
Open accessAbstract
The oxidation kinetics of vanillyl alcohol by potassium permanganate in acidic medium were investigated spectrophotometrically at 25 °C under pseudo-first-order conditions by monitoring the decrease in KMnO4 absorbance at 526 nm.The reaction showed first-order dependence on oxidant, substrate, and hydrogen ion concentrations.Stoichiometric studies revealed a 1:2 ratio between vanillyl alcohol and KMnO4, confirming oxidation of the primary alcohol group to vanillic acid through an aldehyde intermediate.Product formation was verified using TLC, melting-point analysis, and UV-visible spectroscopy.The effects of various salts indicated that the reaction is largely independent of ionic strength, while halide-containing salts exhibited irregular behaviour due to possible competitive oxidation by permanganate.Temperature-dependent studies at 293-323 K provided activation parameters, including an activation energy of 30.62 kJ mol⁻¹ and a negative entropy of activation, suggesting formation of an ordered transition state.Based on the kinetic findings, a plausible mechanism involving a manganate ester intermediate in the rate-determining step has been proposed.
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Written from the paper’s full text.
TL;DR
Acidified permanganate oxidizes vanillyl alcohol to vanillic acid via a vanillin intermediate under pseudo-first-order kinetics, with first-order dependence on oxidant, substrate, and H⁺. The authors propose a manganate ester intermediate in the rate-determining step and report an activation energy of 30.62 kJ mol⁻¹ with negative entropy of activation.
Key findings
The reaction is first-order in KMnO₄, vanillyl alcohol, and hydrogen ion concentration, based on log–log plots with slopes near one. Stoichiometry is 1:2 vanillyl alcohol:KMnO₄, with vanillic acid formed through an aldehyde intermediate and verified by TLC, melting point, and UV-visible spectroscopy. Temperature studies at 293–323 K gave Ea = 30.62 kJ mol⁻¹ and a negative entropy of activation, interpreted as an ordered transition state. Added salts mostly had negligible effect on rate, but halide-containing salts showed irregular behavior attributed to possible competitive oxidation by permanganate.
Methods
Kinetics were monitored spectrophotometrically at 25 °C under pseudo-first-order conditions by following the decrease in KMnO₄ absorbance at 526 nm (methods section also states 530 nm). Vanillyl alcohol, H₂SO₄, KMnO₄, and added salts were varied; salt effects were tested at 0.01 and 0.02 M, and activation parameters were derived from rate constants at 25, 30, 35, and 40 °C. Product identity was checked by TLC, melting-point analysis, and UV-visible spectroscopy; kinetic runs were performed in triplicate and analyzed with Student’s t-test (p < 0.05).
Limitations
The paper does not state a dedicated limitations section. Evident from the text: the absorption maximum is reported inconsistently as 526 nm and 530 nm, and some tabulated kinetic data are irregular, including a negative k′ value in Table 4 and salt-table entries (e.g., AlCl₃, KI) not listed in the solution-preparation section. The mechanism is proposed from kinetic data and rate-law reasoning rather than direct trapping or spectroscopic identification of the manganate ester intermediate.
Model-written summary. Check it against the paper before relying on it.
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Claims the paper makes
0 of 24 cited sources checked · 0 supported · 0 flagged
- Findingown data
The entropy of activation is negative.
“and a negative entropy of activation”
Quote in the paperSubstantial claim - Findingcitation
The reaction's adherence to the Arrhenius law was confirmed by the observation that the rate constant rises with temperature.
“The reaction's adherence to the Arrhenius law was confirmed by the observation that the rate constant rises with temperature (Figure 3) [21].”
Quote in the paperSubstantial claim0 of 1 sources checked- cites [21]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Findingnone given
For KBr, the rate constant first increases at lower concentrations, then decreases at higher concentrations.
“For KBr, the rate constant first increases at lower concentrations, then decreases at higher concentrations.”
Quote in the paperNot a substantial claim - Findingcitation
There is no discernible sequence or pattern of rate constants for KI and KCl.
“On the contrary, there is no discernible sequence or pattern of rate constants for KI and KCl [16,17].”
Quote in the paperNot a substantial claim0 of 2 sources checked- cites [16]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [17]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Findingown data
The absorption maximum of KMnO4 was found at 530 nm.
“For all kinetic data, a strong peak was seen at 530 nm.”
Quote in the paperNot a substantial claim
- Findingown data
The reaction is first-order with respect to KMnO4.
“This demonstrates that the reaction is first-order with respect to KMnO4.”
- Also stated in: § 5.1. Effect of oxidant KMnO4 concentration: · plain
“When log(rate) was plotted against log KMnO4, a straight line with a slope of around one was produced.”
Quote in the paperSubstantial claim - Also stated in: § 5.1. Effect of oxidant KMnO4 concentration: · plain
- Findingown data
The reaction is first-order with respect to hydrogen ion concentration.
“The reaction showed first-order dependence on oxidant, substrate, and hydrogen ion concentrations.”
- Also stated in: § Conclusion · plain
“The reaction exhibited first-order dependence on oxidant, substrate, and hydrogen ion concentrations”
Quote in the paperSubstantial claim - Also stated in: § Conclusion · plain
- Findingown data
The stoichiometric ratio between vanillyl alcohol and KMnO4 is 1:2.
“Stoichiometric studies revealed a 1:2 ratio between vanillyl alcohol and KMnO4”
Quote in the paperSubstantial claim - Findingown data
The reaction is first-order with respect to vanillyl alcohol.
“The reaction showed first-order dependence on oxidant, substrate, and hydrogen ion concentrations.”
- Also stated in: § Conclusion · plain
“The reaction exhibited first-order dependence on oxidant, substrate, and hydrogen ion concentrations”
Quote in the paperSubstantial claim - Also stated in: § Conclusion · plain
- Findingown data
The activation energy is 30.62 kJ mol−1.
“including an activation energy of 30.62 kJ mol⁻¹”
Quote in the paperSubstantial claim - Findingown data
The reaction is largely independent of ionic strength.
“The effects of various salts indicated that the reaction is largely independent of ionic strength”
Quote in the paperNot a substantial claim - Findingreasoning
The rate constant is independent of ionic strength in the presence of K2SO4, MgCl2, and Ca(NO3)2.
“The rate constant is found to be independent of ionic strength in the presence of K2SO4, MgCl2, and Ca(NO3)2.”
Quote in the paperSubstantial claim - Interpretationcitation
Halide-containing salts exhibited irregular behaviour due to possible competitive oxidation by permanganate.
“while halide-containing salts exhibited irregular behaviour due to possible competitive oxidation by permanganate.”
- Also stated in: § 5.1. Effect of oxidant KMnO4 concentration: · hedged
“The participation of I⁻ and Cl⁻ ions in competing oxidation processes with permanganate, which generate reactive halogen species that block the primary oxidation route, might be the cause of this erratic behavior [18].”
Quote in the paperNot a substantial claim0 of 1 sources checked- cites [18]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Also stated in: § 5.1. Effect of oxidant KMnO4 concentration: · hedged
- Interpretationown data
Vanillyl alcohol is oxidized to vanillic acid through an aldehyde intermediate.
“confirming oxidation of the primary alcohol group to vanillic acid through an aldehyde intermediate.”
- Also stated in: § Conclusion · boosted
“stoichiometric studies confirmed the conversion of vanillyl alcohol to vanillic acid through an aldehyde intermediate.”
Quote in the paperSubstantial claim - Also stated in: § Conclusion · boosted
- Study design and conductown data
Correlation coefficients (R2) of more than 0.99 were achieved for all runs.
“correlation coefficients (R 2 ) of more than 0.99 were achieved for all runs.”
Quote in the paperSubstantial claim - Interpretationreasoning
The rate law for the oxidation is Rate = k KK1 [VOH][H+][Mn7+] (Equation 1).
“Rate= k KK1 [VOH] [H + ] [Mn 7+ ] Equation 1 Rate Law of Oxidation”
Quote in the paperSubstantial claim- The authors state this as an assumption: Vanillyl alcohol (VOH) and permanganate ion form an intermediate complex.
- Study design and conductnone given
Product formation was verified using TLC, melting-point analysis, and UV-visible spectroscopy.
“Product formation was verified using TLC, melting-point analysis, and UV-visible spectroscopy.”
Quote in the paperSubstantial claim - Interpretationown data
The negative entropy of activation suggests formation of an ordered transition state.
“suggesting formation of an ordered transition state.”
- Also stated in: § Conclusion · plain
“The evaluated activation parameters revealed the formation of an ordered transition state”
Quote in the paperSubstantial claim - Also stated in: § Conclusion · plain
- Interpretationown data
A mechanism involving a manganate ester intermediate in the rate-determining step is proposed.
“Based on the kinetic findings, a plausible mechanism involving a manganate ester intermediate in the rate-determining step has been proposed.”
- Also stated in: § Conclusion · plain
“the overall kinetic data supported a mechanism involving a manganate ester intermediate in the ratedetermining step.”
Quote in the paperSubstantial claim- The authors state this as an assumption: Vanillyl alcohol (VOH) and permanganate ion form an intermediate complex.
- Also stated in: § Conclusion · plain
- Interpretationreasoning
The rate-determining step includes both an ion and a neutral molecule.
“This suggests that the rate-determining step includes both an ion and a neutral molecule.”
Quote in the paperSubstantial claim - Premisecitation
Organic compounds with an excess of valence electrons beyond those required for bonding are more easily oxidized than ketones.
“According to a review of the literature, organic compounds like olefins, acetylenes, alcohols, phenols, aldehydes, amines, alkyl halides, thiols, sulphides, disulphides, and sulfoxides all have an excess of valence electrons beyond those required for bonding, which makes them more easily oxidized than ketones [12,13].”
Quote in the paperNot a substantial claim0 of 2 sources checked- cites [12]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [13]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Interpretationreasoning
The first sharp decline in absorbance can be explained by formation of the condensed product (manganate ester), which has a lower molar absorptivity than permanganate ion at 526 nm.
“The first sharp decline in absorbance can be explained by the formation of the condensed product (manganate ester), which has a lower molar absorptivity than the permanganate ion at 526 nm.”
Quote in the paperNot a substantial claim- The authors state this as an assumption: Vanillyl alcohol (VOH) and permanganate ion form an intermediate complex.
- Interpretationnone given
The manganate ester intermediate breaks down in a rate-determining phase requiring a two-electron transfer.
“or (V) are produced when the manganate ester intermediate breaks down in a rate-determining phase requiring a two-electron transfer.”
Quote in the paperNot a substantial claim- The authors state this as an assumption: Vanillyl alcohol (VOH) and permanganate ion form an intermediate complex.
- Classified as probably not a substantial claim. 14
- May combine two claims. 5
Probably not a substantial claim: may not pass S3 (load-bearing).
Study design and conductnone givenAll kinetic runs were performed in triplicate.
“all kinetic runs were performed in triplicate.”
Quote in the paperNot a substantial claimProbably not a substantial claim: may not pass S3 (load-bearing). May combine two claims.
Study design and conductnone givenStatistical significance was assessed using Student's t-test; p < 0.05 was considered significant.
“Statistical significance was assessed using Student's t-test; p < 0.05 was considered significant.”
Quote in the paperNot a substantial claimClassified as probably not a substantial claim.
Study design and conductcitationVanillyl alcohol was used in significant excess over KMnO4 in all kinetic simulations conducted under pseudo-first-order conditions.
“Vanillyl alcohol was used in significant excess over KMnO4 in all kinetic simulations conducted under pseudo-first-order conditions [9].”
Quote in the paperSubstantial claim0 of 1 sources checked- cites [9]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
Classified as probably not a substantial claim. May combine two claims.
PremisecitationIn the case of primary benzylic alcohols such as vanillyl alcohol, the reaction typically proceeds through formation of vanillin as an intermediate, which can undergo further oxidation to vanillic acid under strongly oxidative conditions.
“In the case of primary benzylic alcohols such as vanillyl alcohol, the reaction typically proceeds through formation of vanillin as an intermediate, which can undergo further oxidation to vanillic acid under strongly oxidative conditions.”
Quote in the paperSubstantial claim0 of 2 sources checked- cites [6]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [7]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
Probably not a substantial claim: may not pass S3 (load-bearing).
PremisecitationThe oxidation of alcohols by permanganate is generally believed to proceed through formation of a transient manganese-alkoxide or ester-like intermediate, followed by electron transfer and cleavage of the C-H bond to yield oxidized products.
“The oxidation of alcohols by permanganate is generally believed to proceed through formation of a transient manganesealkoxide or ester-like intermediate, followed by electron transfer and cleavage of the C-H bond to yield oxidized”
Quote in the paperNot a substantial claim0 of 1 sources checked- cites [4]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
Probably not a substantial claim: may not pass S3 (load-bearing).
PremisecitationDifferent Mn intermediate ions are produced.
“Different Mn intermediate ions are produced [10].”
Quote in the paperNot a substantial claim0 of 1 sources checked- cites [10]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
Probably not a substantial claim: may not pass S2 (checkable), S3 (load-bearing).
PremisecitationSelective oxidation of lignin-derived alcohols is an important route for biomass valorization and renewable aromatic chemistry.
“The selective oxidation of lignin-derived alcohols has therefore become an important route for biomass valorization and renewable aromatic chemistry [1,4,5].”
Quote in the paperNot a substantial claim0 of 3 sources checked- cites [1]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [4]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [5]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
Probably not a substantial claim: may not pass S3 (load-bearing). May combine two claims.
PremisecitationVanillyl alcohol is an important intermediate obtained from lignin depolymerization and serves as a platform molecule for producing vanillin and vanillic acid.
“Among these compounds, vanillyl alcohol is an important intermediate obtained from lignin depolymerization and serves as a platform molecule for producing vanillin and vanillic acid, which are widely used in food, fragrance, and pharmaceutical industries [1][2][3].”
Quote in the paperNot a substantial claim0 of 3 sources checked- cites [1]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [2]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [3]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
Probably not a substantial claim: may not pass S3 (load-bearing). May combine two claims.
PremisecitationSeveral studies have demonstrated that lignin-based aromatic alcohols can be efficiently upgraded through catalytic oxidation strategies, although controlling selectivity remains a key challenge.
“Several studies have demonstrated that lignin-based aromatic alcohols can be efficiently upgraded through catalytic oxidation strategies, although controlling selectivity remains a key challenge [1,4,6].”
Quote in the paperNot a substantial claim0 of 3 sources checked- cites [1]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [4]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [6]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
Probably not a substantial claim: may not pass S3 (load-bearing), S4 (based).
Interpretationnone givenManganese intermediates are converted to Mn2+ in the acidic medium by quick follow-up procedures.
“Eventually, the manganese intermediates are converted to Mn 2+ in the acidic medium by quick follow-up procedures”
Quote in the paperNot a substantial claim- The authors state this as an assumption: Vanillyl alcohol (VOH) and permanganate ion form an intermediate complex.
Probably not a substantial claim: may not pass S3 (load-bearing).
PremisecitationAlcoholic solvents such as methanol and ethanol are known to modify reaction rates in oxidation systems by altering dielectric environment and substrate-oxidant interactions.
“Alcoholic solvents such as methanol and ethanol are known to modify reaction rates in oxidation systems by altering dielectric environment and substrateoxidant interactions [8].”
Quote in the paperNot a substantial claim0 of 1 sources checked- cites [8]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
Probably not a substantial claim: may not pass S3 (load-bearing).
PremisecitationDepending on reaction conditions, Mn(VII) can undergo stepwise reduction to Mn(VI), Mn(IV), and Mn(II), enabling a variety of oxidation pathways.
“Depending on reaction conditions, Mn(VII) can undergo stepwise reduction to Mn(VI), Mn(IV), and Mn(II), enabling a variety of oxidation pathways [4,5].”
Quote in the paperNot a substantial claim0 of 2 sources checked- cites [4]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [5]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
Probably not a substantial claim: may not pass S4 (based). May combine two claims.
Interpretationnone givenVanillyl alcohol's hydroxyl group may be protonated in acidic medium, increasing the molecule's vulnerability to oxidant attack.
“Vanillyl alcohol's hydroxyl group may be protonated in an acidic medium, increasing the molecule's vulnerability to oxidant assault.”
Quote in the paperNot a substantial claim- The authors state this as an assumption: Vanillyl alcohol (VOH) and permanganate ion form an intermediate complex.
Probably not a substantial claim: may not pass S3 (load-bearing).
PremisecitationThe full or partial electropositive site on the oxidizing agent favors attack at an electronegative site of the reductant.
“The full or partial electropositive site on the oxidizing agent favors such an assault since it is expected that the reductant is being attacked at an electronegative site [15].”
Quote in the paperNot a substantial claim0 of 1 sources checked- cites [15]
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
The paper relies on this without support.
Systematic kinetic and mechanistic investigations focusing specifically on vanillyl alcohol remain limited.
“Despite extensive studies on permanganate oxidation of alcohols, systematic kinetic and mechanistic investigations focusing specifically on vanillyl alcohol remain limited.”
The paper relies on this without support.
Detailed information on reaction order, thermodynamic parameters, and solvent-dependent mechanistic variations under acidified conditions is still insufficiently explored.
“In particular, detailed information on reaction order, thermodynamic parameters, and solventdependent mechanistic variations under acidified conditions is still insufficiently explored.”
The authors state this as an assumption.
The chemical reactivities of MnO4- and MnO2- differ because their high-valency structures differ.
“The anions MnO4 -and MnO2 -differ in their high-valency structures; it makes sense to assume that their chemical reactivities would likewise differ [11].”
The paper relies on this without support.
Permanganate ion produced when O3 + MnO3 + forms is a far more potent oxidizing agent than KMnO4.
“Permanganate ion, which is produced when O3 + MnO3 + forms, is a far more potent oxidizing agent than KMnO4.”
The authors state this as an assumption.
Vanillyl alcohol (VOH) and permanganate ion form an intermediate complex.
“Assuming that vanillyl alcohol (represented as VOH) and permanganate ion form an intermediate complex, the rate law and rate equations may be written as follows”
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
Each contradiction between two passages listed here was confirmed by an independent check.
Temperature sets differ between methods and results
MajorThe methods say rate constants were obtained at 25, 30, 35, and 40°C, but the reported study range of 293-323 K corresponds to 20-50°C.
“Using rate constants found at various temperatures (25, 30, 35, and 40°C), activation parameters were computed using the Arrhenius and Eyring equations.”
“Temperature-dependent studies at 293-323 K provided activation parameters”
Listed acid-concentration runs oppose the claimed first-order acid dependence
MajorIn Table 4, runs IV-VI hold the listed alcohol and oxidant volumes constant while increasing the sulfuric acid volume from 2.5 to 15 mL. The reported rate constant falls from 1.029 to −0.049 rather than increasing with acid concentration.
“The reaction showed first-order dependence on oxidant, substrate, and hydrogen ion concentrations.”
“| IV | 4 | 2.5 | 28 | 1 | 1.029 | | V | 4 | 10 | 20 | 1 | 0.284 | | VI | 4 | 15 | 15 | 1 | -0.049 |”
Kinetic run time is mislabeled as 20 minutes
MinorA total time of 12,000 seconds is 200 minutes, not 20 minutes.
Reported 20 · recomputed 200
“Total time 12000 sec (20 min)”
KMnO4 absorption maximum is reported as both 530 and 526 nm
MinorThe wavelength scan identifies the strong peak as 530 nm, whereas the results call 526 nm the absorption maximum.
“For all kinetic data, a strong peak was seen at 530 nm.”
“A UV-Visible double-beam spectrophotometer was used to monitor the reaction by measuring the decrease in absorbance of {KMnO4} at its λmax of 526 nm.”
Specified substrate experiment cannot use substrate in excess
MinorThe substrate-concentration experiment specifies 2.0 × 10−3 to 8.0 × 10−3 M alcohol and 1.0 × 10−1 M oxidant. Throughout that range, alcohol is less concentrated than oxidant, contrary to the stated condition for all kinetic runs.
“Vanillyl alcohol was used in significant excess over KMnO4 in all kinetic simulations conducted under pseudo-first-order conditions [9].”
“Impact of Vanillyl Alcohol Concentration: varied between 2.0 × 10⁻³ and 8.0 × 10⁻³ M, with [KMnO4] = 1.0 × 10⁻¹ M and [H2SO4] = 0.1 M remaining constant.”
Salt concentration range exceeds the stated experimental levels
MinorThe methods specify salt tests at 0.01 and 0.02 M, while Table 5 also reports results at concentrations from 0.03 through 0.09 mol/dm3.
“Impact of added salts: Examined using KCl, KBr, K2SO4, MgCl2, Ca(NO3)2, and Al(NO₃)₃ at concentrations of 0.01 and 0.02 M.”
“| 0.09 | 0.0464 | 0.0377 | 0.0473 | 0.0532 | 0.0478 | 0.0491 | 0.0476 | 0.0536 |”
Specified oxidant concentration exceeds the prepared stock
MinorThe substrate-concentration experiment specifies 0.1 M KMnO4, ten times the concentration of the stated 0.01 M KMnO4 stock. Adding that stock to the reaction mixture cannot produce the specified concentration.
“Potassium permanganate stock solution (1.0 × 10⁻² M) was prepared weekly and stored in amber bottles.”
“[KMnO4] = 1.0 × 10⁻¹ M and [H2SO4] = 0.1 M remaining constant.”
Cites
The publisher hasn’t deposited this paper’s reference list.
Research works printed but not linked: 2
- R. Shimpi, R. Fadat, D.M. Janrao, M. Farooqui, A kinetic and mechanistic study on the oxidation of sulfanilamide by hexacyanoferrate (III) in aqueous alkaline medium, Journal of Chemical and Pharmaceutical Research, 6 (2014): 1011-1019.
- B. Dobhal, R. Shimpi, M. Farooqui, S. Gour, M. Ubale, Kinetics of permagnetic oxidation of 4- hydroxy acetophenone in acidic media, 7 (2015): 304-308.
- Venue
- International Journal of Drug Delivery Technology
- Publisher
- Dr. Yashwant Research Labs Pvt. Ltd.
- Published
- 2026-10-14
- Volume
- 16
- Issue
- 67s
- ISSN
- 0975-4415 (ISSN-L)
- OpenAlex
- W7221818551
- Semantic Scholar
- ffa24a30eb375a7fc9a6319324690da6de5a173a
- Cited by
- 0
- References
- 0
- FWCI
- 0.00
- Type
- journal article
- Open access
- bronze
- doi.org
- Locations
- International Journal of Drug Delivery Technology (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Oxidative Organic Chemistry Reactions
- Physical Sciences › Chemistry › Inorganic Chemistry › Vanadium and Halogenation Chemistry
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Reactions
- Keywords
- vanillyl alcohol, vanillic acid, potassium permanganate, oxidation kinetics, reaction stoichiometry, reaction mechanism, activation parameters, ionic strength effects, halide salts, pseudo-first-order kinetics
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