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Vol. 35 No. 12 (2023): Vol 35 Issue 12, 2023

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A Spectroscopic Approach on Permanganate Oxidation of 1-[(4-Chlorophenyl)methyl]piperidin-4-amine in Presence of Ruthenium(III) Catalyst with DFT Analysis on Reaction Mechanism Pathway

https://doi.org/10.14233/ajchem.2023.30577
S. Shashidhar
Department of Chemistry, New Horizon College of Engineering (Affiliated to Visvesvaraya Technological University, Belgaum), Bengaluru-560103, India Department of Chemistry and Research in Chemistry, Visvesvaraya Technological University, SEA College of Engineering & Technology, Bangalore-560049, India
https://orcid.org/0000-0001-5745-7149
Vidyavati A. Shastry
Department of Chemistry and Research in Chemistry, Visvesvaraya Technological University, SEA College of Engineering & Technology, Bangalore-560049, India
https://orcid.org/0000-0001-7435-7932
Sampath Chinnam
Department of Chemistry, M.S. Ramaiah Institute of Technology (Affiliated to Visvesvaraya Technological University, Belgaum), Bengaluru-560054, India
https://orcid.org/0000-0002-5334-9076
Hazem Elkady
Department of Pharmaceutical Medicinal Chemistry & Drug Design, Faculty of Pharmacy (Boys), Al-Azhar University, Cairo11884, Egypt
https://orcid.org/0000-0003-0893-6703
Dalal Z. Husein
Department of Chemistry, Faculty of Science, New Valley University, El-Kharja 72511, Egypt
https://orcid.org/0000-0001-7552-0914
Anusuya Devi
Department of Chemistry, New Horizon College of Engineering (Affiliated to Visvesvaraya Technological University, Belgaum), Bengaluru-560103, India
https://orcid.org/0000-0002-3784-6822
K. Gurushantha
Department of Chemistry, M.S. Ramaiah Institute of Technology (Affiliated to Visvesvaraya Technological University, Belgaum), Bengaluru-560054, India
https://orcid.org/0000-0002-0759-9453
P.K. Asha
Department of Chemistry, New Horizon College of Engineering (Affiliated to Visvesvaraya Technological University, Belgaum), Bengaluru-560103, India
https://orcid.org/0000-0003-1071-8473

Corresponding Author(s) : P.K. Asha

ashapkind@gmail.com

Asian Journal of Chemistry, Vol. 35 No. 12 (2023): Vol 35 Issue 12, 2023

Abstract

The kinetic oxidation of 1-[(4-chlorophenyl)methyl]piperidin-4-amine (CMP) using alkaline potassium permanganate in presence of Ru(III) as catalyst was conducted spectrophotometrically at 303 K. The Pseudo first-order reaction was maintained with regard to oxidant and substrate during the reaction at an ionic strength of 0.01 mol dm-3. The first-order kinetics has been depicted with respect to catalyst Ru(III) chloride and less than unit order with substrate and medium. For the slow step, different activation parameters including ΔH# (kJ mol-1), Ea (kJ mol-1), ΔG# (kJ mol-1) and ΔS# (J K-1 mol-1) were calculated. The effect of temperature, variation of substrate concentration, oxidant, ionic strength were studied. The stoichiometry ratio of the reaction to the substrate and oxidizing agent was found to be 1:4. The products of reaction were isolated and identified as chlorobenzene and L-alanine, N-(2-aminomethylethyl)-carboxylic acid by LC-MS spectra, a suitable mechanism has been proposed and the rate laws are derived. The frontier molecular orbital (FMO) and frontier electron density (FED) of piperidiamine and the oxidative products were studied using density functional theory (DFT). The results of the theoretical calculations supported the suggested reaction pathways.

Keywords

Kinetics 1-[(4-Chlorophenyl)methyl]piperidin-4-amine Mechanism Rate law Oxidation Potassium permanganate
Shashidhar, S., Shastry, V. A., Chinnam, S., Elkady, H., Husein, D. Z., Devi, A., … Asha, P. (2023). A Spectroscopic Approach on Permanganate Oxidation of 1-[(4-Chlorophenyl)methyl]piperidin-4-amine in Presence of Ruthenium(III) Catalyst with DFT Analysis on Reaction Mechanism Pathway. Asian Journal of Chemistry, 35(12), 3005–3012. https://doi.org/10.14233/ajchem.2023.30577
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