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Article

Synthesis, Structures, Electrochemistry, and Catalytic Activity towards Cyclohexanol Oxidation of Mono-, Di-, and Polynuclear Iron(III) Complexes with 3-Amino-2-Pyrazinecarboxylate

by
Anirban Karmakar
1,*,
Luísa M.D.R.S. Martins
1,*,
Yuliya Yahorava
2,
M. Fátima C. Guedes da Silva
1 and
Armando J. L. Pombeiro
1,*
1
Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049–001 Lisbon, Portugal
2
Department of Chemistry, Technology of Electrochemical Production and Electronic Engineering Materials, Belarusian State Technological University, 13a Sverdlova str., 220006 Minsk, Belarus
*
Authors to whom correspondence should be addressed.
Appl. Sci. 2020, 10(8), 2692; https://doi.org/10.3390/app10082692
Submission received: 20 March 2020 / Revised: 7 April 2020 / Accepted: 9 April 2020 / Published: 13 April 2020
(This article belongs to the Special Issue Advances on Coordination Chemistry with Nitrogen Ligands and Its Applications)
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Abstract

The synthesis and characterization of a set of iron(III) complexes, viz. the mononuclear [Fe(L)3] (1) and [NHEt3][Fe(L)2(Cl)2] (2), the dinuclear methoxido-bridged [Fe(L)2(μ-OMe)]2.DMF.1.5MeOH (3), and the heteronuclear Fe(III)/Na(I) two-dimensional coordination polymer [Fe(N3)(μ-L)2(μ-O)1/2(Na)(μ-H2O)1/2]n (4), are reported. Reactions of 3-amino-2-pyrazinecarboxylic acid (HL) with iron(III) chloride under different reaction conditions were studied, and the obtained compounds were characterized by elemental analysis, Fourier Transform Infrared (FT-IR) spectroscopy, and X-ray single-crystal diffraction. Compound 1 is a neutral mononuclear complex, whereas 2 is mono-anionic with its charge being neutralized by triethylammonium cation. Compounds 3 and 4 display a di-methoxido-bridged dinuclear complex and a two-dimensional heterometallic Fe(III)/Na(I) polynuclear coordination polymer, respectively. Compounds 3 and 4 are the first examples of methoxido- and oxido-bridged iron(III) complexes, respectively, with 3-amino-2-pyrazinecarboxylate ligands. The electrochemical study of these compounds reveals a facile single-electron reversible Fe(III)-to-Fe(II) reduction at a positive potential of 0.08V vs. saturated calomel electrode (SCE), which is in line with their ability to act as efficient oxidants and heterogeneous catalysts for the solvent-free microwave-assisted peroxidative oxidation (with tert-butyl hydroperoxide) of cyclohexanol to cyclohexanone (almost quantitative yields after 1 h). Moreover, the catalysts are easily recovered and reused for five consecutive cycles, maintaining a high activity and selectivity.
Keywords: Iron(III) complex; Crystal structure; Electrochemistry; Catalysis; Oxidation reaction Iron(III) complex; Crystal structure; Electrochemistry; Catalysis; Oxidation reaction
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MDPI and ACS Style

Karmakar, A.; M.D.R.S. Martins, L.; Yahorava, Y.; C. Guedes da Silva, M.F.; J. L. Pombeiro, A. Synthesis, Structures, Electrochemistry, and Catalytic Activity towards Cyclohexanol Oxidation of Mono-, Di-, and Polynuclear Iron(III) Complexes with 3-Amino-2-Pyrazinecarboxylate. Appl. Sci. 2020, 10, 2692. https://doi.org/10.3390/app10082692

AMA Style

Karmakar A, M.D.R.S. Martins L, Yahorava Y, C. Guedes da Silva MF, J. L. Pombeiro A. Synthesis, Structures, Electrochemistry, and Catalytic Activity towards Cyclohexanol Oxidation of Mono-, Di-, and Polynuclear Iron(III) Complexes with 3-Amino-2-Pyrazinecarboxylate. Applied Sciences. 2020; 10(8):2692. https://doi.org/10.3390/app10082692

Chicago/Turabian Style

Karmakar, Anirban, Luísa M.D.R.S. Martins, Yuliya Yahorava, M. Fátima C. Guedes da Silva, and Armando J. L. Pombeiro. 2020. "Synthesis, Structures, Electrochemistry, and Catalytic Activity towards Cyclohexanol Oxidation of Mono-, Di-, and Polynuclear Iron(III) Complexes with 3-Amino-2-Pyrazinecarboxylate" Applied Sciences 10, no. 8: 2692. https://doi.org/10.3390/app10082692

APA Style

Karmakar, A., M.D.R.S. Martins, L., Yahorava, Y., C. Guedes da Silva, M. F., & J. L. Pombeiro, A. (2020). Synthesis, Structures, Electrochemistry, and Catalytic Activity towards Cyclohexanol Oxidation of Mono-, Di-, and Polynuclear Iron(III) Complexes with 3-Amino-2-Pyrazinecarboxylate. Applied Sciences, 10(8), 2692. https://doi.org/10.3390/app10082692

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