Synthesis of amino acid derivative Schiff base copper(II) complexes by microwave and wet mechanochemical methods

Otani, Nao; Furuya, Tetsundo; Katsuumi, Natsuki; Haraguchi, Takeshi; Akitsu, Takashiro

doi:10.1016/j.jics.2021.100004

Cited by 15 publications

(12 citation statements)

References 17 publications

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“…Known compounds C1.1-C8.1 were prepared in the previous paper and used as described in [17]. New compounds entries C1.2-C12.2 were prepared and characterized as follows.…”

Section: Compound Synthesesmentioning

confidence: 99%

“…For the preparation of L-amino acid derivative Schiff base Cu(II) complexes, two-step reactions were employed, namely, (1) imine condensation of primary amine (L-amino acid) and aldehyde, and (2) coordination of the Cu(II) ion from an acetate source (Scheme 1). In previous work, microwave syntheses, conventional heating and mechanochemistry for the corresponding L-amino acid derivative Schiff base Cu (II) complexes (series 1) [17] were compared, and this compound library was enriched with various mono-chloride compounds (series 2) to better understand the structure-activity link between the amino acid functional group/number and place of the chlorine moiety, as well as the antibacterial activity.…”

Section: Chemistrymentioning

confidence: 99%

“…Among the solvents possessing a high tan δ, methanol is one of the most suitable solvents for microwave synthesis because of its high microwave absorption with a loss tan δ of 0.659 [16]. That is why this method was previously employed for the synthesis of copper Schiff base complexes by microwave from a 2-step procedure, lowering the global reaction time to 10 min [17], leading, for example, to di-chlorinated compounds and, thanks to the synthetic optimized method, new mono-chlorinated Schiff base copper complexes were synthesized in this work, and all these compounds were tested against model bacteria to investigate how they inhibit the growth of these bacteria.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Identification and Antibacterial Activities of Amino Acid Schiff Base Cu(II) Complexes with Chlorinated Aromatic Moieties

Otani

Fayeulle

Nakane

et al. 2022

Applied Microbiology

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Amino acid Schiff base Cu(II) complexes were synthesized under microwave irradiation using methanol as a solvent, to maximize the best conditions to obtain the attained compounds, containing aromatics possessing no, one or two chlorine atoms. The compounds’ antibacterial activities were tested against Gram-positive and Gram-negative bacteria, and the most active were tested for their antioxidant activities, and as E. coli, in particular, was found to be sensitive to these compounds, their interaction with this bacterium was investigated. It was found that, depending on the amino acid used for the formation of the Schiff base ligand, its LogPo/w mono-chlorinated or bis-chlorinated compounds are the most efficient against the tested bacteria.

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“…Known compounds C1.1-C8.1 were prepared in the previous paper and used as described in [17]. New compounds entries C1.2-C12.2 were prepared and characterized as follows.…”

Section: Compound Synthesesmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Identification and Antibacterial Activities of Amino Acid Schiff Base Cu(II) Complexes with Chlorinated Aromatic Moieties

Otani

Fayeulle

Nakane

et al. 2022

Applied Microbiology

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“…In this study, mechanochemical processing by grinding with microwave irradiation using an agitating mixer has attracted attention as a substitute for planetary ball milling. Microwave irradiation is known to be one of the factors that cause mechanochemical reactions [22,23]. Comparing microwave irradiation and mechanochemical processing via ball milling, Ribeiro et al [23] reported that mechanochemical processing by ball milling was a more effective procedure than microwave irradiation in terms of catalyst preparation and the catalytic reaction.…”

Section: Introductionmentioning

confidence: 99%

Investigation of Cerium Reduction Efficiency by Grinding with Microwave Irradiation in Mechanochemical Processing

Kato

Iwamoto²,

Tokoro

2022

Minerals

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This study evaluated the efficiency of cerium reduction by grinding with microwave irradiation in mechanochemical processing. Grinding experiments with microwave irradiation were conducted using an agitating mixer. Since the structure of the ground samples was amorphous and the cerium concentration was much lower than those of other elements, the valence change and structural change of cerium after grinding with microwave irradiation were investigated using X-ray absorption fine structure (XAFS) analysis in the cerium K-edge. The X-ray absorption near-edge structure (XANES) analysis revealed that a portion of tetravalent cerium was reduced to trivalent cerium by grinding with microwave irradiation. In addition, it was confirmed by extended X-ray absorption fine structure (EXAFS) analysis that oxygen vacancies were produced as a result of the cerium reduction reaction. To evaluate the efficiency of cerium reduction efficiency, the percentage reduction by grinding with microwave irradiation was compared to that by planetary ball milling and microwave irradiation. As a result, it was revealed that the efficiency of cerium reduction via grinding with microwave irradiation was higher than that via microwave irradiation and the same as that via planetary ball milling. Moreover, a larger amount of tetravalent cerium could be reduced to trivalent cerium by grinding with microwave irradiation than when using planetary ball milling and microwave irradiation.

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“…In order to avoid accidents due to organic solvent like them, a mechanochemical synthesis may be a good way to reduce the amount of or use of organic solvent compared to conventional synthesis in solution. So we attempted to compare conventional solution method and wet mehanochemical method to reduce methanol solvent for azocontaining amino acid derivative Schiff base copper(II) complexes [8,9].…”

Section: Introductionmentioning

confidence: 99%

Attempt to Reduce Potentially Flammable Organic Solvents in Chemical Synthesis

Akitsu

Onami

Furuya

2021

ECS

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A fire sometimes ignited an organic solvent in a chemical laboratory. A mechanochemical synthesis may be a good way to reduce the amount of organic solvents or without organic solvents compared to conventional synthesis in solutions. The solvent affected the product, namely solvent methanol acted as a ligand, although the quality of the data of X-ray crystallography is usually difficult to report in a strict research article in the case of our Azo-Schiff base metal complexes. Thus substitution of synthesis methods associated with potentially dangerous organic solvents may be possible depending on the application or purpose.

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Synthesis of amino acid derivative Schiff base copper(II) complexes by microwave and wet mechanochemical methods

Cited by 15 publications

References 17 publications

Synthesis, Identification and Antibacterial Activities of Amino Acid Schiff Base Cu(II) Complexes with Chlorinated Aromatic Moieties

Synthesis, Identification and Antibacterial Activities of Amino Acid Schiff Base Cu(II) Complexes with Chlorinated Aromatic Moieties

Investigation of Cerium Reduction Efficiency by Grinding with Microwave Irradiation in Mechanochemical Processing

Attempt to Reduce Potentially Flammable Organic Solvents in Chemical Synthesis

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