Synthesis and characterization of two new hydroxamic acids derivatives and their metal complexes. An investigation on the keto/enol, E/Z and hydroxamate/hydroximate forms

Adiguzel, Ekrem; Yılmaz, Fatih; Emirik, Mustafa; Özil, Musa

doi:10.1016/j.molstruc.2016.07.081

Cited by 32 publications

(22 citation statements)

References 35 publications

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“…Both Z (cis) and E (trans) conformations in Scheme 1 regularly co-exist in solvent. The concentration and environmental factors determine the ratio of Z type to E type conformations to some extent, and potential barriers are present among different conformations [33,34]. The hydroxamic acid group (-CO-NH-OH) is the functional group of the BHA [25][26][27].…”

Section: Introductionmentioning

confidence: 99%

New Insights into the Configurations of Lead(II)-Benzohydroxamic Acid Coordination Compounds in Aqueous Solution: A Combined Experimental and Computational Study

Han

Zhang

et al. 2018

Minerals

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Novel collector lead(II)-benzohydroxamic acid (Pb(II)–BHA) complexes in aqueous solution were characterized by using experimental approaches, including Ultraviolet-visible (UV-Vis) spectroscopy and electrospray ionization-mass spectrometry (ESI-MS), as well as first-principle density functional theory (DFT) calculations with consideration for solvation effects. The Job plot delineated that a single coordinated Pb(BHA)+ should be formed first, and that the higher coordination number complexes can be formed subsequently. Moreover, the Pb(II)–BHA species can aggregate with each other to form complicated structures, such as Pb(BHA)2 or highly complicated complexes. ESI-MS results validated the existence of Pb-(BHA)n=1,2 under different solution pH values. Further, the first-principles calculations suggested that Pb(BHA)+ should be the most stable structure, and the Pb atom in Pb(BHA)+ will act as an active site to attack nucleophiles. These findings are meaningful to further illustrate the adsorption mechanism of Pb(II)–BHA complexes, and are helpful for developing new reagents in mineral processing.

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Section: Introductionmentioning

confidence: 99%

New Insights into the Configurations of Lead(II)-Benzohydroxamic Acid Coordination Compounds in Aqueous Solution: A Combined Experimental and Computational Study

Han

Zhang

et al. 2018

Minerals

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“…This is because the compounds, which have arylidene‐hydrazide structure, exist as E/Z geometrical isomer from CN double bond and cis/trans amide conformers at the CONH single bond. According to the literature, the compounds which have CN double bond prefer E geometrical isomer in DMSO‐ d 6 and Z isomers can be preferred in less polar solvents by an intramolecular hydrogen bond. NH, NCH, and NCH 2 signals were observed as two sets of signals because of cis/trans conformers.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and glutathione reductase inhibitory properties of 5‐methyl‐2,4‐dihydro‐3H‐1,2,4‐triazol‐3‐one's aryl Schiff base derivatives

Balaydın

Özil

Şentürk

2018

Archiv der Pharmazie

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Glutathione reductase (GR) is responsible for the existence of the reduced glutathione (GSH) molecule, a crucial antioxidant against oxidative stress reagents. The antimalarial activities of some redox active compounds are attributed to their inhibition of antioxidant flavoenzyme GR, and inhibitors are therefore expected to be useful for the treatment of malaria. In this work, a fast and effective synthesis and the GR inhibitory properties of 5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one's aryl Schiff base derivatives are reported. For this aim, the triazol nucleus was obtained, which was substituted with identical groups: ester, hydrazide, and Schiff base system at the N-2 and N-4 nitrogen atoms. The majority of the reactions were carried out by utilizing both microwave and conventional methods in order to compare their yields and reaction times. Beside this, the occuring E/Z geometrical isomers from the CN double bond and the cis/trans amide conformers at the CONH single bond were studied. In the biological activity section of this work, it was found that all synthesized compounds have better inhibitory activity than N,N-bis(2-chloroethyl)-N-nitrosourea against GR; especially, two molecules, 6e and 6f, are the best among them. The evidence indicates that these Schiff base derivatives, with triazole ring, are strong GR inhibitors and novel antimalaria candidates.

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Section: Introductionmentioning

confidence: 99%

Novel Insights into the Configurations of Lead(II)-Benzohydroxamic Acid Coordination Compounds in Aqueous Solution: A Combined Experimental and Computational Study

He¹,

Han²,

Zhang³

et al. 2018

Preprint

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Novel collector lead(II)-benzohydroxamic acid (Pb(II)-BHA) complexes in aqueous solution were characterized by using experimental approaches, including Ultraviolet-visible (UV-Vis) spectroscopy and electrospray ionization–mass spectrometry (ESI-MS), as well as first-principle density functional theory (DFT) calculations with consideration for solvation effects. The Job plot delineated that a single coordinated Pb(BHA)+ should be formed first, and the higher coordination number complexes can be formed subsequently. Moreover, the Pb(II)-BHA species can aggregate with each other to form complicated structures, such as Pb(BHA)2 or highly complicated complexes. ESI-MS results validated the existence of Pb-(BHA)n=1,2 under different solution pH values. Further, the first-principles calculations suggested that Pb(BHA)+ should be the most stable structure, and the Pb atom in Pb(BHA)+ will act as an active site to attack nucleophiles. These findings are meaningful to further illustrate the adsorption mechanism of Pb(II)-BHA complexes in mineral processing.

show abstract

Synthesis and characterization of two new hydroxamic acids derivatives and their metal complexes. An investigation on the keto/enol, E/Z and hydroxamate/hydroximate forms

Cited by 32 publications

References 35 publications

New Insights into the Configurations of Lead(II)-Benzohydroxamic Acid Coordination Compounds in Aqueous Solution: A Combined Experimental and Computational Study

New Insights into the Configurations of Lead(II)-Benzohydroxamic Acid Coordination Compounds in Aqueous Solution: A Combined Experimental and Computational Study

Synthesis and glutathione reductase inhibitory properties of 5‐methyl‐2,4‐dihydro‐3H‐1,2,4‐triazol‐3‐one's aryl Schiff base derivatives

Novel Insights into the Configurations of Lead(II)-Benzohydroxamic Acid Coordination Compounds in Aqueous Solution: A Combined Experimental and Computational Study

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