Conversion of thiol to homodisulfide-Schiff base derivative: Synthesis, molecular structure, crystal structure and DFT studies

Ramadan, Ramadan M.; Elantabli, Fatma M.; El‐Medani, Samir M.

doi:10.1016/j.molstruc.2019.06.108

Cited by 3 publications

(3 citation statements)

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“…It was envisioned that having disulfide-containing homobifunctional Schiff base as a tridentate ligand would make a stable film on a glassy carbon electrode for the electrochemical detection of toxic metal ions from aqueous solution. Little information on ATNA with a different single-crystal structure from the present one has been reported [16]. The synthesis of ATNA was easily obtained in one step in excellent yield by refluxing the 1:1 molar ratio of 2-aminothiphenol and 2-hydroxynaphthaldehyde in absolute ethanol for 19 h (Scheme 2a).…”

Section: Synthesismentioning

confidence: 80%

“…In this regard, the Schiff base structure represents an extraordinary class of ligands because of their facile synthesis from diverse reagents, and the formation of a wide range of complexes with potential applications in different fields such as dye affinity chromatography [5], liquid crystals [6,7], nanocomposite-based polyazommethine [8], medicine [9,10], corrosion inhibitors [11], catalysis [12] and electrochemical sensors [13][14][15]. Schiff base-derived from 2-aminobenzothiophenol, on the other hand, may have an interesting geometry owing to its propensity for the in situ formed disulfide bond [16]. Accordingly, the present work was made to explore the possibility of synthesizing and using of homobifunctional tridentate disulfide Schiff base derived from 2-hydroxy-1-naphthaldehyde and 2-aminothiopheno as a selective cation sensor by an electrochemical approach.…”

Section: Introductionmentioning

confidence: 99%

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A New Cr3+ Electrochemical Sensor Based on ATNA/Nafion/Glassy Carbon Electrode

El‐Shishtawy

Rahman

Sheikh³

et al. 2020

Materials

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A new electrochemical sensor of metal cation in an aqueous solution based on homobifunctional tridentate disulfide Schiff base and named 1,1′-(-((disulfanediylbis(2,1-phenylene))bis(azaneylylidene))bis(methaneylylidene))bis(naphthalene-2-ol) (ATNA) was easily obtained quantitatively from the condensation reaction of 2-hydroxy-1-naphthaldehyde and 2-aminothiophenol, and then fully characterized by spectroscopic techniques for structure elucidation. The molecular structure of ATNA was also confirmed by a single-crystal X-ray diffraction study to reveal a new conformation in which the molecule was stabilized by the O–H…N type intramolecular hydrogen bonding interactions in both moieties. The ATNA was used as a selective electrochemical sensor for the detection of chromium ion (Cr3+). A thin film of ATNA was coated on to the flat surface of glassy carbon electrode (GCE) followed by 5 % ethanolic Nafion in order to make the modified GCE (ATNA/Nafion/GCE) as an efficient and sensitive electrochemical sensor. It was found to be very effective and selective against Cr3+ cations in the company of other intrusive heavy metal cations such as Al3+, Ce3+, Co2+, Cu2+, Ga3+, Hg2+, Mn2+, Pb2+, and Y3+. The detection limit at 3 S/N was found to be 0.013 nM for Cr3+ ions within the linear dynamic range (LDR) (0.1 nM–10.0 mM) of Cr3+ ions with r2 = 0.9579. Moreover; this work instigates a new methodology for developing the sensitive as well as selective electrochemical toxic cationic sensors in the field of environmental and health care.

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Section: Synthesismentioning

confidence: 80%

Section: Introductionmentioning

confidence: 99%

A New Cr3+ Electrochemical Sensor Based on ATNA/Nafion/Glassy Carbon Electrode

El‐Shishtawy

Rahman

Sheikh³

et al. 2020

Materials

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“…However, thiol Schiff base compounds are often susceptible to air oxidation that usually gave homodisulphide Schiff base derivatives [26]. Moreover, it was reported that solvents can induce air oxidation of thiophenols into and homo-disulphides [27]. A speculated mechanism of conversion of the thiol Schiff bases to their homo-disulphide derivatives through reaction with oxygen have been proposed [26].…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, Structural Characterization and Investigation of DNA/BSA Binding Properties of a Homo-disulphide Schiff Base Compound Carrying Oxo Propargyl Group

Köse

2022

Cumhuriyet Science Journal

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In this work, a new homo-disulphide Schiff base compound (HDSB) was prepared and its structure was characterised by common spectroscopic and analytical methods. The compound was obatined from the condensation reaction of 2-aminothiophenol and 2-hydroxy-4-(prop-2-yn-1-yloxy)benzaldehyde in benzene. In the reaction, both Schiff base condensation and oxidation of thiols into disulphide formed. The isolated compound was structurally characterized by single crystal X-ray diffraction experiment. The homo-disulphide Schiff base compound (HDSB) was screened for its DNA/BSA binding properties using UV-Vis absorption and emission spectral studies. The compound showed considerable binding affinity to double-stranded fish sperm DNA (FSds-DNA) with binding constant of 4.1 × 104 M-1. Spectral measurements suggest that HDSB interacts with DNA in a minor groove binding mode. The compound also showed binding properties towards BSA (bovine serum albumin). The incremental addition of HDSB to the BSA solution resulted in a significant decrease in the characteristic emission band of BSA in the range of 320-500 nm (λexc: 280 nm) showing the binding interactions between HDSB and BSA.

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Recent Catalytic Advances in the Synthesis of Organic Symmetric Disulfides

Ling

Khaligh

Juan

2020

COC

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Organic symmetric disulfides have been broadly studied in various fields such as synthetic intermediates for various organic transformations, agro-chemicals, biochemistry, pharmacological chemistry, industrial polymers, peptidomimetics, self-assembled monolayers (SAMs), etc. Owing to versatile applications, the search and development of efficient, environmentally friendly, mild and inexpensive methods for the preparation of organic disulfides play an important role in the organic functional group transformations. Various aspects of the S–S bond formation are available in some books on organic functional group transformations, as well as two review articles that have been published in the years 2008 and 2014 highlighting the developments of disulfide bond formation using a variety of reagents. However, investigations on new catalytic methods are being regularly reported and new types of disulfides are synthesized. The present review has attempted to systematically summarize recent catalytic advances in the process of S–S bond formation with a major focus since 2014 on highlighting mechanistic considerations, scope, advantages, and limitations. This review does not include patent literature.

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Conversion of thiol to homodisulfide-Schiff base derivative: Synthesis, molecular structure, crystal structure and DFT studies

Cited by 3 publications

References 24 publications

A New Cr3+ Electrochemical Sensor Based on ATNA/Nafion/Glassy Carbon Electrode

A New Cr3+ Electrochemical Sensor Based on ATNA/Nafion/Glassy Carbon Electrode

Synthesis, Structural Characterization and Investigation of DNA/BSA Binding Properties of a Homo-disulphide Schiff Base Compound Carrying Oxo Propargyl Group

Recent Catalytic Advances in the Synthesis of Organic Symmetric Disulfides

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