Recent advances in the chemistry of organic thiocyanates

Castanheiro, Thomas; Suffert, J.; Donnard, Morgan; Gulea, Mihaela

doi:10.1039/c5cs00532a

Cited by 291 publications

(145 citation statements)

References 44 publications

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“…Thiocyanate‐containing natural products have been isolated and studied for their biological activity and the thiocyanate moiety has been inserted into potential anticancer agents and inhibitors of the protozoan Trypanosoma cruzi . Additionally, the recent applications of organic thiocyanate in drug development has also let to recent advances to their chemistry and accessibility …”

Section: Introductionsupporting

confidence: 74%

Theoretical Investigation of Cyano‐Chalcogen Dimers and Their Importance in Molecular Recognition

2019

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In this manuscript the different noncovalent interactions established between (HYCN)2 dimers (Y=S, Se and Te) have been studied at the MP2 and CCSD(T) level of theory. Several homodimers have been taken into account, highlighting the capacity of these compounds to act both as electron donor and acceptor. The main properties studied were geometries, binding energy (Eb), and molecular electrostatic potential (MEP). Given the wide application of chalcogen bonds, and more specifically of cyano‐chalcogen moieties in molecular recognition, natural bond orbital (NBO), “atoms‐in‐molecules” (AIM), and electron density shift (EDS) analysis were also used to analyse the different noncovalent interactions upon complexation. The presence of hydrogen, chalcogen and dipole‐dipole interactions was confirmed and their implications on molecular recognition were analysed.

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Section: Introductionsupporting

confidence: 74%

Theoretical Investigation of Cyano‐Chalcogen Dimers and Their Importance in Molecular Recognition

2019

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“…In addition, higher concentrations of SCN − in the body result in abnormal proteins dialysis . SCN − can also be found in industrial effluents because of its frequent uses in many industrial processes such as hydrometallurgy, pesticides production, textile dyeing, printing, photography, as well as in the synthesis of some organic compounds .…”

Section: Introductionmentioning

confidence: 99%

Sensitive Amperometric Determination of Thiocyanates at Ionic Liquid Nanohybrid Kaolinite Modified Glassy Carbon Electrode

et al. 2018

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Electrochemical sensors have been developed by modifying a glassy carbon electrode with organo‐kaolinite hybrid materials. These materials were obtained by the grafting of four ionic liquids (1‐(2‐hydroxyethyl)‐4‐benzylpyridinium chloride, 1‐(2‐hydroxyethyl)‐4‐(tert‐butyl)pyridinium chloride, 1‐(2‐hydroxyethyl)‐4‐ethylpyridinium chloride and 1‐(2‐hydroxyethyl)‐4‐methylpyridinium chloride) on the interlayer aluminol surfaces of kaolinite. With the presence of ionic liquids in the interlayer space of kaolinite, the hybrid materials acquired anion exchange properties and were successfully applied as electrode modifier for the electroanalysis of thiocyanate (SCN−), an anion of medical and environmental concern. A pre‐concentration/detection strategy was used to overcome the interfering effect of the electrolytic solution. After the optimisation of some key experimental parameters (sodium nitrate as electrolyte, 5 min of accumulation time) calibration curves were plotted. Excellent linearity was obtained in the low concentration region (1×10−6 M to 4×10−5 M). The lowest detection limit (15 nM) was obtained with the benzylpyridinium functionalized kaolinite and the highest (60 nM) with the methylpyridinium functionalized kaolinite. Interfering anions (NO3−, Cl−, SO42− and CH3COO−) present in the pre‐concentration solution were found to interfere with SCN− but the sensors remained stable and produced reproducible signals. The most sensitive sensor was successfully applied for the amperometric determination of SCN− in human saliva samples.

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“…The thiocyanation of arenes plays an important role in organic synthesis [1] because the resulting products not only occur as ak ey functionality in certaina nticancer natural products [1b] but also serve as versatile starting materials for the preparation of variouss ulfur-containing compounds, especiallyh eterocycles. [1a] As ar esult,c onsiderable efforts have been devoted to the development of variousm ethods [1] of thiocyanation using (SCN) 2 , [2] N-thiocyanatosuccinimide, [3] and thiocyanate salts. [4] Among these thiocyanating agents,t he inexpensive and readilya vailablet hiocyanate salts are the most attractive.…”

Section: Introductionmentioning

confidence: 99%

Nitrogen Dioxide Catalyzed Oxidative Thiocyanation of Arenes with Ambient Air as the Terminal Oxidant

et al. 2016

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NO2 is an effective catalyst for the oxidative thiocyanation of arenes. This unique catalyst is inexpensive and separated easily from the final products because of its low boiling point. The mild reaction conditions allow a series of arenes and thiophenes to be thiocyanated smoothly in moderate to high yields. A preliminary mechanistic investigation suggests that the present reaction may proceed through a radical pathway.

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Recent advances in the chemistry of organic thiocyanates

Cited by 291 publications

References 44 publications

Theoretical Investigation of Cyano‐Chalcogen Dimers and Their Importance in Molecular Recognition

Theoretical Investigation of Cyano‐Chalcogen Dimers and Their Importance in Molecular Recognition

Sensitive Amperometric Determination of Thiocyanates at Ionic Liquid Nanohybrid Kaolinite Modified Glassy Carbon Electrode

Nitrogen Dioxide Catalyzed Oxidative Thiocyanation of Arenes with Ambient Air as the Terminal Oxidant

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