Efficient synthesis and metal cations complexation of some novel dinaphthosulfide-substituted macrocyclic diamides

Shockravi, Abbas; Shamsipur, Mojtaba; Fattahi, Hanif; Taghdiri, Mehdi; Heidaryan, Davood; Alizadeh, Kamal; Rostami, Esmael; Abbaszadeh, Mehdi; Yousefi, Ali Akbar

doi:10.1007/s10847-008-9408-6

Cited by 22 publications

(21 citation statements)

References 35 publications

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“…[20][21][22] Related binaphthyl sulfide based macrocycles have been synthesized in our research group and used in conductance study of complexation with several different metal ions. [23][24][25] All these observations in these series of macrocycles proved that the presence of sulfide atom play an important role in Host-Guest chemistry. Also variety of macrocycles containing pyridine such as dimethyl-2,6-pyridine dicarboxylates and polyamine fragments have attracted much interest of many research groups during last decade.…”

Section: Introductionmentioning

confidence: 67%

“…[33][34][35] We have also examined such factors in DNS and pyridine based systems and studied them as host molecules in the presence of different metal cations in which the best selectivity and stability was found for Hg 2+ and Cu 2+ complexes. 24,36,37 In this work, we wish to report the effect of alkaline metal cations (Li + , Na + , K + , and Cs + )…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of new aza- and thia-crown ethers and their metal ion templates synthesis as model case study

Kamali¹,

Shockravi²,

Mohtasham³

et al. 2014

Arkivoc

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Four new thia-and four new aza-crown ethers were synthesized using the reaction of ethylene glycols ditosylated with 1,1´-(2,2´-dihydroxynaphthyl)sulfide (DNS) and 2,6-bis(3-hydroxyphenyl)-4-phenylpyridine in acetonitrile as solvent in the presence of bases (LiOH, NaOH, KOH and Cs 2 CO 3 ). In the synthesis of macrocycles based on DNS, the template effects of alkaline metal ions; Li + , Na + , K + and Cs + on the reaction yields were investigated. Sodium template generally was more effective for the synthesis of all four macrocycles. Relatively, good yields of 15-and 18-membered macrocycles were obtained in the presence of all kinds of applied cations. K + Cation was more effective template ion than Na + in the formation of 18-membered macrocycles due to their larger cavity size compared to the 15-membered cycles. The structures of macrocycles were confirmed by CHN/O analysis, IR, 1 H NMR, 13C NMR and mass spectrometry.

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Section: Introductionmentioning

confidence: 67%

Section: Introductionmentioning

confidence: 99%

Synthesis of new aza- and thia-crown ethers and their metal ion templates synthesis as model case study

Kamali¹,

Shockravi²,

Mohtasham³

et al. 2014

Arkivoc

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“…Compound 1 was synthesized based on the reported procedure involving the reaction of sulfur dichloride and 2-naphthol, the corresponding diester (2) was prepared by the reaction of dinaphthol (1) and chloromethyl acetate in refluxing acetonitrile in the presence of potassium carbonate and catalytic amounts of potassium iodide [28]. Diester (2) was reacted with ethanol amine in basic methanol solution at room temperature to produce compound (3).…”

Section: Resultsmentioning

confidence: 99%

Efficient Synthesis of a New Podand and Application as a Suitable Carrier for Silver Ion‐Selective Electrode

Mashhadizadeh¹,

Shockravi²,

Khoubi³

et al. 2009

Electroanalysis

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A new podand of 1,1'-thia-bis-[1-(chloroethan-2-acetamid-a-oxy)] naphtol was synthesized and used as a suitable carrier for Ag þ PVC membrane electrode. The electrode exhibited linear response with a Nernstian slope of (59.5 AE 0.8 mV/decade) within a wide concentration range of 1.0 Â 10 À7 to 1.5 Â 10 À2 mol L À1 silver ions. The electrode had a fast response time of < 10 s and detection limit of 8.6 Â 10 À8 mol L À1 with a working pH range from 3.7 to 9.0. The electrode was highly selective for Ag(I) ions over a large number of cations such as alkali, alkaline earth, and heavy metal ions. The proposed sensor has been applied as an indicator electrode for indirect determination of vitamin B 1 in tablets by determination of Cl À ions in this compound with a standard solution of Ag(NO 3 ).

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“…The synthesis and complexation properties of sulfurcontaining macrocyclic diamides are attracting the interest of researchers, because of their ability to coordinate transition metal ions [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

“…In this article, we have developed investigations on new dinaphthosulfide-substituted macrocyclic diamides with 15, 16 and 17-membered rings synthesized by Shockravi et al [11]. These ligands are considered as multidentate macrocycles including amidic nitrogenes.…”

Section: Introductionmentioning

confidence: 99%

Study on the interaction between dinaphthosulfide-substituted macrocyclic diamides and some metal ions: experimental measurements vs. quantum mechanical calculations

Taghdiri

Behjatmanesh–Ardakani

Shockravi³

et al. 2011

J Incl Phenom Macrocycl Chem

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Complexation properties of dinaphthosulfidesubstituted macrocyclic diamides 1 and 2 with some metal cations that have been obtained by conductometric method are described with quantum mechanics calculations. To do this, the most stable structures of ligands, Hg 2? -ligand complexes, ligand-MeOH and ClO 4 --MeOH are optimized at HF/Lanl2dz level of theory and the most important interactions are analyzed by atoms in molecules (AIM) theory. These calculations predict the existence of strong interaction between Hg 2? cation and ligands 1 and 2, particularly, S-Hg 2? interaction. The different conductometric behaviors of complexation of ligands 1 and 2 with metal ions are interpreted on the basis of the calculated intramolecular hydrogen bonds in ligands and intermolecular hydrogen bonds between ligands and methanol as a solvent and perchlorate as a counter ion. In addition, binding energies between Hg 2? and ligands are also calculated by HF/Lanl2dz level of theory. Results show that all theoretical predictions are in line agreement with the experimental data.

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Efficient synthesis and metal cations complexation of some novel dinaphthosulfide-substituted macrocyclic diamides

Cited by 22 publications

References 35 publications

Synthesis of new aza- and thia-crown ethers and their metal ion templates synthesis as model case study

Synthesis of new aza- and thia-crown ethers and their metal ion templates synthesis as model case study

Efficient Synthesis of a New Podand and Application as a Suitable Carrier for Silver Ion‐Selective Electrode

Study on the interaction between dinaphthosulfide-substituted macrocyclic diamides and some metal ions: experimental measurements vs. quantum mechanical calculations

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