Recognition of nitrate by the ammonium derivative of a 20-membered dioxadiaza-calix[4]arene analog—solution and solid-state study of the anion binding properties

Moreno-Corral, Ramón; Höpfl, Herbert; Yatsimirsky, Anatoly K.; Gálvez-Ruíz, Juan Carlos; Lara, Karen Ochoa

doi:10.1016/j.tet.2015.01.005

Cited by 3 publications

(1 citation statement)

References 110 publications

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“…Because of its high water solubility and dispersion properties, it affects a wide span of area. Nitrates are mainly used as fertilizer in agriculture because of their high solubility and biodegradability [11]. For this reason, they are a major source of groundwater contamination.…”

Section: Introductionmentioning

confidence: 99%

Survey and zoning of nitrate-contaminated groundwater in Iran

Alighardashi¹,

Mehrani²

2017

JMES

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Groundwater quality management is important in arid and semi-arid regions, as in Iran. Nitrate (NO 3 -) is a common anion that contaminates groundwater. The present study determined the nitrate concentrations of aquifers in Iran. Data derived from studies in which the nitrate concentration had minimal spatial error at different periods were used for analysis. This included a total number of 2353 nitrate samples taken from wells located in all area of Iran. These were extracted from 82 articles and covered all of provinces. Furthermore, in every region, the average and maximum nitrate concentration were identified and kriging interpolation technique was used to obtain the spatial distribution of groundwater quality parameters by Arc view GIS 10.2 software. The results showed that the nitrate levels in samples from some regions were above the maximum standard level. Nitrate contamination in some regions had increased over the last 10 years. Genetic algorithms were applied to determine the relationship between average nitrate concentration and population density, consumption of drinking water and agricultural water use. The results show that water use in agricultural areas and the subsequent consumption of fertilizer are the main source of groundwater contamination with nitrate in Iran.

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Section: Introductionmentioning

confidence: 99%

Survey and zoning of nitrate-contaminated groundwater in Iran

Alighardashi¹,

Mehrani²

2017

JMES

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23‐ and 27‐Membered Macrocyclic Diorganotin(IV) Bis‐dithiocarbamates: Synthesis, Spectroscopic Characterization, DFT Calculations, and Physicochemical Analysis as Anion Receptors

et al. 2016

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Four secondary diamines with aromatic spacer groups derived from α,α′-dibromo-p-xylene and 4,4′-bis(chloromethyl)-1,1′-biphenyl have been transformed into bis-dithiocarbamate ligands and each combined with dimethyl-, di-nbutyl-, and diphenyltin(IV) dichloride to yield a total of 12 mononuclear diorganotin(IV) bis-dithiocarbamate complexes with six-coordinate metal coordination geometries and either 23-or 27-membered macrocyclic structures. The products were fully characterized by IR and NMR ( 1 H, 13 C, 119 Sn) spectroscopy and high-resolution ESI + -TOF mass spectrometry. A representative selection of the macrocyclic complexes was further examined by DFT computational studies and the relative binding [a] 3429 Scheme 1. Synthesis of the macrocyclic diorganotin(IV) bis-dithiocarbamates 1-12. The numbering scheme for the assignment of the NMR spectroscopic data is included. 3431Scheme 3. Illustration of the stereochemical differences found in the molecular structures of the four trans conformers that were geometry-optimized by DFT quantum chemical calculations by using the B3LYP/def2-TZVP method for the dimethyltin complex 1. 3432In all the structures, the Sn-S cov bonds point towards the interior of the macrocycle cavity. The organic groups attached to Eur.Titration Experiments: For the titration experiments, the receptor was employed at fixed concentrations of 1 × 10 -5 M for 3, 4, 6, and 9 and 2 × 10 -5 M for 12 using chloroform as the solvent. 0.1 M (0.2 M for 12) stock solutions of the anions were prepared in the same solvent from the corresponding tetramethyl ammonium salts. Spectral changes were observed at λ = 300-302 nm and the spectrometric titration curves were analyzed and fitted on the basis of a 1:1 host-guest complexation model using Equation (1) and the Microcal Origin 8.0 program. [23] DFT Calculations: DFT quantum chemical calculations were performed with the quantum mechanical program Gaussian 09 (version B.01) [27] using the B3LYP hybrid functional [28] in combination with the def2-TZVP basis set. [29] Geometry optimizations were realized for different starting geometries of the molecular structures, which were established by molecular modelling considering variations in the metal coordination environment (cis and trans coordina-

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p-tert-Butylthiacalix[4]arenes functionalized by N-(4’-nitrophenyl)acetamide and N,N-diethylacetamide fragments: synthesis and binding of anionic guests

Vavilova

Stoikov

2017

Beilstein J. Org. Chem.

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New p-tert-butylthiacalix[4]arenes, which are mono-, 1,2-di- and tetrasubstituted at the lower rim containing N-(4’-nitrophenyl)acetamide and N,N-diethylacetamide groups in cone and partial cone conformations have been synthesized. Their complexation ability towards a number of tetrabutylammonium salts n-Bu4NX (X = F−, Cl−, Br−, I−, CH3CO2 −, H2PO4 −, NO3 −) was studied by UV spectroscopy. The effective receptor for the anions studied as well as selective receptors for F−, CH3CO2 − and H2PO4 − ions, which based on the synthesized thiacalix[4]arenes, have been obtained. It was shown that p-tert-butylthiacalix[4]arene tetrasubstituted at the lower rim by N-(4’-nitrophenyl)acetamide moieties bonded to the anions studied with association constants within the range of 3.55 × 103–7.94 × 105 M−1. Besides, the binding selectivity for F−, Cl−, CH3CO2 −, and H2PO4 − anions against other anions was in the range of 4.1–223.9. Substituting one or two fragments in the macrocycle with N,N-diethylacetamide groups significantly reduces the complexation ability of the receptor. In contrast to the 1,3-disubstituted macrocycle containing two N-(4’-nitrophenyl)acetamide moieties, the 1,2-disubstituted thiacalix[4]arene, which contains only one such fragment and a N,N-diethylacetamide moiety, selectively binds F− anions.

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Recognition of nitrate by the ammonium derivative of a 20-membered dioxadiaza-calix[4]arene analog—solution and solid-state study of the anion binding properties

Cited by 3 publications

References 110 publications

Survey and zoning of nitrate-contaminated groundwater in Iran

Survey and zoning of nitrate-contaminated groundwater in Iran

23‐ and 27‐Membered Macrocyclic Diorganotin(IV) Bis‐dithiocarbamates: Synthesis, Spectroscopic Characterization, DFT Calculations, and Physicochemical Analysis as Anion Receptors

p-tert-Butylthiacalix[4]arenes functionalized by N-(4’-nitrophenyl)acetamide and N,N-diethylacetamide fragments: synthesis and binding of anionic guests

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