Effect of nitrogen number on the metal binding selectivity of 12-membered macrocycles

Diao, Kai-Sheng; Bai, Lijuan; Wang, Haijun

doi:10.1016/j.comptc.2010.11.026

Cited by 10 publications

(9 citation statements)

References 35 publications

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“…It can be observed that the interaction energies gradually increase with the nitrogen number. This result agrees with previous studies [18,21]. The interaction energy order is N0 < N1 < N2 < N3 < N4 < N5 < N6.…”

Section: Binding Energies and Selectivitysupporting

confidence: 83%

“…The effect of nitrogen number on the metal binding selectivity of 12-membered crown ethers (12-crown-4, aza-12-crown-4, diaza-12-crown-4, triaza-12-crown-4, and tetraza-12-crown-4) with Be 2+ , Li + or Na + ions have been reported employing the B3LYP/6-31+G** level of theory [21]. In another work, the structures and metal binding selectivity of complexes of 12-Crown-4 and its heterocyclic derivatives containing N, P, and S atoms have been reported at the same levels of theory [22].…”

Section: Article In Pressmentioning

confidence: 99%

“…Theoretical investigations have significantly helped to explain the selectity of crown ethers capturing metal ions [16][17][18][19][20]. The effect of nitrogen number on the metal binding selectivity of 12-membered crown ethers (12-crown-4, aza-12-crown-4, diaza-12-crown-4, triaza-12-crown-4, and tetraza-12-crown-4) with Be 2+ , Li + or Na + ions have been reported employing the B3LYP/6-31+G** level of theory [21].…”

Section: Article In Pressmentioning

confidence: 99%

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Theoretical study on the binding selectivity of 18-membered azacrown ethers with alkaline earth metal species

et al. 2018

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The binding selectivity of 18-membered azacrown ethers (monoaza-N1, diaza-N2, triaza-N3, tetraaza-N4, pentaaza-N5, and hexaaza-18-crown-6 N6) with Ca 2+ , Sr 2+ , Ba 2+ have been studied by density functional theory (DFT) calculations. The complex binding selectivity was analyzed in term of interaction energies, thermodynamic properties, second order interaction energies, and charge transfer effects. The geometrical study shows that Ca 2+ and azacrown complexes acquire envelope like structure, leading to shorter bond lengths. As a result, these complex systems have the highest interaction energies. Theoretical study also showed that N6 complex with alkaline earth metal ion were shown to be more stable complex than those ligand with lower nitrogen number. The interaction energy order is N0 < N1 < N2 < N3 < N4 < N5 < N6. This trend shows that the presence of more nitrogen on the crown ether cavity increases the interaction energies by approx. 7.3 % in going from N0 to N6. It is clearly showed that the contribution of the number of nitrogen play a dominant role in the binding selectivity of these systems. Keywords: DFT method, alkaline earth, aza-crown ether, metal ion, binding selectivity ABSTRAKSelektivitas kelompok aza eter mahkota (monoaza-N1, diaza-N2, triaza-N3, tetraaza-N4, pentaaza-N5, dan hexaaza-18-mahkota-6 N6) terhadap Ca 2+ , Sr 2+ , Ba 2+ telah dikaji berdasarkan teori fungsional kerapatan. Selektivitas eter mahkota diukur berdasarkan sifat energi ikatan, sifat termodinamika, energi interaksi orde kedua dan transfer muatan. Kajian parameter geometri menunjukkan bahwa kompleks Ca 2+ dan aza eter mahkota membentuk struktur seperti amplop terlipat, sehingga memiliki panjang ikatan yang lebih pendek. Akibatnya sistem kompleks ini memiliki energi interaksi yang lebih tinggi. Kajian teoritis juga menunjukkan bahwa komplek N6 dengan logam alkali tanah paling stabil. Urutan energi iteraksi adalah N0 < N1 < N2 < N3 < N4 < N5 < N6. Urutan ini menunjukkan bahwa meningkatnya jumlah atom nitrogen pada eter mahkota, meningkatkan energi interaksi 7,3 % dari N0 ke N6. Hasil kajian menunjukkan bahwa jumlah atom nitrogen memiliki peranan dominan pada selektivitas kelompok aza eter mahkota. Kata Kunci: metode DFT, alkali tanah, aza eter mahkota, ion logam, selektivitas ikatan

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Section: Binding Energies and Selectivitysupporting

confidence: 83%

Section: Article In Pressmentioning

confidence: 99%

Section: Article In Pressmentioning

confidence: 99%

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Theoretical study on the binding selectivity of 18-membered azacrown ethers with alkaline earth metal species

et al. 2018

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“…Theoretical studies have been performed on the effect of cavity size, donor atoms, electron donating and withdrawing group substitution on the metal ion-crown ether interaction [10][11][12][13][14][15]. However, very few theoretical studies have attempted to study the role of counterion, solvent types and extraction temperatures on the alkaline earth crown ether complexes.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study on the Extraction of Alkaline Earth Salts by 18-Crown-6: Roles of Counterions, Solvent Types and Extraction Temperatures

Hadisaputra¹,

Canaval²,

Pranowo³

et al. 2014

Indones. J. Chem.

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“…The structures of azacown and its complexes with alkaline ion in solvent has been reported at B3LYP/6-31 G**//RHF/6-31-G* level of theory [13]. The selectivity of crown ether with different donor atom (N, P and S) toward Li + , Na + , Be 2+ has been studied at B3LYP/6-31+G** level of theory [14][15]. In the current work, we use density functional theory (DFT) to study: (1) effect of cavity size on the structure and interaction of crown ether with Sr…”

Section: +mentioning

confidence: 99%

Extraction of Strontium(ii) by Crown Ether: Insights From Density Functional Calculation

Hadisaputra¹,

Pranowo²,

Armunanto³

2012

Indones. J. Chem.

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The structures, energetic and thermodynamic parameters of crown ethers with different cavity size, electron donating/withdrawing substituent groups and donor atoms have been determined with density functional method at B3LYP level of theory in gas and solvent phase. Small core quasi-relativistic effective core potentials was used together with the accompanying SDD basis set for Sr2+ and DZP basis set was used for crown ether atoms. Natural bond orbital (NBO) analysis was evaluated to characterize the distribution of electrons on the complexes. The interaction energy is well correlated with the values of Strontium charge after complexation, the second order interaction energies (E2) and HOMO-LUMO energy gab (∆Egab). The interaction energy and thermodynamics parameters in gas phase are reduced in solvent phase as the solvent molecules weaken the metal-crown ether interaction. The thermodynamic parameters indicated that less feasibility to extract Sr2+ ion directly from pure water without presence of organic solvent. The theoretical values of extraction energy for Sr(NO3)2 salt from aqueous solution in different organic solvent is validated by the experimental trend. This study would have strong contribution in planning the experiments to the design of specific host ligand and screening of solvent for extraction of metal ion.

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Effect of nitrogen number on the metal binding selectivity of 12-membered macrocycles

Cited by 10 publications

References 35 publications

Theoretical study on the binding selectivity of 18-membered azacrown ethers with alkaline earth metal species

Theoretical study on the binding selectivity of 18-membered azacrown ethers with alkaline earth metal species

Theoretical Study on the Extraction of Alkaline Earth Salts by 18-Crown-6: Roles of Counterions, Solvent Types and Extraction Temperatures

Extraction of Strontium(ii) by Crown Ether: Insights From Density Functional Calculation

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