Selective complexation of alkaline earth metal ions with nanotubular cyclopeptides: DFT theoretical study

Shahangi, Fereshte; Chermahini, Alireza Najafi; Farrokhpour, Hossein; Teimouri, Abbas

doi:10.1039/c4ra08302d

Cited by 24 publications

(12 citation statements)

References 78 publications

(82 reference statements)

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“…The energies of the Zn–O coordinate bond and of other intra- and intermolecular hydrogen bonds were calculated by Espinosa’s equation where E is the bond energy (au), and V ( r c ) is the potential energy density (au) at the corresponding critical point . Espinosa’s relationship is widely employed for the energy estimation of different types of hydrogen, , van der Waals, coordinate, , and homopolar bonds …”

Section: Methodsmentioning

confidence: 99%

Alcoholic Solvent Influence on ZnO Synthesis: A Joint Experimental and Theoretical Study

2019

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Zinc oxide nanoparticles were prepared by a solvothermal synthesis using various alcoholic reaction solvents including ethanol, 1-propanol, 1-butanol, 1-pentanol, and 1-octanol, at 170 °C. The nucleation and growth processes of the ZnO nanoparticles were investigated by X-ray diffraction (XRD) and field emission scanning electron microscopy (FE-SEM) characterization, and they were corroborated by means of quantum chemical calculations at the density functional theory level (DFT). On the basis of the results of joint microstructural and theoretical study, the nucleation and preferential growth mechanism of ZnO nanoparticles is proposed. The effect of various alcoholic solvent on the overall shape and growth rate along the preferential c-axis of ZnO nanoparticles were corroborated by means of theoretical simulations of interface-solvent interaction by using nanoclusters (ZnO) n (n = 12 and 36). The (ZnO)36–CH3(CH2) n OH (n ≤ 7) interaction has been found to be spontaneous exergonic process only in the presence of 1-butanol as reaction medium with ΔG*INT = −4.95 kcal mol–1, whereas endergonic in the presence of all remaining alcohols used (ΔG*INT > 0). The results of X-ray diffraction size-strain analysis reveal that solely the use of 1-butanol as solvent leads to rather isotropic crystallite shape (D v⊥c-ax ∼12 nm, D v∥c-ax ∼12 nm), whereas in the presence of all remaining alcohols used ZnO nanoparticles grew prevailing in the c-direction to form nanorods. The alcohols of different size and polarity acts as a solvent and reactant as well as controlling agents for crystal growth, providing different binding interactions involved in both the nucleation processes and preferential growth of ZnO nanoparticles. The calculated values of E O···H and E Zn–O of (ZnO)36–CH3(CH2)7OH (1-octanol) interaction indicate a weaker interaction of the nonpolar 1-octanol and polar a little positively charged Zn surface of ZnO crystal as well as a higher preferential growth rate along the c-axis in comparison to polar alcoholic media.

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Section: Methodsmentioning

confidence: 99%

Alcoholic Solvent Influence on ZnO Synthesis: A Joint Experimental and Theoretical Study

2019

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“…However, the mechanism for most separations is still unknown in detail, so it is of particular significance to get an insight into this topic. In continuum with our preceding study on physicochemical properties of cyclic peptides [23,24,[41][42][43], in this work we report the ability of various nanotubular cyclo alanines in potential separation of leucine enantiomers by using DFT calculations. In addition, the possibility of using UV absorption spectra of enantiomers interacting with cyclic peptide as a tool for discriminating of the enantiomers is investigated using ONIOM method which stands for ''Our own N-layered Integrated molecular Orbital and molecular Mechanics'' calculations.…”

Section: Introductionmentioning

confidence: 79%

“…There are various experimental [6][7][8] and theoretical [9][10][11][12] studies dedicated to examine different aspects of this phenomenon. The cyclic peptides are used as excellent host in host-guest chemistry because they could form inclusion complexes with guest molecules [13][14][15][16][17][18][19][20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric discrimination of leucine enantiomers by nanotubular cyclic peptides: DFT and ONIOM calculation of the absorption spectra of guested enantiomers

Shahangi

Chermahini

Farrokhpour

et al. 2016

J Incl Phenom Macrocycl Chem

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In this work, the inclusion complexes of leucine as the guest and a series of cyclic peptides with four to nine alanine as building block (host molecules) were investigated by M062X/6-31 ? G (d) level of theory. The calculations predicted the stability of the enantiomers in the cavity of cyclic peptides and the possibility of distinction between the enantiomers for the used level of theory. The results indicated that the most stable aggregate is formed between CyclAla9 and R and S-leucine enantiomers and CyclALA4 have the least interaction with R and S-leucine enantiomers. Geometrical changes of leucine due to complexation and hydrogen bonding were considered. The NBO calculations for analyzing the nature of the intermolecular hydrogen bonds were performed. In another part of this work, the UV absorption spectra of complexes of R, and S-leucine with CyclAla9 calculated using ONIOM method in the gas phase and it was showed that the UV absorption spectroscopy could be used as a chirality discriminator tool in recognition of enantiomers in the gas phase.

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“…The ability of cyclic peptide to be used as a sensor for different ions has been reported in some theoretical research. 17,18 For example, Chermahini and co-workers, by employing quantum chemistry calculations, reported that three-and fourmembered CPs constructed of alanine amino acid are selective sensors for Li + in the presence of Na + , K + , Rb + , and Cs + . 17 Also, they reported the sensing ability of cyclo(L-Pro) 3 CP and cyclo(cis-Ala) 4 for selective complex formation with Li + and Be 2+ , respectively, in the presence of other alkaline earth metal ions.…”

Section: ■ Introductionmentioning

confidence: 99%

“…17 Also, they reported the sensing ability of cyclo(L-Pro) 3 CP and cyclo(cis-Ala) 4 for selective complex formation with Li + and Be 2+ , respectively, in the presence of other alkaline earth metal ions. 18 Today, nonamino acid residues have been applied for tuning CP properties. 19 Because of the importance of HCNPs applications in selective ion extraction and investigation of the role of dispersion interactions during the complex formation, we studied the ability of two hybrid cyclic peptides (HCNPs), composed of the tren-capped cryptand (HCNP1) and 1,3,5triethylbenzene-capped cryptand (HCNP2), to form selective complexes with OAC − , HSO 23 in the gas phase and DMSO as the solvent.…”

Section: ■ Introductionmentioning

confidence: 99%

Sensing Ability of Hybrid Cyclic Nanopeptides Based on Thiourea Cryptands for Different Ions, A Joint DFT-D3/MD Study

2017

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Theoretical studies, including quantum chemistry (QM) calculations and 25 ns molecular dynamic (MD) simulations, were performed on two types of hybrid cyclic nanopeptides (HCNPs) that are constructed of tren-capped cryptand (HCNP1) and 1,3,5-triethylbenzene-capped cryptand (HCNP2) for selective complex formation with OAC, NO, HSO, F, Br, and Cl ions in the gas phase and DMSO. Obtained data by M05-2X, M05-2X-D3, B3LYP, and B3LYP-D3 functionals indicated that HCNPs form a stable complex with F in comparison to other ions. DFT-D3 results and quantum theory of atoms in molecules (QTAIM) analysis indicated that dispersion and electrostatic interactions are the most important driving forces in HCNP-ion complex formation, respectively. Moreover, HOMO-LUMO analysis reveals that the reactivity of HCNP2, due to a lower band gap, is more than HCNP1. High sensing ability of the studied HCNPs for different ions was confirmed by Fermi level shifting of HNCPs to higher values during the complex formation. Finally, MD simulation results in DMSO are in good agreement with QM calculations and indicate that F forms the most stable complexes with HCNPs because of stronger electrostatic interactions.

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Selective complexation of alkaline earth metal ions with nanotubular cyclopeptides: DFT theoretical study

Cited by 24 publications

References 78 publications

Alcoholic Solvent Influence on ZnO Synthesis: A Joint Experimental and Theoretical Study

Alcoholic Solvent Influence on ZnO Synthesis: A Joint Experimental and Theoretical Study

Enantiomeric discrimination of leucine enantiomers by nanotubular cyclic peptides: DFT and ONIOM calculation of the absorption spectra of guested enantiomers

Sensing Ability of Hybrid Cyclic Nanopeptides Based on Thiourea Cryptands for Different Ions, A Joint DFT-D3/MD Study

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