Theoretical study on the structure and conformational features of distally dibromo-dipropoxythiacalix[4]arene derivatives and their Zn2+ complexes

Suwattanamala, A.; Magalhães, Alexandre L.; Gomes, J.A.N.F.

doi:10.1007/s00214-006-0173-6

Cited by 6 publications

(4 citation statements)

References 43 publications

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“…Suwattanamala et al 988 carried out B3LYP and PBE0 calculations on dipropoxythiacalix [4]arenes in chloroform solvent and examined the preferred metal coordination modes in their Zn 2+ complexes by using B3LYP.…”

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confidence: 99%

Density functional theory for transition metals and transition metal chemistry

Cramer

Truhlar

2009

Phys. Chem. Chem. Phys.

1,515

1,342

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We introduce density functional theory and review recent progress in its application to transition metal chemistry. Topics covered include local, meta, hybrid, hybrid meta, and range-separated functionals, band theory, software, validation tests, and applications to spin states, magnetic exchange coupling, spectra, structure, reactivity, and catalysis, including molecules, clusters, nanoparticles, surfaces, and solids.

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confidence: 99%

Density functional theory for transition metals and transition metal chemistry

Cramer

Truhlar

2009

Phys. Chem. Chem. Phys.

1,515

1,342

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“…Theoretical studies of calix[4]arenes, thiacalix[4]arenes, and their derivatives to date have predominantly focused on the investigation of ground-state properties, such as conformations, − binding sites, and binding energy of metal complexes. − Only a few studies have been performed examining the UV spectra and excited-state properties of these molecules using TD-DFT. − Fu et al performed TD-DFT calculations to simulate the absorption and emission spectra of neutral TCA and its complex with tetranuclear cadmium(II), in which the phenol group of thiacalix[4]arene was deprotonated . The calculated results were in excellent agreement with the experimental data.…”

Section: Introductionmentioning

confidence: 99%

TD-DFT Study on Thiacalix[4]arene, the Receptor of a Fluorescent Chemosensor for Cu²⁺

Chen

2017

J. Phys. Chem. A

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The electronic and spectral properties of p-tert-butylthiacalix[4]arene (TCA) and its Cu complexes (CuTCA and CuTCA) were characterized by time-dependent density functional theory (TD-DFT). Geometries of TCA, CuTCA, and CuTCA were optimized at the CAM-B3LYP/6-31+G(d,p) level of theory in water using the conductor-like polarizable continuum model. The absorption spectra of TCA, CuTCA, and CuTCA were demonstrated by TD-DFT method. The quenching mechanism of perylene as the fluorophore of a chemosensor based on thiacalix[4]arene was discussed. The addition of Cu to TCA introduced a series of low-lying excited states involving copper d orbitals. The overlap between absorption of TCA complexes and emission of perylene indicated that the quenching of perylene fluorescence is due to fluorescence resonance energy transfer.

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“…Also, no structure containing the sulfur atom coordination mode of binding was found for Zn 2+ complexes of dibromo-dipropoxythiacalix [4]arene and dipropoxythiacalix [4]arene, computed using hybrid DFT with a small basis set. 20 In this paper we will model relative stabilities of configurational and conformational isomers of the p-tert-butylthiacalix- [4]arene tetra(N-methyl)amide (shown on Scheme 2) and the structure of its complexes with potassium and silver ions based on the results of DFT calculations. K and Ag were selected to be objects of this study because they give two polar types of cationsshard and soft Lewis acidssand have the same charge, and because of their biological and environmental importance.…”

Section: Introductionmentioning

confidence: 99%

“…For both metal ions, the most stable structure of the thiacalix[4]arene−metal ion complex is the second deprotonated species possessing opposite pattern and the metal coordinated to two phenolate oxygens and two phenol oxygens. Also, no structure containing the sulfur atom coordination mode of binding was found for Zn 2+ complexes of dibromo-dipropoxythiacalix[4]arene and dipropoxythiacalix[4]arene, computed using hybrid DFT with a small basis set …”

Section: Introductionmentioning

confidence: 99%

Modeling K⁺ and Ag⁺ Complexation by Thiacalix[4]arene Amides Using DFT: The Role of Intramolecular Hydrogen Bonding

et al. 2009

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Complexation of methyl-glycine-amide functionalized thiacalix[4]arene with K(+) and Ag(+) has been studied using density functional theory (DFT) in the gas phase. To account for the conformational possibilities of the ligand, the free ligand and its potassium complexes were subjected to global minima searches on the molecular mechanics (MM) level of theory with the OPLS (optimized potentials for liquid simulations) force field. For the free ligand, the order of the energies and geometries of the ligand conformers is in agreement between MM and DFT; however, the position of K(+) in the ligand's cavity was predicted differently by these methods. Hydrogen bonding of amide hydrogens in the ligands' podand arms was found to take place predominantly with the ether oxygens of the same arm rather than the other arms' carbonyls. According to DFT calculations, the silver cation preferred to coordinate with one sulfur bridge and three carbonyl groups, whereas potassium cation favored interaction with the four carbonyl oxygens of the podand amide arms. Neither cation preferred the N-mode of coordination. For all obtained conformers, intramolecular hydrogen bonds disfavor complexation, increasing the preorganizational energy to be paid.

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Theoretical study on the structure and conformational features of distally dibromo-dipropoxythiacalix[4]arene derivatives and their Zn2+ complexes

Cited by 6 publications

References 43 publications

Density functional theory for transition metals and transition metal chemistry

Density functional theory for transition metals and transition metal chemistry

TD-DFT Study on Thiacalix[4]arene, the Receptor of a Fluorescent Chemosensor for Cu²⁺

Modeling K⁺ and Ag⁺ Complexation by Thiacalix[4]arene Amides Using DFT: The Role of Intramolecular Hydrogen Bonding

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Theoretical study on the structure and conformational features of distally dibromo-dipropoxythiacalix[4]arene derivatives and their Zn2+ complexes

Cited by 6 publications

References 43 publications

Density functional theory for transition metals and transition metal chemistry

Density functional theory for transition metals and transition metal chemistry

TD-DFT Study on Thiacalix[4]arene, the Receptor of a Fluorescent Chemosensor for Cu2+

Modeling K+ and Ag+ Complexation by Thiacalix[4]arene Amides Using DFT: The Role of Intramolecular Hydrogen Bonding

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TD-DFT Study on Thiacalix[4]arene, the Receptor of a Fluorescent Chemosensor for Cu²⁺

Modeling K⁺ and Ag⁺ Complexation by Thiacalix[4]arene Amides Using DFT: The Role of Intramolecular Hydrogen Bonding