The use of a molecular balance derived from 5,5′-bipyrazole to calculate π−π stacking interactions

Alkorta, Ibón; Blanco, Fernando; Elguero, José

doi:10.1016/j.tetlet.2008.09.131

Cited by 15 publications

(6 citation statements)

References 39 publications

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“…The hydrophobic benzyl group of benzyl alcohol will interact with the hydrophobic benzene ring of PDVB networks by hydrophobic interaction, whereas the hydrophilic alcoholic hydroxyl group of benzyl alcohol tends to interact the hydrophilic amide and amino groups of PADETA networks by hydrogen bonding . Moreover, π‐π stacking resulted from the benzene ring of benzyl alcohol and the pendant benzene ring of PDVB networks will contribute to enhance the swelling of PDVB/PADETA IPNs in benzyl alcohol as well . Therefore, the swelling ratio of PDVB/PADETA IPNs in benzyl alcohol is much higher than that in water and in toluene, which confirms that PDVB/PADETA IPNs has duple characters of hydrophobic and hydrophilic properties and it is a hydrophobic–hydrophilic IPNs.…”

Section: Resultsmentioning

confidence: 99%

Hydrophobic–hydrophilic polydivinylbenzene/polyacryldiethylenetriamine interpenetrating polymer networks and its adsorption performance toward salicylic acid from aqueous solutions

et al. 2014

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in Wiley Online Library (wileyonlinelibrary.com) Hydrophobic-hydrophilic interpenetrating polymer networks (IPNs) composed of polydivinylbenzene (PDVB) and polyacryldiethylenetriamine (PADETA) were prepared and its adsorption performance toward salicylic acid was studied from aqueous solutions. The structure of PDVB/PADETA IPNs was characterized by Fourier transform infrared spectroscopy, N 2 adsorption-desorption isotherms, weak basic exchange capacity, and swelling ratio, respectively. The results indicated that PDVB/PADETA IPNs possessed both hydrophobic and hydrophilic properties and they were much superior to the hydrophobic PDVB and the hydrophilic PADETA in adsorption of salicylic acid from aqueous solutions. The Freundlich model was more appropriate for fitting the equilibrium data than the Langmuir model and the isosteric enthalpy decreased with increment of the equilibrium uptakes. The breakthrough dynamic capacity of salicylic acid on PDVB/PADETA IPNs was 77.27 mg/mL wet resin at an initial concentration of 650.4 mg/L and a flow rate of 7.2 BV/h (bed volume, 1 BV 5 10 mL) and the saturated dynamic capacity was calculated to be 93.28 mg/mL wet resin. One hundred and forty milliliter of 0.01 mol/L of sodium hydroxide (w/v) and 40% of ethanol (v/v) could regenerate the resin column completely.

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Section: Resultsmentioning

confidence: 99%

Hydrophobic–hydrophilic polydivinylbenzene/polyacryldiethylenetriamine interpenetrating polymer networks and its adsorption performance toward salicylic acid from aqueous solutions

et al. 2014

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“…Yield: 75%. Anal 64. IR-ATR: ν(C=C) 1596, ν(C=N) 1514 cm −1 ; 1 H NMR: δ/ppm 1.17 (d, 3 J = 6.7 Hz, 12H, 4CH 3 ), 1.34 (d, 3 J = 6.7 Hz, 12H, 4CH 3 ), 3.25 (sept, 3 J = 6.7 Hz, 2H, SCH), 3.73 (sept, 3 J = 6.7 Hz, 2H, SCH), 7.14-7.42 (m, 16Har + 2HC=C), 7.69 (d, 3 J = 7.5 Hz, 4Har); 13 C{ 1 H} NMR: δ/ppm 22.8 (s, CH 3 ), 23.0 (s, CH 3 ), 37.9 (s, SCH), 38.6 (s, SCH), 128.2-132.4 (9s, Car + C=CH), 136.6 (s, C=CH), 139.2 (s, C=N).…”

Section: Synthesis Of [{Cu(µ-i)} 2 {Ph 2 C=n-ch=c(s-ipr) 2 }]mentioning

confidence: 99%

“…We recall briefly the main features of this theory. A topological analysis of electron density is a powerful tool for the study of different weak interatomic interactions (hydrogen bonding, [63] van der Waals, σ-π and π-π [64][65][66]) as well as for studying As a reference, the frontier MOs of 4-dichloro-2-aza-butadiene are presented as Figure S13 in the Supporting Material [7].…”

Section: Electronic Features and Aim Approachmentioning

confidence: 99%

4,4-Bis(isopropylthio)-1,1-diphenyl-2-azabuta-1,3-diene Adducts with Cadmium(II), Mercury(II) and Copper(I) Iodides: Crystal, Molecular and Electronic Structures of d10 Transition Metal Chelate Complexes

Kinghat,

Khatyr,

Knorr

et al. 2023

Chemistry

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The thioether-functionalized 2-azabutadiene (iPrS)2C=C(H)-N=CPh2 L ligates to CdI2 and HgI2 to form the chelate compounds [CdI2{(iPrS)2C=C(H)-N=CPh2] (1) and [HgI2(iPrS)2C=C(H)-N=CPh2] (2). Their crystal structures were solved via X-ray diffraction. Both crystallize in the non-centrosymmetric space groups: monoclinic P21 (1) and orthorhombic P212121 (2), respectively. The closed-shell d10 metal centers are four-coordinated (two iodides and S and N coordinating atoms from the ligand L) in both complexes. The geometrical indexes τ indicate that a highly distorted trigonal pyramidal is adopted for 1 and a seesaw geometry for 2. The comparative nature of metal–ligand bonds is discussed on the basis of metric parameters and of QT-AIM (quantum theory of atoms in molecules) calculations. L was also treated with CuI to obtain the dinuclear species [LCu(μ2-I2)CuL] (3), in which the two Cu(I) centers are linked by a short metal–metal bond. The geometric and electronic properties of 3 are compared with those of 1 and 2.

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“…Alkorta et al evaluated the p-p stacking by presence of bond critical points between the atoms of the aromatic rings in the syn conformed substituted 3,3-dimethyl-1,10-diphenyl-5,50-bis-1H-pyrazoles. 24 In the case of stacking DNA interactions, the Hobza group has carried out several important studies about the stability of the p complexes. 25 Matta et al 26 studied the properties of electron density of a CGCGAA TTCGCG dodecamer, from crystallographic geometries.…”

Section: Introductionmentioning

confidence: 99%

π-Stacking between Casiopeinas® and DNA bases

Galindo‐Murillo

Hernández-Lima

González-Rendón

et al. 2011

Phys. Chem. Chem. Phys.

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Casiopeínas® are copper complexes with the general formula [Cu(N-N)(N-O)]NO(3) and [Cu(N-N)(O-O)]NO(3) where N-N denotes a substituted bipyridine or phenanthroline, N-O indicates α-aminoacidate or peptide and O-O represents acetylacetonate or salicylaldehyde. This family of compounds has been evaluated in vitro and in vivo showing cytotoxic, genotoxic, and antineoplastic activity. The action mechanism is still not completely elucidated, but the possibility exists that these compounds interact with DNA by intercalation due to the aromatic moiety. In this work we found, using the properties of the electron density of a π-complex model base-Casiopeína®-base, that the stacking mechanism between Casiopeínas® and DNA bases is due to an electron density deficiency of the ligand of the Casiopeína® which is compensated for by an electron transfer from adenines by a π-π interaction.

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The use of a molecular balance derived from 5,5′-bipyrazole to calculate π−π stacking interactions

Cited by 15 publications

References 39 publications

Hydrophobic–hydrophilic polydivinylbenzene/polyacryldiethylenetriamine interpenetrating polymer networks and its adsorption performance toward salicylic acid from aqueous solutions

Hydrophobic–hydrophilic polydivinylbenzene/polyacryldiethylenetriamine interpenetrating polymer networks and its adsorption performance toward salicylic acid from aqueous solutions

4,4-Bis(isopropylthio)-1,1-diphenyl-2-azabuta-1,3-diene Adducts with Cadmium(II), Mercury(II) and Copper(I) Iodides: Crystal, Molecular and Electronic Structures of d10 Transition Metal Chelate Complexes

π-Stacking between Casiopeinas® and DNA bases

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