Solvent Effects on Hydrogen Bonding

Cook, Joanne; Hunter, Christopher A.; Low, Caroline M. R.; Perez‐Velasco, Alejandro; Vinter, Jeremy G.

doi:10.1002/anie.200604966

Cited by 199 publications

(222 citation statements)

References 33 publications

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“…The solvent dependence of the dynamic behaviour of 1 can be rationalized in terms of the ability of the NH proton to engage in hydrogen bonding with a suitable acceptor. [31,47,48] DMSO is expected to be a better hydrogenbond acceptor than acetone, [49] and association between 1 and the solvent will result in steric hindrance that will slow down the rate of rotation about C py -N imine bond. The hydrogen bonding capacity of the imine NH in 1 is apparent in its packing in the solid state (Figure 8), and this observation is in line with the results of several studies of phenylhydrazones which conclude that such hydrogen bonding is the predominant factor is determining solid state conformation and solution dynamic behaviour.…”

Section: Solution Behaviourmentioning

confidence: 99%

4′‐Hydrazone Derivatives of 2,2′:6′,2"‐Terpyridine: Protonation and Substituent Effects

et al. 2008

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Four 4′‐hydrazone derivatives of 2,2′:6′,2"‐terpyridine which vary in their N‐ and C‐substitution in the R′NN=CRPh unit have been prepared and structurally characterized. Protonation studies and solution behaviour of these compounds are described, as well as representative crystal structures of mono‐ and diprotonated derivatives. In the solid‐state structures of each neutral compound, the tpy domain adopts the anticipated trans,trans‐conformation, and intramolecular steric factors compete with π‐stacking effects to control the amount to which the C‐phenyl substituent twists out of the plane of the tpy unit. When R′ = H, the imine NH group engages in hydrogen bonding interactions in the solid state, except where R = Ph. In solution, variable temperature 1H NMR spectroscopy shows that on going from R = Me to Ph (with R′ = H), the barrier to rotation about the Cpy–Nimine bond increases; with R = R′ = H, the hydrogen bonding capabilities of the solvent to the imine NH influence this dynamic process. In the N‐methyl derivative (R = H and R′ = Me), rotation about the Cpy–Nimine bond is facile at room temperature. Protonation of the derivative with R = R′ = H results in an increase in the activation barrier to rotation, consistent with a greater π‐contribution to the Cpy–Nimine bond. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Section: Solution Behaviourmentioning

confidence: 99%

4′‐Hydrazone Derivatives of 2,2′:6′,2"‐Terpyridine: Protonation and Substituent Effects

et al. 2008

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“…Monomer 5 was used as the binding monomer and EGDMA as cross-linking monomer. Based on the solubility tests of the templates (≤100 mM) (see Electronic Supplementary Material Table S1) and that of 5, we selected chloroform as a non-polar and H-bond stabilising solvent and porogen [30]. Modifying the length of acyl group will increase the hydrophobic character of the templates from 2<3<4 and induce potentially different hydrophobic interactions into the template cavity.…”

Section: Polymer Preparationmentioning

confidence: 99%

Evaluation of molecularly imprinted polymers using 2′,3′,5′-tri-O-acyluridines as templates for pyrimidine nucleoside recognition

et al. 2014

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In this paper, we describe the synthesis and evaluation of molecularly imprinted polymers (MIPs), prepared using 2',3',5'-tri-O-acyluridines as 'dummy' templates, for the selective recognition of uridine nucleosides. The MIPs were synthesised using a non-covalent approach with 2,6-bis-acrylamidopyridine (BAAPy) acting as the binding monomer and ethylene glycol dimethacrylate (EGDMA) as the cross-linking agent. The MIPs were evaluated in terms of capacity, selectivity and specificity by analytical and frontal liquid chromatography measurements. The results obtained in organic mobile phases suggest that the nucleosides are specifically bound to the polymer by the complementary hydrogen bonding motifs of the binding monomer and the nucleoside bases. The MIPs exhibited relatively high imprinting factors for 2',3',5'-tri-O-acyluridines, while they did not show any binding capacity for other nucleosides lacking the imide moiety on their base. Moreover, the presence of ester-COO groups in the EGDMA cross-linker may lead to the formation of additional hydrogen bonds with the 2',3' and/or 5'-OH of sugar part, allowing enhancement of the recognition of the uridine nucleosides. In aqueous media, results show that the binding is driven by hydrophobic interactions.

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“…[385] Für ein Assoziat aus Perfluor-tert-butanol und Tri-n-butylphosphinoxid wurde bei Anwendung neu abgeleiteter a-und b-Faktoren die in Abbildung S14 gezeigte lineare Korrelation gefunden, wenn von den a-und b-Werten der verwendeten Substrate die a s -und b s -Werte des jeweiliSupramolekulare Komplexe Angewandte Chemie gen Mediums abgezogen wurden. [387] Die geringe Streuung ist die Konsequenz der hier verwendeten speziellen a s -und b sWerte, die mit den gleichen Substraten wie die bei der Korrelation selber erhalten wurden.…”

Section: Wasserstoffbrücken Für Die Komplexierung Von Anionen Mit Amiunclassified

Bindungsmechanismen in supramolekularen Komplexen

Schneider

2009

Angewandte Chemie

185

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Kräfte‐Sammelsurium: Supramolekulare Komplexe, wie der gezeigte, beruhen meist auf einer Kombination unterschiedlichster Wechselwirkungen, wie Ionenpaarbildung, Wasserstoffbrücken und Stapelwechselwirkungen. Die nicht immer einfache Charakterisierung von Natur und Stärke der intermolekularen Kräfte liefert Beiträge zum Verständnis biomimetischer Systeme wie auch zum Design von synthetischen Rezeptoren, Wirkstoffen und intelligenten Materialien. Die supramolekulare Chemie hat in den letzten Jahren eine enorme Ausdehnung erfahren, sowohl mit Blick auf mögliche Anwendungen wie auch auf analoge biologische Systeme. Bildung und Funktion supramolekularer Komplexe werden durch eine Vielzahl von oft schwer zu differenzierenden nichtkovalenten Kräften bestimmt. Ziel dieses Aufsatzes ist es, die entscheidenden Wechselwirkungsmechanismen zusammenhängend darzustellen und das Gesamtgebiet auf diese Weise zu klassifizieren. Als Beispiele werden meist organische Wirt‐Gast‐Komplexe gewählt, unter Berücksichtigung auch von biologisch relevanten Fragestellungen. Das Verständnis und die Quantifizierung der intermolekularen Wechselwirkungen ist für die rationale Planung neuer supramolekularer Systeme, einschließlich intelligenter Materialien, ebenso von Bedeutung wie für die Entwicklung neuer Wirkstoffe.

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Solvent Effects on Hydrogen Bonding

Cited by 199 publications

References 33 publications

4′‐Hydrazone Derivatives of 2,2′:6′,2"‐Terpyridine: Protonation and Substituent Effects

4′‐Hydrazone Derivatives of 2,2′:6′,2"‐Terpyridine: Protonation and Substituent Effects

Evaluation of molecularly imprinted polymers using 2′,3′,5′-tri-O-acyluridines as templates for pyrimidine nucleoside recognition

Bindungsmechanismen in supramolekularen Komplexen

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