Hydrogen Bond Formation with Saturated Cyclic Ethers<sup>1</sup>

Searles, Scott; Tamres, Milton

doi:10.1021/ja01152a041

Cited by 142 publications

(40 citation statements)

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“…It has been suggested [51] that the presence of two oxygen atoms strengthens the interaction between adjacent molecules, leading to a more condensed structure. It is also noticeable that due to its ability to form unusual symmetrical hydrogen bonded structures, the cyclic ether 1,4-dioxane presents high water solubility and a remarkable capacity to solvate ions [53]. Furthermore, it shows a relatively strong quadrupolar moment, which could lead important repercussions in the behaviour of its mixtures.…”

Section: Resultsmentioning

confidence: 99%

“…Several studies have highlighted differences in this capacity showing that monoethers tetrahydrofuran, or tetrahydropyran are stronger donors than cyclic diethers 1,3-dioxolane and 1,4-dioxane. Founded on calorimetric and spectroscopic data, a sequence tetrahydrofuran > tetrahydropyran > 1,3-dioxolane > 1,4-dioxane has been presented in terms of their electron donor ability [53][54][55].…”

Section: Resultsmentioning

confidence: 99%

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Isothermal (vapour+liquid) equilibrium of (cyclic ethers+ chlorohexane) mixtures: Experimental results and SAFT modelling

Bandrés

Giner

López

et al. 2008

The Journal of Chemical Thermodynamics

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Isothermal (vapour+liquid) equilibrium of (cyclic ethers+ chlorohexane) mixtures: Experimental results and SAFT modelling

Bandrés

Giner

López

et al. 2008

The Journal of Chemical Thermodynamics

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“…The HB strength of oxygen in ether (Motoyama et al 1967), and nitrogen in pyridine and 2-chloropyridine (Percampus et al 1968) is as follows: pyridine > ether, 2-chloropyridine, as evaluated in terms of HB formation with methanol. However, the oxygens in cyclic ethers are stronger HB acceptors than corresponding acyclic ethers (Searles and Tamres 1951) as indicated by much higher water solubility of tetrahydrofuran compared with diethyl ether. Such particular HB forming ability of the oxygen combined with the non-aromatic feature of the tetrahydrofuran ring should differentiate dinotefuran from other neonicotinoids in the mode of nAChR activation and possibly, in the sensitivity to nAChR-based resistance (Liu et al 2006).…”

Section: The Third Hb Bondmentioning

confidence: 99%

A hypothesis to account for the selective and diverse actions of neonicotinoid insecticides at their molecular targets, nicotinic acetylcholine receptors: catch and release in hydrogen bond networks

et al. 2007

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The low mammalian toxicity of neonicotinoid insecticides has been shown to be attributable, at least in part, to their selective actions on insect nicotinic acetylcholine receptors (nAChRs). There are multiple nAChRs in insects and a wealth of neonicotinoid chemicals. Studies to date have discribed a wide range of effects on nAChRs, notably partial agonist, super agonist and antagonist actions. Both the diversity of the neonicotinoid actions and their selectivity for insect over vertebrate nAChRs are the result of physicochemical and steric interactions at their molecular targets (nAChRs). In such interactions, the formation and breakage of hydrogen bond (HB) networks plays a key role. Therefore the loss or gain of even a single HB resulting from either structural changes in neonicotinoids, or the amino acid sequence of a particular nAChR subunit, could result in a drastic modification of neonicotinoid actions. In addition to the amino acid residues, the backbone carbonyl of nAChRs may also be involved in the formation of HB networks with neonicotinoids.

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“…1 in terms of an equilibrium with only a 1:l complex has been attempted but did not lead to satisfactory results. lLIeasurements on the heat of mixing (25) of chloroform in dioxane also support the existence of the 2 : l complex.…”

Section: Chlorofor+n Dilution Shiftmentioning

confidence: 75%

Solvent Shift of the Chloroform Nuclear Magnetic Resonance Line

Kaiser¹

1963

Can. J. Chem.

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The chloroforin and dioxane proton magnetic resonance line positions have been measured relative to a n internal tetramethylsilane reference signal as a function of concentratioll in binary chloroform -1,4-dioxane mixtures a t 28' C. Corrections have been applied to eliminate the effects of the chloroform self-association and of the non-specific interactions of the chloroform dipole. Analysis of the remaining nuclear magnetic resonance line shift In terms of an equilibrium between free chloroform and 1:1 and 2:l chlorofornl-dioxane complexes gives the position of the signal from chloroforin in the 1:l coi~lplex a t -1.20 p.p.m. and in the 3:l complex a t -0.85 p.p.m. relative to the position of the signal from chloroform a t infinite dilution in cyclohexane. Data on other binary chloroform systems have been collected from the literature and have been similarly corrected. The results support the hypothesis of a monotonic relation between the proton magnetic resonance line shift and the energy of the hydrogen bonds which are believed to cause the formation of complexes in these systems. The accuracy of the data is not sufficient to give conclusive e\ideilce regarding the linearity of this relation or the structure of the 2:l chloroform-dioxane complex. INTRODUCTIOS

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Hydrogen Bond Formation with Saturated Cyclic Ethers¹

Cited by 142 publications

References 0 publications

Isothermal (vapour+liquid) equilibrium of (cyclic ethers+ chlorohexane) mixtures: Experimental results and SAFT modelling

Isothermal (vapour+liquid) equilibrium of (cyclic ethers+ chlorohexane) mixtures: Experimental results and SAFT modelling

A hypothesis to account for the selective and diverse actions of neonicotinoid insecticides at their molecular targets, nicotinic acetylcholine receptors: catch and release in hydrogen bond networks

Solvent Shift of the Chloroform Nuclear Magnetic Resonance Line

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Hydrogen Bond Formation with Saturated Cyclic Ethers1

Cited by 142 publications

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Isothermal (vapour+liquid) equilibrium of (cyclic ethers+ chlorohexane) mixtures: Experimental results and SAFT modelling

Isothermal (vapour+liquid) equilibrium of (cyclic ethers+ chlorohexane) mixtures: Experimental results and SAFT modelling

A hypothesis to account for the selective and diverse actions of neonicotinoid insecticides at their molecular targets, nicotinic acetylcholine receptors: catch and release in hydrogen bond networks

Solvent Shift of the Chloroform Nuclear Magnetic Resonance Line

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Hydrogen Bond Formation with Saturated Cyclic Ethers¹