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Crown Ethers

Crown Ethers

Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules...

Physical Properties of Ethers

Physical Properties of Ethers

Overview
An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of alcohols of comparable molecular weight and slightly higher than those of hydrocarbons of comparable molecular weight (Table 1).
Ethers can act as hydrogen bond acceptors, making them more water-soluble than hydrocarbons, but since ethers cannot act as hydrogen bond donors, they are much less soluble in water than alcohols. Ethers are considered...

Unusual Results

Unusual Results

Unusual results are those that have a very low chance of occurring. Unusual results can be identified using probabilities and the range rule of thumb. In problems involving probability, unusual results can be observed in 2 instances – an unusually high number of successes or an unusually low number of successes.
According to the range rule of thumb, any value above or below two standard deviations, 2σ from the mean, μ is considered unusual.
Maximum unusual value =...

Solvents

Solvents

A solvent is a substance, most often a liquid, that can dissolve other substances. Here, the substance being dissolved is called a solute. When a solvent and a solute combine, they form a solution - a homogenous mixture of both the solvent and the solute. Water is a universal biological solvent. Its polar structure allows it to dissolve many other polar compounds. The ability of water to dissolve is governed by a balance between water molecules binding to each other and binding to the solute.
A...

Properties of Continuous Functions

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Continuous functions exhibit smooth, uninterrupted behavior, and combining them through standard operations retains this continuity. If f and g are continuous at a point a, then the functions f+g, f-g, cf (where c is a constant), fg, and fg (provided g(a)a) are also continuous at a. This allows the construction of complex functions from simpler continuous parts without losing smoothness.Polynomials, which are expressions formed by sums of powers of x with constant coefficients, are continuous...

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.

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Aromatically functionalized pseudo-crown ethers with unusual solvent response and enhanced binding properties.

Xiaoyu Xing¹, Yan Zhao

¹Department of Chemistry, Iowa State University, Ames, Iowa 50011-3111, USA. zhaoy@iastate.edu.

Organic & Biomolecular Chemistry

|February 16, 2018

Summary

Flexible pseudo-crown ethers show improved binding affinity and selectivity, even with compromised interactions in difficult solvents. This challenges the traditional view that host flexibility is always bad for binding.

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Area of Science:

Supramolecular Chemistry
Host-Guest Chemistry

Background:

Conformational flexibility in host molecules is typically viewed as a disadvantage for binding.
This flexibility can lead to entropic penalties and reduced binding affinity.

Purpose of the Study:

To investigate the binding properties of flexible pseudo-crown ethers.
To determine if host flexibility can enhance binding affinity and selectivity under certain conditions.

Main Methods:

Synthesis of flexible pseudo-crown ethers with terminal aromatic groups.
Binding studies using techniques like titration calorimetry and NMR spectroscopy.
Evaluation of binding in various solvent conditions, including those unfavorable for direct interactions.

Main Results:

Flexible pseudo-crown ethers demonstrated surprisingly enhanced binding affinity.
High selectivity was observed, particularly when direct binding interactions were weakened by solvent effects.
The aromatic end groups played a crucial role in mediating these enhanced interactions.

Conclusions:

Host conformational flexibility is not always detrimental and can be advantageous for binding.
Pseudo-crown ethers with specific structural features can overcome unfavorable solvent effects.
This work offers new design principles for host molecules in supramolecular chemistry.