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Physical Properties of Alcohols and Phenols

Physical Properties of Alcohols and Phenols

Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
Alcohols possess a higher boiling point than aliphatic hydrocarbons of similar...

Structure and Nomenclature of Alcohols and Phenols

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...

Acidity and Basicity of Alcohols and Phenols

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.

Ionic Crystal Structures

Ionic Crystal Structures

Ionic crystals consist of two or more different kinds of ions that usually have different sizes. The packing of these ions into a crystal structure is more complex than the packing of metal atoms that are the same size.
Most monatomic ions behave as charged spheres, and their attraction for ions of opposite charge is the same in every direction. Consequently, stable structures for ionic compounds result (1) when ions of one charge are surrounded by as many ions as possible of the opposite...

Aldehydes and Ketones with Water: Hydrate Formation

Aldehydes and Ketones with Water: Hydrate Formation

An oxygen-based nucleophile, like water, can undergo addition reactions with aldehydes and ketones. The reaction leads to the formation of hydrates, also referred to as 1,1-diols or geminal diols.
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

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Hydrogen-bonded complexes between 4-alkoxystilbazoles and fluorophenols: solid-state structures and liquid

Joanna P-W Wong¹, Adrian C Whitwood, Duncan W Bruce

¹Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|October 23, 2012

Summary

New hydrogen-bonded complexes of fluorophenols and alkoxystilbazoles exhibit liquid-crystal properties. Intramolecular hydrogen bonding influences mesophase stability, with 2-fluoro substitution enhancing stability.

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Area of Science:

Supramolecular Chemistry
Materials Science
Crystallography

Background:

Hydrogen-bonded complexes are crucial in supramolecular chemistry.
Fluorophenols and alkoxystilbazoles are key components for creating novel materials.
Understanding structure-property relationships in these complexes is vital for materials design.

Purpose of the Study:

To synthesize and characterize new hydrogen-bonded complexes.
To investigate the liquid-crystalline properties of these novel complexes.
To correlate the structural features with observed mesophase behavior.

Main Methods:

Synthesis of 48 new hydrogen-bonded complexes.
Single-crystal X-ray diffraction for structural analysis of 10 complexes.
Polarized optical microscopy and differential scanning calorimetry for liquid crystal phase characterization.

Main Results:

40 of the 48 complexes displayed liquid-crystal properties.
Butyloxystilbazole complexes were nematic; dodecyloxystilbazole complexes were smectic A (SmA).
Octyloxystilbazole complexes showed a mixture of nematic and SmA phases.
Complexes with 2-fluorophenols exhibited the most stable mesophases due to intramolecular hydrogen bonding, forming stable, coplanar conformations.

Conclusions:

The study successfully prepared and characterized novel hydrogen-bonded complexes.
Liquid crystal phase behavior is strongly influenced by the alkyl chain length of the alkoxystilbazole.
Intramolecular hydrogen bonding, particularly with 2-fluoro substitution, significantly enhances mesophase stability and influences molecular conformation.