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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...

IUPAC Nomenclature of Aldehydes

IUPAC Nomenclature of Aldehydes

Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...

Benzene to Phenol via Cumene: Hock Process

Benzene to Phenol via Cumene: Hock Process

The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene hydroperoxide...

Five-Membered Heterocyclic Aromatic Compounds: Overview

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.

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.

Carbocations

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...

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Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines

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|May 17, 2012

Summary

This study details the crystal structure of a molecule C(10)H(8)N(2)O, revealing specific ring interactions and hydrogen bonds. These molecular interactions form supramolecular layers, offering insights into crystal engineering.

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Area of Science:

Crystallography
Organic Chemistry
Supramolecular Chemistry

Background:

Understanding molecular interactions is crucial for designing materials with specific properties.
Crystal structure analysis provides detailed information on atomic arrangements and intermolecular forces.

Purpose of the Study:

To elucidate the crystal structure of the molecule C(10)H(8)N(2)O.
To investigate the intermolecular interactions governing crystal packing and supramolecular assembly.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of bond lengths, bond angles, torsion angles, and non-covalent interactions (hydrogen bonds, π-π stacking).

Main Results:

The molecule C(10)H(8)N(2)O exhibits a dihedral angle of 10.14° between its five- and six-membered rings.
The aldehyde group is nearly coplanar with the pyrazole ring (torsion angle -179.35°).
Inversion dimers are formed via C-H⋯O interactions, and these dimers assemble into supramolecular layers through C-H⋯π and π-π interactions.

Conclusions:

The crystal structure is stabilized by a combination of hydrogen bonding and π-π stacking interactions.
The identified intermolecular interactions dictate the formation of supramolecular layers, providing a blueprint for crystal engineering.