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π Molecular Orbitals of 1,3-Butadiene

π Molecular Orbitals of 1,3-Butadiene

Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic 1,2- and 1,4-Addition of X₂ to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.

Structure of Conjugated Dienes

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

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Related Experiment Video

Updated: Jun 1, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

1,4-Diphenyl-butane-1,4-dione.

¹School of Chemical and Materials Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study details the crystal structure of C(16)H(14)O(2), revealing a molecule with two benzene rings. These rings are positioned at a specific dihedral angle, indicating a unique molecular geometry.

Area of Science:

Crystallography
Organic Chemistry
Molecular Structure

Background:

Understanding molecular geometry is crucial in organic chemistry.
Crystallographic studies provide precise structural information.
The compound C(16)H(14)O(2) was synthesized for structural analysis.

Purpose of the Study:

To determine the precise three-dimensional structure of C(16)H(14)O(2).
To analyze the spatial arrangement of the benzene rings within the molecule.
To characterize the crystallographic properties of the title compound.

Main Methods:

Single-crystal X-ray diffraction was employed.
The crystal structure was solved and refined.
The molecular geometry and packing were analyzed.

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Main Results:

The asymmetric unit contains one half-molecule of C(16)H(14)O(2) located on a twofold rotation axis.
The two benzene rings exhibit a dihedral angle of 72.28(2)°.
Detailed crystallographic data were obtained.

Conclusions:

The study provides a definitive crystal structure for C(16)H(14)O(2).
The observed dihedral angle offers insights into the molecule's conformation.
This structural data can inform future research in organic synthesis and materials science.