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Related Concept Videos

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

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 Dienes01:16

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...
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Conformations of Butane02:20

Conformations of Butane

Unlike ethane and propane that have only two major conformations, butane has more than two conformers. The staggered form of butane in which the bulky methyl groups on the two carbons are placed on opposite sides, that is, at a dihedral angle of 180°, is the lowest energy, most stable form — called the anti conformer. This conformation is stabilized due to the absence of steric repulsion between the largely spaced out methyl groups. The other two staggered conformations are degenerate and have...
π Molecular Orbitals of 1,3-Butadiene01:24

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...
Structure and Nomenclature of Alcohols and Phenols02:23

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...

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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2,2,3,3-Tetra-fluoro-butane-1,4-diol.

Moritz M Reichvilser1, Felix W Roessner, Peter Klüfers

  • 1Ludwig-Maximilians-Universität, Department Chemie und Biochemie, Butenandtstrasse 5-13 (Haus D), 81377 München, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

This study reveals how hydrogen bonds in a fluorinated diol create layered structures. These findings advance our understanding of molecular self-assembly and crystal engineering.

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Last Updated: Jun 1, 2026

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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Area of Science:

  • Crystal engineering
  • Supramolecular chemistry
  • Fluorinated organic compounds

Background:

  • Hydrogen bonding plays a crucial role in the self-assembly of organic molecules.
  • Fluorinated compounds exhibit unique properties due to the high electronegativity of fluorine.
  • Understanding crystal structures informs material design and chemical synthesis.

Purpose of the Study:

  • To elucidate the crystal structure and intermolecular interactions of a partially fluorinated aliphatic diol.
  • To investigate the role of hydrogen bonding and other interactions in forming extended networks.
  • To provide insights into the structural characteristics of fluorinated diols.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
  • Analysis of intermolecular interactions, including hydrogen bonds (O-H⋯O) and C-H⋯F interactions.
  • Topological analysis of the hydrogen bond network to identify ring and chain motifs.

Main Results:

  • The compound, C(4)H(6)F(4)O(2), exhibits a partially fluorinated aliphatic diol structure.
  • Cooperative O-H⋯O hydrogen bonds form characteristic R(2)(2)(14) rings.
  • These rings are interconnected into infinite 2D layers parallel to the (100) crystallographic plane via C(7) chains.
  • A notable C-H⋯F interaction was also identified within the crystal lattice.

Conclusions:

  • The crystal structure is dominated by a robust hydrogen bonding network leading to layered architecture.
  • The identified R(2)(2)(14) rings and C(7) chains dictate the formation of 2D supramolecular layers.
  • The presence of C-H⋯F interactions contributes to the overall structural stability and packing.
  • This study enhances the understanding of structure-property relationships in fluorinated organic materials.