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Related Concept Videos

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...
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[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.
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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...
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...

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(1R*,2R*,4S*,5R*,6R*,8S*)-4,8-Dimethyl-2,6-diphenyl-bicyclo-[3.3.1]nonane-2,6-diol.

Vi T Nguyen1, Roger Bishop, Donald C Craig

  • 1School of Chemistry, University of New South Wales, Sydney 2052, Australia.

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

This study reveals the crystal structure of a racemic compound, C(23)H(28)O(2), highlighting its layered arrangement stabilized by hydrogen and C-H⋯π interactions. These interactions are crucial for understanding molecular packing in crystalline solids.

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Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Organic chemistry

Background:

  • Understanding intermolecular forces is key to predicting and controlling crystal structures.
  • Hydrogen bonding and van der Waals interactions significantly influence molecular packing and lattice stability.

Purpose of the Study:

  • To elucidate the crystal structure of the racemic title compound, C(23)H(28)O(2).
  • To analyze the intermolecular interactions, including hydrogen bonding and C-H⋯π interactions, that govern its solid-state arrangement.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of hydrogen bond networks and non-bonded contacts was performed.

Main Results:

  • The compound crystallizes in the C2/c space group, forming a layered structure.
  • A centrosymmetric three-hydrogen bond sequence links four molecules, with differential involvement of the hydroxy groups.
  • Edge-face interactions between aromatic rings and C-H⋯π interactions involving methyl and methylene groups stabilize the lattice.

Conclusions:

  • The crystal structure is characterized by a unique hydrogen bonding motif and significant π-π stacking interactions.
  • These interactions dictate the formation of a layered architecture and contribute to overall lattice stability.