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Related Concept Videos

Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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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...
3.1K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

3.0K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
3.0K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.1K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
3.1K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

11.5K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as...
11.5K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

13.3K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
13.3K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.5K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Aromaticity effect on supramolecular aggregation. Aromatic vs. cyclic monohydroxy alcohols.

N Soszka1, B Hachuła2, M Tarnacka3

  • 1Institute of Chemistry, Faculty of Science and Technology, University of Silesia in Katowice, Szkolna 9, 40-006 Katowice, Poland; Institute of Physics, Faculty of Science and Technology, University of Silesia in Katowice, 75 Pułku Piechoty 1, 41-500 Chorzów, Poland.

Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
|April 16, 2022
PubMed
Summary

The aromatic phenyl ring has a greater steric effect on alcohol self-assembly than the cyclic cyclohexyl ring, influencing molecular organization and dynamics. This impacts hydrogen bonding and supramolecular structures.

Keywords:
AromaticityCyclohexyl alcoholsPhenyl alcoholsSelf-associationSteric hindrance

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Area of Science:

  • Physical Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Understanding molecular self-assembly is crucial for designing materials with specific properties.
  • Steric hindrance plays a significant role in dictating the organization and interactions of molecules.

Purpose of the Study:

  • To investigate the steric hindrance effect of cyclic (cyclohexyl) versus aromatic (phenyl) rings on the self-association of monohydroxy alcohols (MAs).
  • To compare the impact of these rings on molecular organization, hydrogen bonding, and dynamics.

Main Methods:

  • X-Ray Diffraction (XRD)
  • Differential Scanning Calorimetry (DSC)
  • Fourier Transform Infrared (FTIR) spectroscopy
  • Broadband Dielectric Spectroscopy (BDS)
  • Pendant Drop (PD) methods

Main Results:

  • Phenyl alcohol (PhA) derivatives showed greater differences in association degree, dissociation energy, and nanoassociate homogeneity compared to cyclohexyl alcohol (CA) derivatives.
  • XRD data indicated phenyl groups induce more molecular heterogeneity than cyclohexyl groups.
  • Molecular dynamics and Kirkwood factors differed, with CAs showing slightly higher long-range dipole correlations.
  • Unexpectedly, PhA surface layers were more organized than CA surface layers.

Conclusions:

  • The phenyl ring exerts a stronger steric impact on alcohol self-assembly than the cyclohexyl ring.
  • Aromaticity significantly influences H-bonding patterns, supramolecular structure, and intermolecular dynamics.
  • These findings offer insights into structure-property relationships in alcohols based on ring structure.