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Aromatic Hydrocarbon Cations: Structural Overview

Aromatic Hydrocarbon Cations: Structural Overview

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...

Stability of Substituted Cyclohexanes

Stability of Substituted Cyclohexanes

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...

Aromatic Hydrocarbon Anions: Structural Overview

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...

Frost Circles for Different Conjugated Systems

Frost Circles for Different Conjugated Systems

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.

Photochemical Electrocyclic Reactions: Stereochemistry

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation

Conformations of Cyclohexane

Conformations of Cyclohexane

Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...

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Related Experiment Video

Updated: May 13, 2025

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

Chlorocyclohexane Valence and Rydberg Electronic Excitations.

E Bandeira¹, S Kumar^2,3, A S Barbosa¹

¹Departamento de Física, Universidade Federal do Paraná, Caixa Postal 19044, Curitiba, Paraná 81531-980, Brazil.

The Journal of Physical Chemistry. A

|April 16, 2025

Summary

This summary is machine-generated.

New measurements of chlorocyclohexane photoabsorption reveal its atmospheric behavior. Solar photolysis is a significant sink only above 20 km, impacting atmospheric chemistry models.

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Area of Science:

Atmospheric Chemistry
Photophysics
Quantum Chemistry

Background:

Chlorocyclohexane (C6H11Cl) is a molecule of interest in atmospheric studies.
Understanding its photoabsorption cross-sections is crucial for atmospheric fate assessments.

Purpose of the Study:

To determine new cross-section values for chlorocyclohexane photoabsorption.
To interpret the photoabsorption spectrum using theoretical calculations.
To estimate photolysis lifetimes and assess its role as an atmospheric sink.

Main Methods:

Vacuum ultraviolet (VUV) photoabsorption measurements (5.0-10.8 eV).
Theoretical calculations using time-dependent density functional theory (TD-DFT).
Assignment of excited states and spectral features.

Main Results:

New cross-section values for C6H11Cl were obtained.
Excited states were assigned to valence, mixed valence-Rydberg, and Rydberg transitions.
Specific vibrational modes were linked to spectral features.
Photolysis lifetimes indicate solar photolysis is a relevant sink only above 20 km altitude.

Conclusions:

The study provides critical data for atmospheric modeling of chlorocyclohexane.
Predissociative character plays a significant role in the molecule's electronic states.
Solar photolysis is a minor sink for chlorocyclohexane in the lower atmosphere.