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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

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 with both...
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...
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

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...
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

A neutral naphthalene diimide [2]rotaxane.

Henri-Pierre Jacquot de Rouville1, Julien Iehl, Carson J Bruns

  • 1Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, USA.

Organic Letters
|October 13, 2012
PubMed
Summary

Researchers synthesized a neutral donor-acceptor [2]rotaxane using click chemistry. X-ray crystallography revealed its solid-state structure, while NMR and electrochemistry explored its dynamic behavior and redox switching.

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
12:07

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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Rotaxanes are mechanically interlocked molecules with potential applications in molecular machines.
  • Donor-acceptor systems are crucial for charge transfer processes and molecular electronics.
  • Click chemistry offers efficient and reliable routes for synthesizing complex molecular architectures.

Purpose of the Study:

  • To synthesize and characterize a neutral donor-acceptor [2]rotaxane.
  • To elucidate the solid-state structure and superstructure of the synthesized rotaxane.
  • To investigate the dynamic behavior, geometrical reorganization, and redox-switching processes within the rotaxane.

Main Methods:

  • Synthesis of the [2]rotaxane using click chemistry.
  • X-ray crystallography for solid-state structure and superstructure determination.
  • Dynamic proton nuclear magnetic resonance ((1)H NMR) spectroscopy.
  • Electrochemical investigations (e.g., cyclic voltammetry).

Main Results:

  • Successful synthesis of a neutral donor-acceptor [2]rotaxane.
  • Detailed structural information obtained from X-ray crystallography, including packing arrangements.
  • NMR spectroscopy provided insights into molecular dynamics and conformational changes.
  • Electrochemical studies revealed redox-active properties and potential for switching.

Conclusions:

  • The study successfully synthesized and characterized a novel donor-acceptor [2]rotaxane.
  • The combination of structural and dynamic studies provides a comprehensive understanding of the molecule's behavior.
  • The findings contribute to the development of functional supramolecular systems for applications in molecular electronics and switches.