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Related Concept Videos

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

8.0K
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...
8.0K
Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

8.4K
The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
8.4K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.4K
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...
4.4K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

7.2K
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
7.2K
Molecular Shape and Polarity03:37

Molecular Shape and Polarity

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Dipole Moment of a Molecule
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Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

7.2K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
7.2K

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F&#246;rster Resonance Energy Transfer Mapping: A New Methodology to Elucidate Global Structural Features
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Aromatic donor-acceptor interactions in non-polar environments.

Giles M Prentice1, Sofia I Pascu, Sorin V Filip

  • 1Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UK. g.d.pantos@bath.ac.uk.

Chemical Communications (Cambridge, England)
|April 16, 2015
PubMed
Summary
This summary is machine-generated.

Aromatic donor-acceptor interactions between dialkyl naphthalenediimide and dialkoxynaphthalene are strong enough in non-polar solvents like heptane to create supramolecular assemblies. This finding is crucial for designing novel self-assembling materials.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Aromatic donor-acceptor interactions are fundamental in supramolecular chemistry.
  • Understanding these interactions in non-polar environments is key for designing self-assembling systems.
  • Dialkyl naphthalenediimide and dialkoxynaphthalene are relevant building blocks for such systems.

Purpose of the Study:

  • To quantify the strength of aromatic donor-acceptor interactions between dialkyl naphthalenediimide and dialkoxynaphthalene.
  • To investigate the influence of non-polar environments on these interactions.
  • To determine if these interactions can drive the formation of supramolecular assemblies.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy, specifically (1)H NMR, was employed.
  • UV-vis spectroscopy was utilized for characterization.
  • Isothermal titration calorimetry (ITC) was performed to measure binding thermodynamics.

Main Results:

  • The strength of donor-acceptor interactions was successfully evaluated.
  • These interactions were found to be significant in non-polar solvents.
  • UV-vis and ITC data confirmed the formation of stable complexes.

Conclusions:

  • Aromatic donor-acceptor interactions between the studied molecules are sufficiently strong in heptane.
  • These interactions are capable of driving the formation of supramolecular assemblies in aliphatic solvents.
  • The findings provide insights into the design principles for self-assembling organic materials.