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Related Concept Videos

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

1.7K
In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
1.7K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.5K
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...
3.5K
Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

7.7K
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...
7.7K
NMR Spectroscopy of Aromatic Compounds01:14

NMR Spectroscopy of Aromatic Compounds

4.7K
Aromatic compounds can be identified or analyzed using proton NMR and carbon‐13 NMR. Typically, aromatic hydrogens or hydrogens directly bonded to the aromatic rings are strongly deshielded by the aromatic ring current. Therefore, they absorb in the range of 6.5–8.0 ppm in proton NMR spectra. For instance, aromatic hydrogens directly bonded to the benzene ring absorb at 7.3 ppm. However, aromatic hydrogens of larger rings absorb farther upfield or downfield than the ideal range.
4.7K
Spin–Spin Coupling: One-Bond Coupling01:17

Spin–Spin Coupling: One-Bond Coupling

1.2K
Coupling interactions are strongest between NMR-active nuclei bonded to each other, where spin information can be transmitted directly through the pair of bonding electrons. While nuclei polarize their electrons to the opposite spins, the bonding electron pair has opposite spins. Configurations with antiparallel nuclear spins are expected to be lower in energy. When coupling makes antiparallel states more favorable, J is considered to have a positive value. The one-bond coupling constant, 1J,...
1.2K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

3.3K
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.
3.3K

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Orientational Transition in a Liquid Crystal Triggered by the Thermodynamic Growth of Interfacial Wetting Sheets
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Aromaticity decreases single-molecule junction conductance.

Wenbo Chen1, Haixing Li, Jonathan R Widawsky

  • 1Department of Chemistry, Columbia University , New York, New York 10027, United States.

Journal of the American Chemical Society
|January 9, 2014
PubMed
Summary
This summary is machine-generated.

Molecular wire conductance decreases with increased aromaticity in five-membered rings. Nonaromatic cyclopentadiene wires show higher electrical conductance than aromatic furan and thiophene wires.

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Area of Science:

  • Molecular electronics
  • Organic chemistry
  • Condensed matter physics

Background:

  • Single-molecule electronics offers precise control over charge transport.
  • Understanding structure-property relationships in molecular wires is crucial for device design.

Purpose of the Study:

  • To investigate the relationship between the aromaticity of cyclic five-membered rings in molecular wires and their electrical conductance.
  • To determine how molecular structure influences charge transport at the single-molecule level.

Main Methods:

  • Utilizing the scanning tunneling microscope-based break-junction technique to form and measure single-molecule junctions.
  • Synthesizing and testing molecular wires incorporating cyclopentadiene, furan, and thiophene rings.

Main Results:

  • Single-molecule conductance was measured for wires containing cyclopentadiene, furan, and thiophene.
  • A negative correlation was observed between the resonance energy (aromaticity) of the five-membered ring and the measured conductance.
  • Nonaromatic cyclopentadiene derivatives exhibited higher conductance than aromatic furan and thiophene derivatives.
  • Conductance of furan-based wires was consistently higher than analogous thiophene systems, confirming the robustness of the observed trend.

Conclusions:

  • The aromaticity of the molecular backbone significantly impacts single-molecule conductance.
  • Lower aromaticity, particularly structures favoring a quinoid form, leads to higher conductance.
  • The findings suggest that molecular design strategies should consider minimizing aromatic stabilization to enhance conductivity in molecular wires.