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NMR Spectroscopy of Benzene Derivatives

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...

Structure of Benzene: Molecular Orbital Model

Structure of Benzene: Molecular Orbital Model

According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

Directing and Steric Effects in Disubstituted Benzene Derivatives

Directing and Steric Effects in Disubstituted Benzene Derivatives

When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the...

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...

Spin–Spin Coupling Constant: Overview

Spin–Spin Coupling Constant: Overview

In bromoethane, the three methyl protons are coupled to the two methylene protons that are three bonds away. In accordance with the n+1 rule, the signal from the methyl protons is split into three peaks with 1:2:1 relative intensities. The methylene protons appear as a quartet, with the relative intensities of 1:3:3:1.
Qualitatively, any spin plus-half nucleus polarizes the spins of its electrons to the minus-half state. Consequently, the paired electron in the hydrogen–carbon bond must...

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Scalable Quantum Integrated Circuits on Superconducting Two-Dimensional Electron Gas Platform

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Constructive Quantum Interference in Single-Molecule Benzodichalcogenophene Junctions.

Masoud Baghernejad^1,2, Yang Yang¹, Oday A Al-Owaedi³

¹State Key Laboratory of Physical Chemistry of Solid Surfaces, Pen-Tung Sah Institute of Micro-Nano Science and Technology, College of Chemistry and Chemical Engineering, iChEM, Xiamen University, 361005, Xiamen, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|February 6, 2020

Summary

This summary is machine-generated.

This study explores heteroatom substitution in non-alternant hydrocarbons, finding constructive quantum interference (CQI) persists despite conductivity changes. Sulfur and oxygen substitution in benzodichalcogenophene molecules demonstrates CQI resilience.

Keywords:

density functional calculations perturbation theory quantum interference scanning tunneling microscopy single-molecule conductors

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Area of Science:

Organic Chemistry
Materials Science
Quantum Chemistry

Background:

Heteroatom substitution in alternant hydrocarbons is a known method for tuning electrical conductance.
Non-alternant hydrocarbons with odd-membered rings offer a new platform for investigating electronic properties.
Benzodichalcogenophene (BDC) compounds, with fused five- and six-membered rings, are promising π-conjugated systems.

Purpose of the Study:

To examine the effect of heteroatom substitution (sulfur and oxygen) on the electrical conductance of non-alternant hydrocarbons.
To investigate the sensitivity and resilience of constructive quantum interference (CQI) in these molecular cores.
To compare the conductances of symmetric and asymmetric BDC derivatives.

Main Methods:

Synthesis and characterization of two C2-symmetric (I and II) and one asymmetric (III) benzodichalcogenophene molecules.
Incorporation of sulfur (S) and oxygen (O) heteroatoms into the five-membered rings of the BDC cores.
Measurement and analysis of electrical conductances of the synthesized molecules.

Main Results:

Differences in conductance were observed, primarily attributed to S-C and O-C bond lengths and altered resonance integrals.
The asymmetric molecule (III) exhibited significantly lower conductance compared to the symmetric molecules (I and II).
Constructive quantum interference (CQI) was found to be resilient and present in all investigated molecules, regardless of heteroatom type or molecular symmetry.

Conclusions:

Heteroatom substitution in non-alternant BDC cores does not disrupt constructive quantum interference (CQI).
CQI resilience is a key feature in these π-conjugated systems, offering pathways for designing novel electronic materials.
The study highlights the potential of BDC derivatives for applications in molecular electronics.