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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 with both...

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

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 annulenes. In...

π Electron Effects on Chemical Shift: Overview

π Electron Effects on Chemical Shift: Overview

An applied magnetic field causes loosely bound π-electrons in organic molecules to circulate, producing a local or induced diamagnetic field over a large spatial volume. As the molecules tumble in solution, the field generated by π-electrons in spherical substituents results in a zero net field. However, the net field generated by π-electrons in non-spherical substituents is not zero. The effect of this induced field depends on the orientation of the molecule with respect to B0, resulting 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 overlap of p...

Complexation Equilibria: Factors Influencing Stability of Complexes

Complexation Equilibria: Factors Influencing Stability of Complexes

In complexation reactions, metal cations are the electron pair acceptors, and the ligands are the electron pair donors. The stability of the metal complexes depends primarily on the complexing ability of the central metal ion and the nature of the ligands. Generally, the complexing ability of the metal ion depends on the size and charge of the ion. As the metal ion size increases, the stability of the metal complexes decreases, provided that the valency of the metal ion and the ligands remain...

Cationic Chain-Growth Polymerization: Mechanism

Cationic Chain-Growth Polymerization: Mechanism

The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...

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Updated: May 14, 2026

Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance

Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance

Published on: September 5, 2018

Charged and metallic molecular monolayers through surface-induced aromatic stabilization.

G Heimel¹, S Duhm, I Salzmann

¹Institut für Physik, Humboldt-Universität zu Berlin, Brook-Taylor-Straße 6, D-12489 Berlin, Germany. georg.heimel@physik.hu-berlin.de

Nature Chemistry

|February 21, 2013

Summary

Organic semiconductors can become metallic on metal surfaces. This occurs when molecule-surface bonding enhances conjugation, reducing the electronic gap and creating metallic molecular monolayers for surface engineering.

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Area of Science:

Materials Science
Surface Chemistry
Organic Electronics

Background:

Large π-conjugated molecules typically remain semiconducting on metal surfaces due to a finite electronic gap.
However, metallic substrate properties can sometimes extend to the first molecular layer.

Purpose of the Study:

To elucidate the chemical mechanisms behind the transition of organic semiconductors to metallic behavior at metal interfaces.
To provide a rationale for designing stable metallic molecular monolayers.

Main Methods:

Analysis of molecular bonding and rehybridization at metal-organic interfaces.
Investigating the impact of substituents on conjugation length and electronic structure.

Main Results:

Surface bonding of specific substituents significantly increases conjugation length.
Concomitant rehybridization of the molecular backbone transforms molecules into new species with a reduced electronic gap.
Surface-induced aromatic stabilization overcomes factors maintaining the metal Fermi level within frontier orbitals.

Conclusions:

A chemical mechanism explains the emergence of metallic character in organic molecules on metal surfaces.
This understanding facilitates the design of precursors for metallic molecular monolayers.
Enables novel approaches for the chemical engineering of metal surfaces.