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Regioselective Formation of Enolates

Regioselective Formation of Enolates

As depicted in the figure below, the unsymmetrical ketones can form two possible enolates: less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are more stable. But the energy required to form kinetic enolates is less.

π Molecular Orbitals of 1,3-Butadiene

π Molecular Orbitals of 1,3-Butadiene

Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...

Enolate Mechanism Conventions

Enolate Mechanism Conventions

When a carbonyl compound is treated with a strong base, the α position gets deprotonated to give a resonance-stabilized intermediate called an enolate. Enolates are ambident nucleophiles because they possess two nucleophilic sites that can attack an electrophile owing to the delocalization of the negative charge between the α carbon and oxygen atoms. When the oxygen atom attacks an electrophile, it is called O-attack, whereas electrophilic attack via the α carbon is known as C-attack.
C-attack...

C–C Bond Formation: Aldol Condensation Overview

C–C Bond Formation: Aldol Condensation Overview

Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. The aldol condensation reaction presented in Figure 1 constitutes an aldol addition reaction followed by the dehydration process.

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...

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Synthesis, Assembly, and Characterization of Monolayer Protected Gold Nanoparticle Films for Protein Monolayer Electrochemistry

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Formation and Evolution of Metallocene Single-Molecule Circuits with Direct Gold-π Links.

Brent Lawson¹, Percy Zahl², Mark S Hybertsen²

¹Department of Physics, Boston University, Boston, Massachusetts 02215, United States.

Journal of the American Chemical Society

|March 30, 2022

Summary

Group 8 metallocenes form direct gold-π bonds in single-molecule circuits, enabling stable molecular junctions. Conductance is independent of electrode sharpness, revealing distinct binding mechanisms for molecular electronics.

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Area of Science:

Molecular electronics
Nanotechnology
Physical chemistry

Background:

Single-molecule circuits are crucial for advancing molecular electronics.
Understanding electrode-molecule interactions is key to controlling junction properties.
Metallocenes offer unique electronic properties for molecular wire applications.

Purpose of the Study:

Investigate direct gold-π binding in metallocene-based single-molecule circuits.
Characterize the effect of this binding on molecular conductance and junction evolution.
Elucidate the atomic-scale mechanisms of metallocene-gold electrode interactions.

Main Methods:

Scanning tunneling microscope-based break junction (STMBJ) measurements at cryogenic and room temperatures.
Analysis of molecular plateau persistence during junction extension and compression.
Density functional theory (DFT)-based calculations for modeling electrode-molecule interfaces.

Main Results:

Direct gold-π binding formed stable single-molecule circuits with group 8 metallocenes without linkers.
Junction persistence correlated with electrode tip geometry (sharp vs. blunt).
Two distinct binding modes identified: donor-acceptor bonds on sharp tips and van der Waals interactions on blunt tips.
Molecular conductance was largely independent of electrode atomic structure.
Non-specific interactions led to extended conductance plateaus.

Conclusions:

Direct gold-π interactions enable robust metallocene single-molecule junctions.
Electrode geometry influences binding modes but not significantly conductance.
Metallocene-based circuits offer a distinct mechanism for stable molecular wires compared to traditional rod-shaped molecules.