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π Molecular Orbitals of the Allyl Cation and Anion

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An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with an...

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
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π Molecular Orbitals of the Allyl Radical

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Allyl radicals are three-carbon conjugated systems. They are readily formed as intermediates in halogenation reactions of alkenes involving the addition of halogen to the allylic carbon instead of the double bond. As seen in allyl cations and anions, each of the three sp2-hybridized carbon atoms in allyl radicals has an unhybridized p orbital. These orbitals combine to give three π molecular orbitals.
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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

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Published on: July 30, 2017

Biomimetic all-metal Pd₁₁ helicene.

Yan Sun^1,2, Shuguang Wang¹, Jiachun Li¹

¹Key Laboratory of Advanced Biomaterials and Nanomedicine in Universities of Shandong, Linyi University, Linyi 276000, China.

Science Advances

|July 15, 2026

Summary

Researchers synthesized a novel antimony (Sb)-centered palladium (Pd) metallic helicene cluster. This all-metal structure shows exceptional electrocatalytic activity for oxygen reduction, advancing the field of metallic helicenes.

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

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Published on: February 7, 2017

Area of Science:

Inorganic Chemistry
Supramolecular Chemistry
Materials Science

Background:

Helicenes are chiral polycyclic aromatic compounds with unique photoelectrical properties.
All-metal helicenes are challenging to synthesize due to difficulties in controlling metal coordination, helical propagation, and stability.
Existing research has focused on carbon-based helicenes and heterohelicenes, leaving all-metal helicenes underexplored.

Purpose of the Study:

To report the rational synthesis of a novel all-metal helicene.
To investigate the structural, electronic, and catalytic properties of the synthesized metallic helicene.
To explore the potential applications of all-metal helicenes in catalysis.

Main Methods:

Synthesis of a stibine/thiolate-protected palladium (Pd) metallic helicene cluster, Pd11(PhSb)2(AdmS)10.
Structural characterization using X-ray crystallography and other spectroscopic techniques.
Electrocatalytic evaluation for the oxygen reduction reaction (ORR) using operando infrared spectroscopy and density functional theory (DFT) calculations.

Main Results:

An unprecedented scallop-like all-metal helicene architecture, an antimony (Sb)-centered [3]Pd-helicene cluster, was successfully synthesized.
The cluster features a Pd11 framework with unique 7-center-2-electron (7c-2e) sigma bonds, contributing to its stability.
The metallic helicene demonstrated exceptional electrocatalytic activity for the two-electron oxygen reduction reaction (ORR).
A chiral homolog was obtained through structural unfolding, indicating dynamic structural behavior.

Conclusions:

This work presents a significant advancement in the synthesis of all-metal helicenes.
The Sb-centered [3]Pd-helicene cluster showcases promising electrocatalytic properties for ORR.
The findings open new avenues for the rational design and functional application of all-metal helicenes in catalysis and materials science.