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Hybridization of Atomic Orbitals I

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Related Experiment Video

Updated: Jul 13, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

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Published on: February 15, 2016

T-Shaped Stibenium(III) Cation: Hydrostibination Without Sb─H Bond.

Ekta Nag¹, Lars Ole Busse¹, Andreas Albers¹

¹Anorganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Heidelberg, Germany.

Angewandte Chemie (International Ed. in English)

|July 11, 2026

Summary

Researchers developed a new method for hydrostibination, avoiding unstable antimony-hydride reagents. A novel stibenium(III) ion enables efficient anti-Markovnikov addition to alkenes, paving the way for heavy p-block element chemistry.

Keywords:

antimony anti‐Markovnikov element–ligand cooperativity hydroelementation hydrostibination

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Published on: February 9, 2017

Area of Science:

Organometallic Chemistry
Main Group Chemistry
Synthetic Methodology

Background:

Hydrostibination of alkenes is an underdeveloped transformation due to the instability of antimony-hydride (Sb─H) reagents.
Existing methods often rely on labile E─H bonds, limiting their applicability in synthetic chemistry.

Purpose of the Study:

To develop a novel hydrostibination strategy that circumvents the need for traditional Sb─H reagents.
To explore the reactivity of a structurally constrained stibenium(III) ion in alkene functionalization.
To establish a viable method for hydroelementation with heavy p-block elements.

Main Methods:

Synthesis and characterization of a T-shaped amidophenolato-pyridyl supported stibenium(III) ion.
Investigation of the anti-Markovnikov hydrostibination of diverse alkenes using the stibenium(III) ion.
Spectroscopic (NMR, X-ray crystallography) and computational (DFT) analyses to elucidate the electronic structure and reaction mechanism.
Mechanistic studies to probe element-ligand cooperativity (ELC).

Main Results:

The stibenium(III) ion successfully mediated anti-Markovnikov hydrostibination of a broad range of alkenes in excellent yields.
Spectroscopic and computational data revealed a polarizable, redox-confused Sb-π system, with reactivity characteristic of a Lewis-acidic Sb(III) center.
Mechanistic studies indicated element-ligand cooperativity, where the hydride equivalent originates from the ligand scaffold.
The resulting stiba-alkanes were quantitatively converted into haloalkanes.

Conclusions:

A robust and efficient hydrostibination method has been established, overcoming the limitations of labile Sb─H reagents.
The study demonstrates the utility of a novel stibenium(III) ion for hydroelementation with heavy p-block elements.
This work opens new avenues for synthetic applications involving heavy main group elements.