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Related Concept Videos

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.

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From an unusual organotin(IV) coordination compound to the first ionic organic-inorganic mixed-valent tin(IV)-tin(II) compound.

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Related Experiment Video

Updated: May 10, 2026

Synthesis of a Deuterated Standard for the Quantification of 2-Arachidonoylglycerol in Caenorhabditis elegans
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Synthesis of a Deuterated Standard for the Quantification of 2-Arachidonoylglycerol in Caenorhabditis elegans

Published on: September 21, 2019

Diacetatodi-tert-butyltin(IV).

Martin Reichelt1, Hans Reuter

  • 1Institut für Chemie neuer Materialien, Strukturchemie, Universität Osnabrück, Barbarastr. 7, D-49069 Osnabrück, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|June 1, 2013
PubMed
Summary

Large tert-butyl groups significantly alter diorganotin diacetate structures, lengthening tin-carbon bonds and enhancing acetate interactions. This leads to a unique chain-like molecular arrangement through C-H⋯O bonds.

Area of Science:

  • Organometallic Chemistry
  • Crystallography
  • Materials Science

Background:

  • Diorganotin diacetates are a class of organometallic compounds with diverse applications.
  • Understanding their molecular structure is crucial for predicting and controlling their properties.
  • Previous studies characterized diorganotin diacetates with various organic groups.

Purpose of the Study:

  • To synthesize and characterize a novel diorganotin diacetate with bulky tert-butyl groups.
  • To investigate the influence of these large organic groups on the molecular structure of diorganotin diacetates.
  • To compare the structural features with previously studied diorganotin diacetates.

Main Methods:

  • Synthesis of the title compound, di-tert-butyltin diacetate [Sn(C4H9)2(CH3COO)2].

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

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Last Updated: May 10, 2026

Synthesis of a Deuterated Standard for the Quantification of 2-Arachidonoylglycerol in Caenorhabditis elegans
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

  • X-ray crystallography to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and intermolecular interactions.

    • Main Results:

    • The synthesized compound [Sn(C4H9)2(CH3COO)2] adopts a molecular structure similar to other diorganotin(IV) diacetates, featuring unsymmetrical bidentate acetate coordination.
    • Significant structural differences were observed due to the tert-butyl groups: elongated tin-carbon bonds and strengthened interactions between acetate groups and the tin atom.
    • Intermolecular interactions are primarily C-H⋯O hydrogen bonds, resulting in a chain-like arrangement of molecules.

    Conclusions:

    • Bulky tert-butyl groups exert a notable steric influence on the molecular structure of diorganotin diacetates.
    • The observed structural modifications, including longer Sn-C bonds and enhanced Sn-O interactions, are key consequences of steric hindrance.
    • The study provides valuable insights into structure-property relationships in organotin compounds, relevant for materials science and coordination chemistry.