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Related Experiment Video

Updated: May 27, 2026

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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2-(Tritylsulfan-yl)ethyl 2-iodo-benzoate.

Xin Zhu, Ping Lu, Seik Weng Ng

Acta Crystallographica. Section E, Structure Reports Online

|November 8, 2011

Summary

Structural analysis of C(28)H(23)IO(2)S reveals a flattened methine carbon in the triphenyl-methyl group. The connecting chain adopts an extended, planar zigzag conformation, offering insights into molecular geometry.

Area of Science:

Organic Chemistry
Crystallography
Molecular Structure

Background:

Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
The triphenyl-methyl group is a common bulky substituent in organic chemistry, and its conformational flexibility can influence molecular packing and interactions.
The specific compound C(28)H(23)IO(2)S presents an interesting case for structural investigation due to its unique combination of functional groups.

Purpose of the Study:

To elucidate the precise molecular geometry and conformational preferences of the title compound, C(28)H(23)IO(2)S.
To analyze the spatial arrangement of the triphenyl-methyl group and the connecting chain within the crystal structure.
To provide detailed crystallographic data for a novel organic compound.

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Published on: June 28, 2011

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Published on: June 28, 2011

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of C(28)H(23)IO(2)S.
Analysis of bond lengths, bond angles, and torsion angles was performed to describe the molecular conformation.
Root-mean-square deviation calculations were used to assess the planarity of specific molecular fragments.

Main Results:

The methine carbon atom within the triphenyl-methyl group exhibits a slightly flattened geometry, with ΣC(phen-yl)-C-C(phen-yl) angles measuring 335.6(5)°.
The -C-O-C-C-S- chain linking the triphenyl-methyl moiety to the aromatic ring adopts an extended, planar zigzag conformation.
The five atoms of the connecting chain lie on an approximate plane, with a root-mean-square deviation of 0.120 Å.

Conclusions:

The crystal structure of C(28)H(23)IO(2)S reveals specific conformational constraints around the triphenyl-methyl group and its connecting chain.
The observed planarity of the connecting chain suggests potential electronic delocalization or specific intermolecular interactions.
These findings contribute to the understanding of structure-property relationships in complex organic molecules.