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Updated: Jun 1, 2026
09:04
A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
4-Guanidinobenzene-sulfonic acid.
Summary
The zwitterionic compound 4-{[amino(inimio)methyl]amino}benzenesulfonate exhibits a specific dihedral angle between its guanidine group and benzene ring. Crystal packing is primarily stabilized by intermolecular hydrogen bonds, highlighting its structural characteristics.
Area of Science:
- Crystallography
- Chemical Physics
- Organic Chemistry
Background:
- Understanding the structural and bonding characteristics of zwitterionic compounds is crucial in materials science and drug design.
- Guanidine derivatives are known for their diverse chemical properties and biological activities.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the zwitterionic compound 4-{[amino(inimio)methyl]amino}benzenesulfonate.
- To quantify the spatial arrangement between the guanidine moiety and the benzene ring system.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
- Analysis of bond lengths, bond angles, and intermolecular contacts, including hydrogen bonding, was performed.
Main Results:
- The crystal structure revealed a zwitterionic form of 4-{[amino(inimio)methyl]amino}benzenesulfonate.
- A dihedral angle of 44.87(7)° was measured between the guanidine group and the benzene ring.
- Intermolecular N-H⋯O hydrogen bonds were identified as the primary stabilizing force in the crystal lattice, involving all potential hydrogen bond donors.
Conclusions:
- The study provides detailed structural insights into a specific zwitterionic benzenesulfonate derivative.
- The observed dihedral angle suggests a non-planar conformation between the key functional groups.
- The prevalence of intermolecular hydrogen bonding dictates the crystal packing and stability of the compound.
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