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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Aromaticity in cyanuric acid.
Liliana Pérez-Manríquez1, Armando Cabrera, Luis Enrique Sansores
1Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Coyoacán, México City, Mexico.
Journal of Molecular Modeling
|September 8, 2010
Summary
Cyanuric acid and its derivatives exhibit aromatic character. The simplest form, cyanuric acid (hexahydrotriazine), shows the highest aromatic stabilization energy (ASE) among the studied compounds.
Area of Science:
- Organic Chemistry
- Computational Chemistry
Background:
- Aromaticity is a key concept in organic chemistry, influencing molecular stability and reactivity.
- Cyanuric acid (hexahydrotriazine) and its derivatives are nitrogen-containing heterocyclic compounds with potential aromatic properties.
Purpose of the Study:
- To investigate and quantify the aromatic nature of cyanuric acid and its derivatives.
- To analyze the electronic behavior and structural characteristics related to aromaticity.
Main Methods:
- Calculation of aromatic stabilization energy (ASE) for various cyanuric acid derivatives.
- Analysis of molecular orbitals to understand electronic distribution.
- Evaluation of inductive effects on aromatic character.
Main Results:
- Cyanuric acid (C(3)N(3)O(3)H(3)) exhibits the strongest aromaticity within the analyzed set.
- Several derivatives of cyanuric acid also display significant aromatic character.
- Molecular orbital analysis and inductive effects provide insights into the observed aromaticity.
Conclusions:
- The aromaticity of cyanuric acid and its derivatives is confirmed and quantifiable.
- Structural and electronic factors, including inductive effects, modulate the degree of aromaticity.
- This study contributes to understanding the electronic properties of nitrogen-containing heterocycles.
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