Related Experiment Video
Updated: Jun 14, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
COMPAS-4: A Data Set of (BN)1 Substituted Cata-Condensed Polybenzenoid Hydrocarbons─Data Analysis and Feature
Sabyasachi Chakraborty1, Itay Almog1, Renana Gershoni-Poranne1
1The Schulich Faculty of Chemistry and the Resnick Sustainability Center for Catalysis, Technion - Israel Institute of Technology, Haifa 32000, Israel.
Abstract:
Incorporation of a boron-nitrogen (BN) pair into polycyclic aromatic hydrocarbons is a common approach for modulating their electronic properties. However, a conceptual and quantitative framework rationalizing the observed effects has not been developed, and general structure-property relationships remain elusive. In this work, we perform a data-driven investigation that leads to concrete principles for rational design of (BN)1-PBHs with targeted properties. We construct a new chemical database, COMPAS-4, which contains the geometries and properties of all possible (BN)1-PBH isomers up to 6 rings, calculated at both the GFN1-xTB and density functional theory (DFT) (CAM-B3LYP/def2-SVP) levels of theory. We investigate the influence of BN-substitution on various molecular properties, including their molecular orbital energies and aromaticity, and define specific structural features that determine these properties. Notably, all of these features are chemically intuitive and simple to extract from the structure of the molecule, without any prior computation. We find that the most influential feature is the number of rings whose cyclic delocalization is disturbed as a result of the substitution.
More Related Videos
Related Concept Videos
Nomenclature of Aromatic Compounds with a Single Substituent
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation
Structure of Benzene: Kekulé Model
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
Nucleophilic Aromatic Substitution: Elimination–Addition
Nomenclature of Aromatic Compounds with Multiple Substituents
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
Aromatic Compounds: Overview
In 1825, Faraday...

