Mono- and Dinitro-BN-Naphthalenes: Formation and Characterization.

Area of Science:

• Organic Chemistry
• Materials Science
• Aromatic Chemistry

Background:

• Boron-nitrogen (BN) naphthalene (BNN) is an aromatic compound with unique electronic properties.
• Nitration is a key reaction for functionalizing aromatic systems.
• Understanding the impact of nitration on BNN's electronic structure is crucial for its applications.

Purpose of the Study:

• To synthesize and characterize mono- and dinitro derivatives of 9,10-BN-naphthalene (BNN).
• To investigate the effects of nitration on the electron density and aromaticity of BNN.
• To explore the reactivity and properties of BN-embedded aromatic systems.

Main Methods:

• Nitration of 9,10-BN-naphthalene using AcONO2 and NO2BF4 in acetonitrile.
• Isolation and characterization of nitrated products using NMR, GC-MS, IR, and X-ray crystallography.
• Evaluation of electronic properties via B-11 NMR and HOMA calculations.

Main Results:

• Successfully synthesized and identified five nitrated BNN compounds: 1-nitro-, 3-nitro-, 1,6-dinitro-, 3,6-dinitro-, and 1,8-dinitro-BNN.
• Characterization confirmed the structures of the nitrated products.
• Analysis revealed significant changes in electron density and aromaticity upon nitration.

Conclusions:

• Nitration provides a viable route to functionalize BNN.
• The study elucidates the impact of nitro groups on the electronic landscape and aromatic character of BNN.
• Findings contribute to the understanding of BN-containing aromatic compounds and their potential modification.