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

Mono- and dinitro-BN-naphthalenes, i.e., 1-nitro-, 3-nitro-, 1,6-dinitro-, 3,6-dinitro-, and 1,8-dinitro-BNN, were generated in the nitration of 9,10-BN-naphthalene (BNN), a boron–nitrogen (BN) bond-embedded naphthalene, with AcONO2 and NO2BF4 in acetonitrile. The nitrated products were isolated and...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2021-07, Vol.26 (14), p.4209
Main Authors: Zhang, Mao-Xi, Zuckerman, Nathaniel B., Pagoria, Philip F., Steele, Bradley A., Kuo, I-Feng, Imler, Gregory H., Parrish, Damon
Format: Article
Language:English
Subjects:
Acetonitrile
Aromaticity
BN aromatics
Boron
Carbon
chemistry
Communication
Crystallography
Electron density
INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Naphthalene
nitration
nitro-azaborine
nitro-BN-naphthalene
Nitrogen
Reagents
Spectrum analysis
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Summary:Mono- and dinitro-BN-naphthalenes, i.e., 1-nitro-, 3-nitro-, 1,6-dinitro-, 3,6-dinitro-, and 1,8-dinitro-BNN, were generated in the nitration of 9,10-BN-naphthalene (BNN), a boron–nitrogen (BN) bond-embedded naphthalene, with AcONO2 and NO2BF4 in acetonitrile. The nitrated products were isolated and characterized by NMR, GC-MS, IR, and X-ray single crystallography. The effects of the nitration on the electron density and aromaticity of BNN were evaluated by B-11 NMR analysis and HOMA calculations.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules26144209