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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Veröffentlicht in:	Molecules (Basel, Switzerland) Switzerland), 2021-07, Vol.26 (14), p.4209
Hauptverfasser:	Zhang, Mao-Xi, Zuckerman, Nathaniel B., Pagoria, Philip F., Steele, Bradley A., Kuo, I-Feng, Imler, Gregory H., Parrish, Damon
Format:	Artikel
Sprache:	eng
Schlagworte:	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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Beschreibung
Zusammenfassung:	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