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

Mao-Xi Zhang; Nathaniel B. Zuckerman; Philip F. Pagoria; Bradley A. Steele; I-Feng Kuo; Gregory H. Imler; Damon Parrish

doi:10.3390/molecules26144209

Molecules (Jul 2021)

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

Mao-Xi Zhang,
Nathaniel B. Zuckerman,
Philip F. Pagoria,
Bradley A. Steele,
I-Feng Kuo,
Gregory H. Imler,
Damon Parrish

Affiliations

Mao-Xi Zhang: Lawrence Livermore National Laboratory, 7000 East Ave, Livermore, CA 94550, USA
Nathaniel B. Zuckerman: Lawrence Livermore National Laboratory, 7000 East Ave, Livermore, CA 94550, USA
Philip F. Pagoria: Lawrence Livermore National Laboratory, 7000 East Ave, Livermore, CA 94550, USA
Bradley A. Steele: Lawrence Livermore National Laboratory, 7000 East Ave, Livermore, CA 94550, USA
I-Feng Kuo: Lawrence Livermore National Laboratory, 7000 East Ave, Livermore, CA 94550, USA
Gregory H. Imler: Naval Research Laboratory, 4555 Overlook Ave, Washington, DC 20375, USA
Damon Parrish: Naval Research Laboratory, 4555 Overlook Ave, Washington, DC 20375, USA

DOI: https://doi.org/10.3390/molecules26144209
Journal volume & issue: Vol. 26, no. 14
p. 4209

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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