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

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

Molecules. 2021 Jul 11;26(14):4209. doi: 10.3390/molecules26144209.

Authors

Mao-Xi Zhang¹, Nathaniel B Zuckerman¹, Philip F Pagoria¹, Bradley A Steele¹, I-Feng Kuo¹, Gregory H Imler², Damon Parrish²

Affiliations

¹ Lawrence Livermore National Laboratory, 7000 East Ave, Livermore, CA 94550, USA.
² Naval Research Laboratory, 4555 Overlook Ave, Washington, DC 20375, USA.

Abstract

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.

Keywords: BN aromatics; nitration; nitro-BN-naphthalene; nitro-azaborine.

Abstract

Grants and funding