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

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

doi:10.3390/molecules26144209

DOE OSTI · 1807762

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

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

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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 AcONO 2 and NO 2 BF 4 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.

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY BN aromatics chemistry nitration nitro-BN-naphthalene nitro-azaborine

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Zhang, Mao-Xi, Zuckerman, Nathaniel B., Pagoria, Philip F., Steele, Bradley A., Kuo, I-Feng, Imler, Gregory H., Parrish, Damon. 2021-07-11. Mono- and Dinitro-BN-Naphthalenes: Formation and Characterization. https://doi.org/10.3390/molecules26144209

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