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

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.

SUBMITTER: Zhang MX

PROVIDER: S-EPMC8303104 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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

Zhang Mao-Xi MX Zuckerman Nathaniel B NB Pagoria Philip F PF Steele Bradley A BA Kuo I-Feng IF Imler Gregory H GH Parrish Damon D

Molecules (Basel, Switzerland) 20210711 14

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 ...[more]

PMID: 34299484

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