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 AcONO(2) and NO(2)BF(4) in acetonitrile. The nitrated products were isolat...

Descripción completa

Detalles Bibliográficos
Autores principales: Zhang, Mao-Xi, Zuckerman, Nathaniel B., Pagoria, Philip F., Steele, Bradley A., Kuo, I-Feng, Imler, Gregory H., Parrish, Damon
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8303104/
https://www.ncbi.nlm.nih.gov/pubmed/34299484
http://dx.doi.org/10.3390/molecules26144209
_version_ 1783727006826889216
author Zhang, Mao-Xi
Zuckerman, Nathaniel B.
Pagoria, Philip F.
Steele, Bradley A.
Kuo, I-Feng
Imler, Gregory H.
Parrish, Damon
author_facet Zhang, Mao-Xi
Zuckerman, Nathaniel B.
Pagoria, Philip F.
Steele, Bradley A.
Kuo, I-Feng
Imler, Gregory H.
Parrish, Damon
author_sort Zhang, Mao-Xi
collection PubMed
description 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.
format Online
Article
Text
id pubmed-8303104
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-83031042021-07-25 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 Molecules Communication 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. MDPI 2021-07-11 /pmc/articles/PMC8303104/ /pubmed/34299484 http://dx.doi.org/10.3390/molecules26144209 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Zhang, Mao-Xi
Zuckerman, Nathaniel B.
Pagoria, Philip F.
Steele, Bradley A.
Kuo, I-Feng
Imler, Gregory H.
Parrish, Damon
Mono- and Dinitro-BN-Naphthalenes: Formation and Characterization
title Mono- and Dinitro-BN-Naphthalenes: Formation and Characterization
title_full Mono- and Dinitro-BN-Naphthalenes: Formation and Characterization
title_fullStr Mono- and Dinitro-BN-Naphthalenes: Formation and Characterization
title_full_unstemmed Mono- and Dinitro-BN-Naphthalenes: Formation and Characterization
title_short Mono- and Dinitro-BN-Naphthalenes: Formation and Characterization
title_sort mono- and dinitro-bn-naphthalenes: formation and characterization
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8303104/
https://www.ncbi.nlm.nih.gov/pubmed/34299484
http://dx.doi.org/10.3390/molecules26144209
work_keys_str_mv AT zhangmaoxi monoanddinitrobnnaphthalenesformationandcharacterization
AT zuckermannathanielb monoanddinitrobnnaphthalenesformationandcharacterization
AT pagoriaphilipf monoanddinitrobnnaphthalenesformationandcharacterization
AT steelebradleya monoanddinitrobnnaphthalenesformationandcharacterization
AT kuoifeng monoanddinitrobnnaphthalenesformationandcharacterization
AT imlergregoryh monoanddinitrobnnaphthalenesformationandcharacterization
AT parrishdamon monoanddinitrobnnaphthalenesformationandcharacterization

Ejemplares similares