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Structural Organization of Dibromodiazadienes in the Crystal and Identification of Br···O Halogen Bonding Involving the Nitro Group

Nitro functionalized dibromodiazadiene dyes were prepared and fully characterized including X-ray single crystal analysis. Electron deficient dibromodiazadienes were found to be able to act as donors of halogen bonding (XB), while the nitro group acted as an acceptor of the XB. Depending on the subs...

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Autores principales: Nenajdenko, Valentine G., Shikhaliyev, Namiq G., Maharramov, Abel M., Atakishiyeva, Gulnar T., Niyazova, Aytan A., Mammadova, Naila A., Novikov, Alexander S., Buslov, Ivan V., Khrustalev, Victor N., Tskhovrebov, Alexander G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9414975/
https://www.ncbi.nlm.nih.gov/pubmed/36014350
http://dx.doi.org/10.3390/molecules27165110
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author Nenajdenko, Valentine G.
Shikhaliyev, Namiq G.
Maharramov, Abel M.
Atakishiyeva, Gulnar T.
Niyazova, Aytan A.
Mammadova, Naila A.
Novikov, Alexander S.
Buslov, Ivan V.
Khrustalev, Victor N.
Tskhovrebov, Alexander G.
author_facet Nenajdenko, Valentine G.
Shikhaliyev, Namiq G.
Maharramov, Abel M.
Atakishiyeva, Gulnar T.
Niyazova, Aytan A.
Mammadova, Naila A.
Novikov, Alexander S.
Buslov, Ivan V.
Khrustalev, Victor N.
Tskhovrebov, Alexander G.
author_sort Nenajdenko, Valentine G.
collection PubMed
description Nitro functionalized dibromodiazadiene dyes were prepared and fully characterized including X-ray single crystal analysis. Electron deficient dibromodiazadienes were found to be able to act as donors of halogen bonding (XB), while the nitro group acted as an acceptor of the XB. Depending on the substituents, the Br···O XB competed with other weak interactions, and for some of the dyes, they even outcompeted the XB involving the nitro group. However, the nitro functionalized dibromoalkenes 6a and 10a, which had only the nitro moiety as the most plausible acceptor of the XB, reliably formed 1D chains via Br⋯O XB. Experimental work was supported by the DFT calculations and topological analysis of the electron density distribution within the framework of Bader’s theory (QTAIM method).
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spelling pubmed-94149752022-08-27 Structural Organization of Dibromodiazadienes in the Crystal and Identification of Br···O Halogen Bonding Involving the Nitro Group Nenajdenko, Valentine G. Shikhaliyev, Namiq G. Maharramov, Abel M. Atakishiyeva, Gulnar T. Niyazova, Aytan A. Mammadova, Naila A. Novikov, Alexander S. Buslov, Ivan V. Khrustalev, Victor N. Tskhovrebov, Alexander G. Molecules Article Nitro functionalized dibromodiazadiene dyes were prepared and fully characterized including X-ray single crystal analysis. Electron deficient dibromodiazadienes were found to be able to act as donors of halogen bonding (XB), while the nitro group acted as an acceptor of the XB. Depending on the substituents, the Br···O XB competed with other weak interactions, and for some of the dyes, they even outcompeted the XB involving the nitro group. However, the nitro functionalized dibromoalkenes 6a and 10a, which had only the nitro moiety as the most plausible acceptor of the XB, reliably formed 1D chains via Br⋯O XB. Experimental work was supported by the DFT calculations and topological analysis of the electron density distribution within the framework of Bader’s theory (QTAIM method). MDPI 2022-08-11 /pmc/articles/PMC9414975/ /pubmed/36014350 http://dx.doi.org/10.3390/molecules27165110 Text en © 2022 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 Article
Nenajdenko, Valentine G.
Shikhaliyev, Namiq G.
Maharramov, Abel M.
Atakishiyeva, Gulnar T.
Niyazova, Aytan A.
Mammadova, Naila A.
Novikov, Alexander S.
Buslov, Ivan V.
Khrustalev, Victor N.
Tskhovrebov, Alexander G.
Structural Organization of Dibromodiazadienes in the Crystal and Identification of Br···O Halogen Bonding Involving the Nitro Group
title Structural Organization of Dibromodiazadienes in the Crystal and Identification of Br···O Halogen Bonding Involving the Nitro Group
title_full Structural Organization of Dibromodiazadienes in the Crystal and Identification of Br···O Halogen Bonding Involving the Nitro Group
title_fullStr Structural Organization of Dibromodiazadienes in the Crystal and Identification of Br···O Halogen Bonding Involving the Nitro Group
title_full_unstemmed Structural Organization of Dibromodiazadienes in the Crystal and Identification of Br···O Halogen Bonding Involving the Nitro Group
title_short Structural Organization of Dibromodiazadienes in the Crystal and Identification of Br···O Halogen Bonding Involving the Nitro Group
title_sort structural organization of dibromodiazadienes in the crystal and identification of br···o halogen bonding involving the nitro group
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9414975/
https://www.ncbi.nlm.nih.gov/pubmed/36014350
http://dx.doi.org/10.3390/molecules27165110
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