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

Valentine G Nenajdenko; Namiq G Shikhaliyev; Abel M Maharramov; Gulnar T Atakishiyeva; Aytan A Niyazova; Naila A Mammadova; Alexander S Novikov; Ivan V Buslov; Victor N Khrustalev; Alexander G Tskhovrebov

doi:10.3390/molecules27165110

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

Molecules. 2022 Aug 11;27(16):5110. doi: 10.3390/molecules27165110.

Affiliations

¹ Department of Chemistry, M. V. Lomonosov Moscow State University, 1, Leninskie Gory, Moscow 119991, Russia.
² Department of Organic Chemistry, Baku State University, Z. Xalilov 23, Baku AZ1000, Azerbaijan.
³ Department of Engineering and Applied Sciences, Azerbaijan State University of Economics, M.Mukhtarov 194, Baku AZ1001, Azerbaijan.
⁴ Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7/9, Saint Petersburg 199034, Russia.
⁵ Research Institute of Chemistry, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya Street, Moscow 117198, Russia.
⁶ N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Av., Moscow 119334, Russia.

Abstract

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).

Keywords: DFT; QTAIM; azo dyes; halogen bonding; non-covalent interactions.

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

Authors

Affiliations

Abstract

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