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

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Nenajdenko V. G., Shikhaliyev N. G., Maharramov A. M., Atakishiyeva G. T., Niyazova A., Mammadova N. A., ...More

MOLECULES, vol.27, no.16, 2022 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 27 Issue: 16
  • Publication Date: 2022
  • Doi Number: 10.3390/molecules27165110
  • Journal Name: MOLECULES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, Communication Abstracts, EMBASE, Food Science & Technology Abstracts, MEDLINE, Metadex, Veterinary Science Database, Directory of Open Access Journals, Civil Engineering Abstracts
  • Azerbaijan State University of Economics (UNEC) Affiliated: Yes

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 center dot center dot center dot 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 BrMIDLINE HORIZONTAL ELLIPSISO 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).