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

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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.

In: Molecules, Vol. 27, No. 16, 5110, 11.08.2022.

Research output: Contribution to journal › Article › peer-review

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. / Structural Organization of Dibromodiazadienes in the Crystal and Identification of Br···O Halogen Bonding Involving the Nitro Group. In: Molecules. 2022 ; Vol. 27, No. 16.

BibTeX

@article{ef8e818f20b04f51853735ec7d7f3603,

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

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{\textquoteright}s theory (QTAIM method).",

keywords = "azo dyes, DFT, halogen bonding, non-covalent interactions, QTAIM",

author = "Nenajdenko, {Valentine G.} and Shikhaliyev, {Namiq G.} and Maharramov, {Abel M.} and Atakishiyeva, {Gulnar T.} and Niyazova, {Aytan A.} and Mammadova, {Naila A.} and Novikov, {Alexander S.} and Buslov, {Ivan V.} and Khrustalev, {Victor N.} and Tskhovrebov, {Alexander G.}",

note = "Nenajdenko, V.G.; Shikhaliyev, N.G.; Maharramov, A.M.; Atakishiyeva, G.T.; Niyazova, A.A.; Mammadova, N.A.; Novikov, A.S.; Buslov, I.V.; Khrustalev, V.N.; Tskhovrebov, A.G. Structural Organization of Dibromodiazadienes in the Crystal and Identification of Br···O Halogen Bonding Involving the Nitro Group. Molecules 2022, 27, 5110. https://doi.org/10.3390/molecules27165110",

year = "2022",

month = aug,

day = "11",

doi = "10.3390/molecules27165110",

language = "English",

volume = "27",

journal = "Molecules",

issn = "1420-3049",

publisher = "MDPI AG",

number = "16",

}

RIS

TY - JOUR

T1 - Structural Organization of Dibromodiazadienes in the Crystal and Identification of Br···O Halogen Bonding Involving the Nitro Group

AU - Nenajdenko, Valentine G.

AU - Shikhaliyev, Namiq G.

AU - Maharramov, Abel M.

AU - Atakishiyeva, Gulnar T.

AU - Niyazova, Aytan A.

AU - Mammadova, Naila A.

AU - Novikov, Alexander S.

AU - Buslov, Ivan V.

AU - Khrustalev, Victor N.

AU - Tskhovrebov, Alexander G.

N1 - Nenajdenko, V.G.; Shikhaliyev, N.G.; Maharramov, A.M.; Atakishiyeva, G.T.; Niyazova, A.A.; Mammadova, N.A.; Novikov, A.S.; Buslov, I.V.; Khrustalev, V.N.; Tskhovrebov, A.G. Structural Organization of Dibromodiazadienes in the Crystal and Identification of Br···O Halogen Bonding Involving the Nitro Group. Molecules 2022, 27, 5110. https://doi.org/10.3390/molecules27165110

PY - 2022/8/11

Y1 - 2022/8/11

N2 - 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).

AB - 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).

KW - azo dyes

KW - DFT

KW - halogen bonding

KW - non-covalent interactions

KW - QTAIM

UR - http://www.scopus.com/inward/record.url?scp=85136700286&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/fe0dcae8-b427-3cd9-823a-3cbde39f70f3/

U2 - 10.3390/molecules27165110

DO - 10.3390/molecules27165110

M3 - Article

C2 - 36014350

AN - SCOPUS:85136700286

VL - 27

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 16

M1 - 5110

ER -

ID: 98879608