Polybromides of pyridinium and quinolinium-type cations: Cation-induced structural diversity and theoretical analysis of Br⋯Br interactions

Igor D. Gorokh, Sergey A. Adonin, Alexander S. Novikov, Maxim N. Sokolov, Denis G. Samsonenko, Vladimir P. Fedin

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Four novel polybromide salts containing pyridinium-type and quinolinium-type cations – {(2-Br-5-MePy)2H}Br3 (1), (1,3,5-MePy){(Br3) (Br2)} (2), (1-Et-2,6-MePy){(Br3) (Br2)0.5} (3) and (N-MeIsoquin){(Br3) (Br2)0.5} (4) were isolated from HBr/Br2 solutions. Hirshfeld surface analysis for the organic parts of X-ray structures of 1–4 and a set of related compounds reported earlier reveals that in all cases crystal packing is determined primarily by intermolecular contacts BrH, HH, С–H, BrBr, and BrC. DFT calculations allowed estimation of Br⋯Br halogen bonding energies (0.9–7.5 kcal/mol).
LanguageRussian
Pages725-731
Number of pages7
JournalJournal of Molecular Structure
Volume1179
DOIs
StatePublished - 2019

Keywords

    Cite this

    Gorokh, Igor D. ; Adonin, Sergey A. ; Novikov, Alexander S. ; Sokolov, Maxim N. ; Samsonenko, Denis G. ; Fedin, Vladimir P. / Polybromides of pyridinium and quinolinium-type cations: Cation-induced structural diversity and theoretical analysis of Br⋯Br interactions. In: Journal of Molecular Structure. 2019 ; Vol. 1179. pp. 725-731.
    @article{8ee09c7680154b8595e03995398f8be8,
    title = "Polybromides of pyridinium and quinolinium-type cations: Cation-induced structural diversity and theoretical analysis of Br⋯Br interactions",
    abstract = "Four novel polybromide salts containing pyridinium-type and quinolinium-type cations – {(2-Br-5-MePy)2H}Br3 (1), (1,3,5-MePy){(Br3) (Br2)} (2), (1-Et-2,6-MePy){(Br3) (Br2)0.5} (3) and (N-MeIsoquin){(Br3) (Br2)0.5} (4) were isolated from HBr/Br2 solutions. Hirshfeld surface analysis for the organic parts of X-ray structures of 1–4 and a set of related compounds reported earlier reveals that in all cases crystal packing is determined primarily by intermolecular contacts BrH, HH, С–H, BrBr, and BrC. DFT calculations allowed estimation of Br⋯Br halogen bonding energies (0.9–7.5 kcal/mol).",
    keywords = "Polybromides, QTAIM, Halogen bonding, X-ray diffractometry, Supramolecular contacts",
    author = "Gorokh, {Igor D.} and Adonin, {Sergey A.} and Novikov, {Alexander S.} and Sokolov, {Maxim N.} and Samsonenko, {Denis G.} and Fedin, {Vladimir P.}",
    year = "2019",
    doi = "10.1016/j.molstruc.2018.11.070",
    language = "русский",
    volume = "1179",
    pages = "725--731",
    journal = "Journal of Molecular Structure",
    issn = "0022-2860",
    publisher = "Elsevier",

    }

    Polybromides of pyridinium and quinolinium-type cations: Cation-induced structural diversity and theoretical analysis of Br⋯Br interactions. / Gorokh, Igor D.; Adonin, Sergey A.; Novikov, Alexander S.; Sokolov, Maxim N.; Samsonenko, Denis G.; Fedin, Vladimir P.

    In: Journal of Molecular Structure, Vol. 1179, 2019, p. 725-731.

    Research output: Contribution to journalArticleResearchpeer-review

    TY - JOUR

    T1 - Polybromides of pyridinium and quinolinium-type cations: Cation-induced structural diversity and theoretical analysis of Br⋯Br interactions

    AU - Gorokh, Igor D.

    AU - Adonin, Sergey A.

    AU - Novikov, Alexander S.

    AU - Sokolov, Maxim N.

    AU - Samsonenko, Denis G.

    AU - Fedin, Vladimir P.

    PY - 2019

    Y1 - 2019

    N2 - Four novel polybromide salts containing pyridinium-type and quinolinium-type cations – {(2-Br-5-MePy)2H}Br3 (1), (1,3,5-MePy){(Br3) (Br2)} (2), (1-Et-2,6-MePy){(Br3) (Br2)0.5} (3) and (N-MeIsoquin){(Br3) (Br2)0.5} (4) were isolated from HBr/Br2 solutions. Hirshfeld surface analysis for the organic parts of X-ray structures of 1–4 and a set of related compounds reported earlier reveals that in all cases crystal packing is determined primarily by intermolecular contacts BrH, HH, С–H, BrBr, and BrC. DFT calculations allowed estimation of Br⋯Br halogen bonding energies (0.9–7.5 kcal/mol).

    AB - Four novel polybromide salts containing pyridinium-type and quinolinium-type cations – {(2-Br-5-MePy)2H}Br3 (1), (1,3,5-MePy){(Br3) (Br2)} (2), (1-Et-2,6-MePy){(Br3) (Br2)0.5} (3) and (N-MeIsoquin){(Br3) (Br2)0.5} (4) were isolated from HBr/Br2 solutions. Hirshfeld surface analysis for the organic parts of X-ray structures of 1–4 and a set of related compounds reported earlier reveals that in all cases crystal packing is determined primarily by intermolecular contacts BrH, HH, С–H, BrBr, and BrC. DFT calculations allowed estimation of Br⋯Br halogen bonding energies (0.9–7.5 kcal/mol).

    KW - Polybromides

    KW - QTAIM

    KW - Halogen bonding

    KW - X-ray diffractometry

    KW - Supramolecular contacts

    U2 - 10.1016/j.molstruc.2018.11.070

    DO - 10.1016/j.molstruc.2018.11.070

    M3 - статья

    VL - 1179

    SP - 725

    EP - 731

    JO - Journal of Molecular Structure

    T2 - Journal of Molecular Structure

    JF - Journal of Molecular Structure

    SN - 0022-2860

    ER -