Halogen bonding in Wagner-Meerwein rearrangement products

Crystal structure and Hirshfeld surface analysis of (E)-3-[(2,3-dichlorobenzylidene)amino]-5-phenylthiazolidin-2-iminium bromide

“…Schiff bases of heterocyclic amines and their complexes have attracted attention over the past decades not only due to the relatively easy synthesis, but also in view of their potential biological, pharmacological and analytical applications (Akbari et al, 2017;Gurbanov et al, 2018a,b;Hazra et al, 2018;Kvyatkovskaya et al, 2017;Mahmoudi et al, 2016Mahmoudi et al, , 2017aMahmoudi et al, ,b, 2018aMitoraj et al, 2018;Shetnev et al, 2017). Non-covalent interactions play an important role in the stabilization of coordination or supramolecular compounds derived from Schiff bases (Mahmudov et al, 2016(Mahmudov et al, , 2017aZubkov et al, 2018). Herein we report strong charge-assisted hydrogen bonds and halogen bonding in the structure of (E)-3-[(2,3-dichlorobenzylidene)amino]-5-phenylthiazolidin-2iminium bromide.…”

Crystal structure and Hirshfeld surface analysis of 4,5-dibromo-6-methyl-2-phenyl-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1H-isoindol-1-one

“…Analysis of the literature data does not allow one to reliably predict the direction of the halogenation of oxabicycloheptenes. It can on the one hand be the halogen-initiated Wagner-Meerwein cationic rearrangement (Jung et al, 1985;Ciganek et al, 1995;Zubkov et al, 2004Zubkov et al, , 2018Zaytsev et al, 2020), or on the other hand we can observe electrophilic addition of halogens to multiple bonds (Berson et al, 1954;Barlow et al, 1971;Kobayashi et al, 1976;Solov'eva et al, 1984). Halogenated organic compounds are of interest because of their photoactivity in the solid state, high solubility in halocarbons, high thermal and oxidative stability, etc., to which non-covalent halogen bonding can contribute (Afkhami et al, 2017;Maharramov et al, 2018;Mahmoudi et al, 2017Mahmoudi et al, , 2019Shixaliyev et al, 2014).…”

“…In view of its higher directionality, the halogen bond can be better suited than the hydrogen bond for the building of functional materials by non-covalent self-assembly via specific molecular interactions Kopylovich et al, 2011;Ma et al, 2017aMa et al, ,b, 2020Mahmudov et al, 2012Mahmudov et al, , 2013Mahmudov et al, , 2019Mahmudov et al, , 2020. In a previous work (Zubkov et al, 2018), the formation of a halogenated Wagner-Meervein rearrangement product under the action of molecular bromine in dry dichloromethane on isoindole 1 was shown. In this study, the effect of [(Me 2 NCOMe) 2 H] + Br 3 À (Rodygin et al, 1992;Prokop'eva et al, 2008) is reported.…”

Crystal structure and Hirshfeld surface analysis of 3-amino-5-phenylthiazolidin-2-iminium bromide

“…On the other hand, as hydrazones these N-containing ligands have been widely used in the synthesis of coordination compounds (Gurbanov et al, 2018a,b). The non-covalent donor or acceptor properties of Ncontaining ligands can also contribute to their catalytic activity, among other properties (Mahmudov et al, 2019;Zubkov et al, 2018). As part of our ongoing work in this area, we now describe the synthesis and structure of the title molecular salt, C 9 H 12 N 3 S + ÁBr À , (I).…”