Role of Halogen Substituents on Halogen Bonding in 4,5-DiBromohexahydro-3a,6-Epoxyisoindol-1(4H)-ones

Abstract

A series of 4,5-dibromo-2-(4-substituted phenyl)hexahydro-3a,6-epoxyisoindol-1(4H)-ones were synthesized by reaction of the corresponding 2-(4-substituted phenyl)-2,3,7,7a-tetrahydro-3a,6-epoxyisoindol-1(6H)-ones with [(Me2NCOMe)2H]Br3 in dry chloroform under reflux for 3−5 h. In contrast to the 4-F and 4-Cl substituents, one of the bromine atoms of the isoindole moiety behaves as a halogen bond donor in the formation of intermolecular halogen bonding in the 4-H, 4-Br and 4-I analogues. Not only intermolecular hydrogen bonds, but also Ha⋯Ha and Ha⋯π types of halogen bonds in the 4-H, 4-Br, and 4-I compounds, contribute to the formation of supramolecular architectures leading to 2D or 3D structures.

Crystal structure and Hirshfeld surface analysis of (2E)-1-phenyl-3-(1H-pyrrol-2-yl)propen-1-one

“…Synthetic organic chemistry is growing tremendously, with recently developed aromatic systems that are designed for various research and commercial purposes (Maharramov et al, 2021(Maharramov et al, , 2022Erenler et al, 2022). Nowadays, five-and six-membered heterocyclic systems find broad applications in different branches of chemistry, as well as coordination chemistry (Gurbanov et al, 2021;Mahmoudi et al, 2021), drug design and development (Donmez & Turkyılmaz, 2022;Askerova, 2022), and materials science (Vela ´squez et al, 2019;Afkhami et al, 2019). The pyrrole motif is the most widespread five-membered heteroaromatic ring system in nitrogen heterocycles (Mahmoudi et al, 2017).…”

Crystal structure and Hirshfeld surface analysis of 4-(2-chloroethyl)-5-methyl-1,2-dihydropyrazol-3-one

“…Synthetic chemistry is growing extensively with recently developed heterocyclic systems for various research and commercial purposes (Maharramov et al, 2021(Maharramov et al, , 2022Erenler et al, 2022;Akkurt et al, 2023). These systems have found wide applications in diverse branches of chemistry, including the chemistry of coordination compounds (Gurbanov et al, 2021;Mahmoudi et al, 2021), drug development (Donmez & Turkyılmaz, 2022; Figure 1 The biological activities of compounds incorporating the pyrazole motif. Askerova, 2022) and material science (Vela ´squez et al, 2019;Afkhami et al, 2019).…”

Crystal structure and Hirshfeld surface analysis of (2Z)-3-oxo-N-phenyl-2-[(1H-pyrrol-2-yl)methylidene]butanamide monohydrate

“…Organic synthesis is developing enormously with newer aromatic compounds having been obtained for diverse medicinal and commercial purposes (Maharramov et al, 2021;Poustforoosh et al, 2022;Gurbanov et al, 2022a,b). Nowadays, the application of five and sixmembered heterocycles in particular has been expanded in different branches of chemistry, including coordination chemistry (Gurbanov et al, 2021;Mahmoudi et al, 2021), drug design and development (C ¸elik et al, 2023) and material science (Vela ´squez et al, 2019;Afkhami et al, 2019). The pyrrole core is the most common five-membered heteroaromatic ring system in nitrogen heterocycles (Mahmoudi et al, 2017).…”