Crystals (Jan 2021)

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

  • Atash V. Gurbanov,
  • Dmitriy F. Mertsalov,
  • Fedor I. Zubkov,
  • Maryana A. Nadirova,
  • Eugeniya V. Nikitina,
  • Hieu H. Truong,
  • Mikhail S. Grigoriev,
  • Vladimir P. Zaytsev,
  • Kamran T. Mahmudov,
  • Armando J. L. Pombeiro

DOI
https://doi.org/10.3390/cryst11020112
Journal volume & issue
Vol. 11, no. 2
p. 112

Abstract

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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.

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