2,2'-Bipyridine Derivatives as Halogen Bond Acceptors in Multicomponent Crystals

Filip Kučas; Lidija Posavec; Vinko Nemec; Nikola Bedeković; Dominik Cinčić

doi:10.1021/acs.cgd.3c01055

2,2'-Bipyridine Derivatives as Halogen Bond Acceptors in Multicomponent Crystals

Cryst Growth Des. 2023 Nov 9;23(12):8482-8487. doi: 10.1021/acs.cgd.3c01055. eCollection 2023 Dec 6.

Authors

Filip Kučas¹, Lidija Posavec¹, Vinko Nemec¹, Nikola Bedeković¹, Dominik Cinčić¹

Affiliation

¹ Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, 10000 Zagreb, Croatia.

Abstract

In this work, we present a systematic study of the halogen bonding potential of different 2,2'-bipyridine derivatives in the synthesis of cocrystals by using selected perfluorinated iodobenzenes and N-haloimides as halogen bond donors. These halogen bond acceptor molecules were chosen to explore how different substituents on 2,2'-bipyridine affect halogen bond formation. Out of 24 combinations, we obtained only 8 cocrystals by using two methods, liquid-assisted grinding and crystallization from the solution. Of those 8 cocrystals, one has already been described in the literature. As expected, structural data revealed that 2,2'-bipyridine derivatives act as ditopic halogen bond acceptors in all structures. Dominant interactions in 7 of the cocrystals are I···N or Br···N halogen bonds, while in the one remaining cocrystal it is the I···C(π) halogen bond.