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Synthetic Approaches to Halogen Bonded Ternary Cocrystals
Author(s) -
Jain Harsh,
Sutradhar Dipankar,
Roy Sourav,
Desiraju Gautam R.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202103516
Subject(s) - cocrystal , synthon , halogen bond , halogen , ternary operation , nucleophile , electrophile , hydrogen bond , supramolecular chemistry , chemistry , crystal engineering , combinatorial chemistry , materials science , organic chemistry , molecule , catalysis , computer science , alkyl , programming language
Abstract Higher cocrystal synthesis depends acutely on a knowledge of supramolecular synthons. We report three synthetic approaches towards ternary halogen bonded cocrystals that illustrate specificity and generality. Electrophilicity/nucleophilicity differences are needed among alternative sites of halogen bond formation. The two halogen bonds A⋅⋅⋅B and B⋅⋅⋅C in a halogen bonded ternary cocrystal ABC need to be of different strength. Interaction mimicry of hydrogen bonds by halogen bonds is a viable approach towards ternaries as illustrated with the pyrene structure. Finally, the crystal engineer should well be able to anticipate halogen bonds that are stronger than hydrogen bonds.