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Establishing Halogen‐Bond Preferences in Molecules with Multiple Acceptor Sites

Establishing Halogen‐Bond Preferences in Molecules with Multiple Acceptor Sites The interplay between hydrogen bonds (HBs) and halogen bonds (XBs), has been addressed by co‐crystallizing two halogen bond donors, 1,4‐diiodotetrafluorbenzene(DITFB) and 1,3,5‐trifluoro‐2,4,6‐triiodobenzene(TITFB) with four series of targets; N‐(pyridin‐2‐yl)benzamide (Bz‐X), N‐(pyridin‐2‐yl)picolinamides (2Pyr‐X), N‐(pyridin‐2‐yl)nicotinamides (3Pyr‐X), N‐(pyridin‐2‐yl)isonicotinamides (4Pyr‐X); X=H/Cl/Br/I. The structural outcomes were compared with interactions in the targets themselves. 13 co‐crystals were analysed by single‐crystal X‐ray diffraction (SCXRD). In all three co‐crystals from the 2Pyr series, the intramolecular HB remained intact while the XB donors engaged with the N(pyr) or O=C sites. In the ten co‐crystals from the other three series, the intermolecular HBs present in the individual targets were disrupted in 9/10 cases. Overall, the acceptor sites selected by the halogen‐bond donors in these targets were distributed as follows; N(pyr)=81 %, O=C (15 %) or π (4 %). http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png ChemPlusChem Wiley

Establishing Halogen‐Bond Preferences in Molecules with Multiple Acceptor Sites

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References (29)

Publisher
Wiley
Copyright
© 2021 Wiley‐VCH GmbH
eISSN
2192-6506
DOI
10.1002/cplu.202100102
Publisher site
See Article on Publisher Site

Abstract

The interplay between hydrogen bonds (HBs) and halogen bonds (XBs), has been addressed by co‐crystallizing two halogen bond donors, 1,4‐diiodotetrafluorbenzene(DITFB) and 1,3,5‐trifluoro‐2,4,6‐triiodobenzene(TITFB) with four series of targets; N‐(pyridin‐2‐yl)benzamide (Bz‐X), N‐(pyridin‐2‐yl)picolinamides (2Pyr‐X), N‐(pyridin‐2‐yl)nicotinamides (3Pyr‐X), N‐(pyridin‐2‐yl)isonicotinamides (4Pyr‐X); X=H/Cl/Br/I. The structural outcomes were compared with interactions in the targets themselves. 13 co‐crystals were analysed by single‐crystal X‐ray diffraction (SCXRD). In all three co‐crystals from the 2Pyr series, the intramolecular HB remained intact while the XB donors engaged with the N(pyr) or O=C sites. In the ten co‐crystals from the other three series, the intermolecular HBs present in the individual targets were disrupted in 9/10 cases. Overall, the acceptor sites selected by the halogen‐bond donors in these targets were distributed as follows; N(pyr)=81 %, O=C (15 %) or π (4 %).

Journal

ChemPlusChemWiley

Published: Aug 1, 2021

Keywords: co-crystals

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