Heterocyclic 1,3‐diazepine‐based thiones and selones as versatile halogen‐bond acceptors

Utilizing the N‐heterocyclic chalcogenones hexahydro‐1,3‐bis(2,4,6‐trimethylphenyl)‐2H‐1,3‐diazepine‐2‐thione (SDiazMesS) and hexahydro‐1,3‐bis(2,4,6‐trimethylphenyl)‐2H‐1,3‐diazepine‐2‐selone (SDiazMesSe) as halogen‐bond acceptors, a total of 24 new cocrystals were prepared. The solid‐state structu...

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Veröffentlicht in:Acta crystallographica Section B, Structural science, crystal engineering and materials Structural science, crystal engineering and materials, 2022-10, Vol.78 (5), p.745-755
Hauptverfasser: Ragusa, Arianna C., Peloquin, Andrew J., Shahani, Marjan M., Dowling, Keri N., Golen, James A., McMillen, Colin D., Rabinovich, Daniel, Pennington, William T.
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container_title Acta crystallographica Section B, Structural science, crystal engineering and materials
container_volume 78
creator Ragusa, Arianna C.
Peloquin, Andrew J.
Shahani, Marjan M.
Dowling, Keri N.
Golen, James A.
McMillen, Colin D.
Rabinovich, Daniel
Pennington, William T.
description Utilizing the N‐heterocyclic chalcogenones hexahydro‐1,3‐bis(2,4,6‐trimethylphenyl)‐2H‐1,3‐diazepine‐2‐thione (SDiazMesS) and hexahydro‐1,3‐bis(2,4,6‐trimethylphenyl)‐2H‐1,3‐diazepine‐2‐selone (SDiazMesSe) as halogen‐bond acceptors, a total of 24 new cocrystals were prepared. The solid‐state structures of the parent molecules were also determined, along with those of their acetonitrile solvates. Through the reaction of the chalcogen atom with molecular diiodine, a variety of S—I—I and Se—I—I fragments were formed, spanning a wide range of I—I bond orders. With acetone as a reaction solvent, molecular diiodine causes the oxidative addition of acetone to the chalcogen atom, resulting in new C—S, C—Se and C—C covalent bonds under mild conditions. The common halogen‐bond donors, iodopentafluorobenzene, 1,2‐, 1,3‐ and 1,4‐diiodotetrafluorobenzene, 1,3,5‐trifluorotriiodobenzene and tetraiodoethylene resulted in halogen‐bond‐driven cocrystal formation. In most cases, the analogous SDiazMesS and SDiazMesSe cocrystals are isomorphic. Utilizing the N‐heterocyclic chalcogenones hexahydro‐1,3‐bis(2,4,6‐trimethylphenyl)‐2H‐1,3‐diazepine‐2‐thione (SDiazMesS) and hexahydro‐1,3‐bis(2,4,6‐trimethylphenyl)‐2H‐1,3‐diazepine‐2‐selone (SDiazMesSe) as halogen‐bond acceptors, 24 new cocrystals were prepared. The solid‐state structures of the parent molecules were also determined, along with those of their acetonitrile solvates.
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subjects Acetone
Acetonitrile
cocrystal
Covalent bonds
diiodine
halogen bonding
organoiodine
selone
thione
title Heterocyclic 1,3‐diazepine‐based thiones and selones as versatile halogen‐bond acceptors
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