1,4-Dibromo-2,5-bis(phenylalkoxy)benzene Derivatives: C–Br...π(arene) <i>Versus</i> C–H...Br and Br...Br Interactions in the Solid State

1,4-Dibromo-2,5-bis(phenylalkoxy)benzene Derivatives: C–Br...π(arene) <i>Versus</i> C–H...Br and Br...Br Interactions in the Solid State

We have prepared and characterized 1,4-dibromo-2,5-bis(2-phenylethoxy)benzene (<b>1</b>) and 1,4-dibromo-2,5-bis(3-phenylpropoxy)benzene (<b>2</b>). Their single-crystal structures confirm that, at the molecular level, they are similar with the phenylalkoxy chains in extended...

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Main Authors: Giacomo Manfroni, Alessandro Prescimone, Edwin C. Constable, Catherine E. Housecroft
Format: Article
Language:English
Published: MDPI AG 2021-03-01
Series:Crystals
Subjects:
bromine
crystal structure
intermolecular interactions
packing interactions
Online Access:https://www.mdpi.com/2073-4352/11/4/325
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spelling doaj-80cca5d14a0c4cd8aaeb98cf2e04da112021-03-26T00:00:11ZengMDPI AGCrystals2073-43522021-03-011132532510.3390/cryst110403251,4-Dibromo-2,5-bis(phenylalkoxy)benzene Derivatives: C–Br...π(arene) <i>Versus</i> C–H...Br and Br...Br Interactions in the Solid StateGiacomo Manfroni0Alessandro Prescimone1Edwin C. Constable2Catherine E. Housecroft3Department of Chemistry, University of Basel, BPR 1096, Mattenstrasse 24a, CH-4058 Basel, SwitzerlandDepartment of Chemistry, University of Basel, BPR 1096, Mattenstrasse 24a, CH-4058 Basel, SwitzerlandDepartment of Chemistry, University of Basel, BPR 1096, Mattenstrasse 24a, CH-4058 Basel, SwitzerlandDepartment of Chemistry, University of Basel, BPR 1096, Mattenstrasse 24a, CH-4058 Basel, SwitzerlandWe have prepared and characterized 1,4-dibromo-2,5-bis(2-phenylethoxy)benzene (<b>1</b>) and 1,4-dibromo-2,5-bis(3-phenylpropoxy)benzene (<b>2</b>). Their single-crystal structures confirm that, at the molecular level, they are similar with the phenylalkoxy chains in extended conformations. However, there are significant differences in packing interactions. The packing in <b>1</b> is dominated by C–Br...π(arene) interactions, with each Br located over one C–C bond of the central arene ring of an adjacent molecule. In contrast, the packing of molecules of <b>2</b> involves a combination of C–H...Br hydrogen bonds, Br...Br interactions, and arene–arene π-stacking. The single-crystal structures of both orthorhombic and triclinic polymorphs of <b>1</b> have been determined and the packing interactions are shown to be essentially identical.https://www.mdpi.com/2073-4352/11/4/325brominecrystal structureintermolecular interactionspacking interactions
collection DOAJ
language English
format Article
sources DOAJ
author Giacomo Manfroni
Alessandro Prescimone
Edwin C. Constable
Catherine E. Housecroft
spellingShingle Giacomo Manfroni
Alessandro Prescimone
Edwin C. Constable
Catherine E. Housecroft
1,4-Dibromo-2,5-bis(phenylalkoxy)benzene Derivatives: C–Br...π(arene) <i>Versus</i> C–H...Br and Br...Br Interactions in the Solid State
Crystals
bromine
crystal structure
intermolecular interactions
packing interactions
author_facet Giacomo Manfroni
Alessandro Prescimone
Edwin C. Constable
Catherine E. Housecroft
author_sort Giacomo Manfroni
title 1,4-Dibromo-2,5-bis(phenylalkoxy)benzene Derivatives: C–Br...π(arene) <i>Versus</i> C–H...Br and Br...Br Interactions in the Solid State
title_short 1,4-Dibromo-2,5-bis(phenylalkoxy)benzene Derivatives: C–Br...π(arene) <i>Versus</i> C–H...Br and Br...Br Interactions in the Solid State
title_full 1,4-Dibromo-2,5-bis(phenylalkoxy)benzene Derivatives: C–Br...π(arene) <i>Versus</i> C–H...Br and Br...Br Interactions in the Solid State
title_fullStr 1,4-Dibromo-2,5-bis(phenylalkoxy)benzene Derivatives: C–Br...π(arene) <i>Versus</i> C–H...Br and Br...Br Interactions in the Solid State
title_full_unstemmed 1,4-Dibromo-2,5-bis(phenylalkoxy)benzene Derivatives: C–Br...π(arene) <i>Versus</i> C–H...Br and Br...Br Interactions in the Solid State
title_sort 1,4-dibromo-2,5-bis(phenylalkoxy)benzene derivatives: c–br...π(arene) <i>versus</i> c–h...br and br...br interactions in the solid state
publisher MDPI AG
series Crystals
issn 2073-4352
publishDate 2021-03-01
description We have prepared and characterized 1,4-dibromo-2,5-bis(2-phenylethoxy)benzene (<b>1</b>) and 1,4-dibromo-2,5-bis(3-phenylpropoxy)benzene (<b>2</b>). Their single-crystal structures confirm that, at the molecular level, they are similar with the phenylalkoxy chains in extended conformations. However, there are significant differences in packing interactions. The packing in <b>1</b> is dominated by C–Br...π(arene) interactions, with each Br located over one C–C bond of the central arene ring of an adjacent molecule. In contrast, the packing of molecules of <b>2</b> involves a combination of C–H...Br hydrogen bonds, Br...Br interactions, and arene–arene π-stacking. The single-crystal structures of both orthorhombic and triclinic polymorphs of <b>1</b> have been determined and the packing interactions are shown to be essentially identical.
topic bromine
crystal structure
intermolecular interactions
packing interactions
url https://www.mdpi.com/2073-4352/11/4/325
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AT edwincconstable 14dibromo25bisphenylalkoxybenzenederivativescbrpareneiversusichbrandbrbrinteractionsinthesolidstate
AT catherineehousecroft 14dibromo25bisphenylalkoxybenzenederivativescbrpareneiversusichbrandbrbrinteractionsinthesolidstate
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