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Fluorine prefers hydrogen bonds over halogen bonds! Insights from crystal structures of some halofluorobenzenes

Dikundwar, Amol G and Sathishkumar, Ranganathan and Row, Tayur Guru N (2014) Fluorine prefers hydrogen bonds over halogen bonds! Insights from crystal structures of some halofluorobenzenes. In: ZEITSCHRIFT FUR KRISTALLOGRAPHIE, 229 (9, SI). pp. 609-624.

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Official URL: http://dx.doi.org/ 10.1515/zkri-2014-1750

Abstract

Crystal structures of a series of isomers of chlorofluorobenzene, bromofluorobenzene and iodofluorobenzene, all of which are liquids under ambient conditions, are determined by a technique of in situ cryocrystallography. These simple dihalo substituted benzenes provide clear insights into subtle interplay of packing interactions preferred by fluorine and heavier halogens for example, C-H center dot center dot center dot X hydrogen bonds vs. X center dot center dot center dot X halogen bonds (X=F, Cl, Br, I). The interaction patterns noted here are purely characteristic of halogens, having not been influenced by other stronger interactions. Variability of principal supramolecular synthons among the isomers highlights the importance of molecular shape and relative position of interacting atoms while preserving the basic intermolecular bonds. Mutually exclusive occurrence of homo (I center dot center dot center dot I) and hetero (I center dot center dot center dot F) halogen bonds in polymorphs of 4-iodofluorobenzene questions the robustness and reliability of these interactions.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the WALTER DE GRUYTER GMBH, GENTHINER STRASSE 13, D-10785 BERLIN, GERMANY
Keywords: cryocrystallography; halobenzenes; halogen bond; hydrogen bond; Organic fluorine
Department/Centre: Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Depositing User: Id for Latest eprints
Date Deposited: 20 Nov 2014 04:19
Last Modified: 20 Nov 2014 04:19
URI: http://eprints.iisc.ac.in/id/eprint/50299

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