Halogen vs. hydrogen bonding

This article is HOT as recommended by the referees. And we’ve made it free to access for 4 weeks.

Competing hydrogen-bond and halogen-bond donors in crystal engineering

Competing hydrogen-bond and halogen-bond donors in crystal engineering

In this HOT article by Aakeröy et al, relevant hydrogen-bond and halogen-bond acceptors and donors were selected to study the competition between these two molecular interactions in supramolecular assembly.  Twelve co-crystals were synthesized based on two different azobipyridines as acceptors and six donor molecules possessing both hydrogen-bond and halogen-bond moieties.  The key conclusions which could be drawn from the study were: (i) the hydrogen-bond is the principal driving force in the formation of 3,3′-azabipyridine co-crystals whereas hydrogen and halogen bonds do indeed compete in the formation of the 4,4′-azabipyridine co-crystals; (ii) the iodine donor appears to be a better halogen-bond donor than bromine; and  (iii) the three different hydrogen-bond donors studied (–COOH, –OH and –CN(R)OH) behave similarly.

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Competing hydrogen-bond and halogen-bond donors in crystal engineering
Christer B. Aakeröy ,  Sheelu Panikkattu ,  Prashant D. Chopade and John Desper
CrystEngComm, 2013, Advance Article
DOI: 10.1039/C2CE26747K

This article will be published in a forthcoming themed issue on Halogen bonding, other highlights include:

Iodo-imidazolium salts: halogen bonding in crystals and anion-templated pseudorotaxanes
Antonio Caballero,  Sam Bennett,  Christopher J. Serpell and Paul D. Beer
CrystEngComm, 2013, Advance Article
DOI: 10.1039/C2CE26020D

Halogen bonding at work: recent applications in synthetic chemistry and materials science
Franck Meyer and Philippe Dubois
CrystEngComm, 2013, Advance Article
DOI: 10.1039/C2CE26150B

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