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Halogen bonding in solution

Kapitel i bok
Författare Anna-Carin Carlsson
Alberte X. Veiga
Mate Erdelyi
Publicerad i Halogen Bonding II. Impact on Materials Chemistry and Life Sciences. Pierangelo Metrangolo, Giuseppe Resnati (eds.)
Volym 359
Sidor 49-76
ISBN 978-3-319-15731-3
ISSN 0340-1022
Förlag Springer
Publiceringsår 2015
Publicerad vid Institutionen för kemi och molekylärbiologi
Sidor 49-76
Språk en
Länkar dx.doi.org/10.1007/128_2014_607
Ämnesord halogen bond, solution, NMR, symmetry
Ämneskategorier Kemi, Organisk kemi, Fysikalisk organisk kemi, Läkemedelskemi

Sammanfattning

Because of its expected applicability for modulation of molecular recognition phenomena in chemistry and biology, halogen bonding has lately attracted rapidly increasing interest. As most of these processes proceed in solution, the understanding of the influence of solvents on the interaction is of utmost importance. In addition, solution studies provide fundamental insights into the nature of halogen bonding, including, for example, the relative importance of charge transfer, dispersion, and electrostatics forces. Herein, a selection of halogen bonding literature is reviewed with the discussion focusing on the solvent effect and the electronic characteristics of halogen bonded complexes. Hence, charged and neutral systems together with two- and three-center bonds are presented in separate sub-sections. Solvent polarity is shown to have a slight stabilizing effect on neutral, two-center halogen bonds while strongly destabilizes charged, two-center complexes. It does not greatly influence the geometry of three-center halogen bonds, even though polar solvents facilitate dissociation of the counter-ion of charged three-center bonds. The charged three-center bonds are strengthened by increased environment polarity. Solvents possessing hydrogen bond donor functionalities efficiently destabilize all types of halogen bonds, primarily because of halogen vs hydrogen bond competition. A purely electrostatic model is insufficient for the description of halogen bonds in polar systems whereas it may give reasonable correlation to experimental data obtained in noninteracting, apolar solvents. Whereas dispersion plays a significant role for neutral, two-center halogen bonds, charged halogen bond complexes possess a significant charge transfer characteristic.

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