Theoretical calculations, examination of crystallographic data, and experimental binding energies suggest that even in the absence of electron withdrawing substituents, simple arenes such as benzene form hydrogen bonds with anions that can exceed 50% of the strength of those formed by O–H and N-H groups. Thus, when present in a receptor, even moderately acidic C–H groups can significantly enhance the anion binding affinity and they should be considered as additional binding sites within the host cavity.
Revised: August 17, 2005 |
Published: June 15, 2005
Citation
Bryantsev V., and B.P. Hay. 2005.Are C–H Groups Significant Hydrogen Bonding Sites in Anion Receptors? Benzene Complexes with Cl—, NO3—, and ClO4—.Journal of the American Chemical Society 127, no. 23:8282-8283.PNNL-SA-44595.doi:10.1021/ja0518272