Are C-H Groups Significant Hydrogen Bonding Sites in Anion Receptors? Benzene Complexes with Cl-, NO3-, and ClO4-

J. Am. Chem. Soc., 127 (23), 8282 -8283, 2005. 10.1021/ja0518272 S0002-7863(05)01827-5
Web Release Date: May 21, 2005

Are C-H Groups Significant Hydrogen Bonding Sites in Anion Receptors? Benzene Complexes with Cl^-, NO₃^-, and ClO₄^-

Vyacheslav S. Bryantsev and Benjamin P. Hay*

Chemical Sciences Division, Pacific Northwest National Laboratory, P.O. Box 999, Richland, Washington 99352

ben.hay@pnl.gov

Received March 22, 2005

Abstract:

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.

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