Communication

Benzene-, Pyrrole-, and Furan-Containing Diametrically Strapped Calix[4]pyrroles—An Experimental and Theoretical Study of Hydrogen-Bonding Effects in Chloride Anion Recognition†

  1. Dae-Wi Yoon Dr.1,
  2. Dustin E. Gross1,
  3. Vincent M. Lynch Dr.1,
  4. Jonathan L. Sessler Prof.1,
  5. Benjamin P. Hay Dr.2,
  6. Chang-Hee Lee Prof.3

Article first published online: 2 JUN 2008

DOI: 10.1002/anie.200801426

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 47, Issue 27, pages 5038–5042, June 23, 2008

Additional Information

How to Cite

Yoon, D.-W., Gross, Dustin E., Lynch, Vincent M., Sessler, Jonathan L., Hay, Benjamin P. and Lee, C.-H. (2008), Benzene-, Pyrrole-, and Furan-Containing Diametrically Strapped Calix[4]pyrroles—An Experimental and Theoretical Study of Hydrogen-Bonding Effects in Chloride Anion Recognition. Angew. Chem. Int. Ed., 47: 5038–5042. doi: 10.1002/anie.200801426

Author Information

  1. 1

    Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712 (USA), Fax: (+1) 512-471-7550

  2. 2

    Chemical Sciences Division, Oak Ridge National Laboratory, Oak Ridge, TN 37830-6119 (USA)

  3. 3

    Department of Chemistry and Vascular System Research Center, Kangwon National University, Chun-Chon 200-701 (Korea)

  1. †

    This work was supported by the NIH (grant GM 58908 to J.L.S.), the Korea Research Foundation Grant funded by the Korean Government (MOEHRD) (KRF-2006-214-C00047 to D.-W.Y.), and the Korea Science and Engineering Foundation (grant no. R01-2006-000-10001-0 to C.-H.L.), and B.P.H. acknowledges support from the Division of Chemical Sciences, Geosciences, and Biosciences, Office of Basic Energy Sciences, US Department of Energy (DOE) under contract number DE-AC05-00OR22725 with Oak Ridge National Laboratory (managed by UT-Battelle, LLC).

Publication History

  1. Issue published online: 16 JUN 2008
  2. Article first published online: 2 JUN 2008
  3. Manuscript Received: 26 MAR 2008

Funded by

  • NIH. Grant Number: GM 58908
  • Korean Government. Grant Number: KRF-2006-214-C00047
  • Korea Science and Engineering Foundation. Grant Number: R01-2006-000-10001-0
  • US Department of Energy (DOE). Grant Number: DE-AC05-00OR22725

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Keywords:

  • anions;
  • calorimetry;
  • hydrogen bonds;
  • molecular modeling;
  • supramolecular chemistry
Thumbnail image of graphical abstract

Weak but important: The chloride anion binding properties of diametrically strapped calixpyrroles bearing benzene (see structure), pyrrole, and furan moieties in the strap have been studied in the solid state, in solution, and through theoretical analyses. The results obtained provide support for the notion that C[BOND]H⋅⋅⋅Cl− hydrogen bonds are significant and contribute substantially to the Cl− binding energetics.

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