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Controlling Supramolecular Assembly Using Electronic Effects

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Electronic Effects in Organic Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 351))

Abstract

Through systematic structural studies using custom designed probe molecules, it has been shown that the balance between hydrogen-bonds in the context of supramolecular chemistry and crystal engineering can be understood and guided by a semiquantitative thermodynamic assessment that integrates theoretical and experimental views of solution-based molecular recognition events. Although pKa values can be used for ranking hydrogen-bond donors/acceptors within a family of compounds, they do not offer reliable information when comparing different functional groups. However, against a backdrop of a simple electrostatic interpretation of hydrogen bonds coupled with a focus on the primary non-covalent interactions, molecular electrostatic potential surfaces can be employed for guiding the synthesis of binary- and ternary co-crystals with the desired connectivity and dimensionality.

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Notes

  1. 1.

    For an up-to-date discussion of hydrogen-bond nomenclature, see the IUPAC Project: “Categorizing hydrogen bonding and other intermolecular interactions,” http://www.iupac.org/web/ins/2004-026-2-100.

  2. 2.

    The two ligands shown in Scheme 5 were constructed using Spartan ’04 (Wavefunction. Inc Irvine, CA). Their molecular geometries were optimized using AM1, and the maxima and minima in the molecular electrostatic potential surface. (0.002 e/au isosurface) were determined using a positive point charge in vacuum as the probe.

  3. 3.

    pKa values were obtained through calculations of the conjugate acids. The calculations were carried out using ACD/Solaris version 476, Advanced Chemistry Development, Inc. Toronto, ON, Canada, www.acdlabs.com, 1994–2005.

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Author information

Authors and Affiliations

  1. Department of Chemistry, Kansas State University, Manhattan, KS, 66506, USA

    Christer B. Aakeröy & Kanishka Epa

Authors
  1. Christer B. Aakeröy
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  2. Kanishka Epa
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Corresponding author

Correspondence to Christer B. Aakeröy .

Editor information

Editors and Affiliations

  1. Universität Bonn, Institut für Physikalische und Theoretische Chemie, Bonn

    Barbara Kirchner

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Aakeröy, C.B., Epa, K. (2011). Controlling Supramolecular Assembly Using Electronic Effects. In: Kirchner, B. (eds) Electronic Effects in Organic Chemistry. Topics in Current Chemistry, vol 351. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2011_155

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