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Issue 28, 2018
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Aromaticity gain increases the inherent association strengths of multipoint hydrogen-bonded arrays

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Abstract

Textbook explanations for the associations of multipoint hydrogen-bonded arrays have long hinged on the secondary electrostatic interaction (SEI) model, which suggests that array association strengths depend on the proton donor (D) and acceptor (A) patterns of the interacting units. Here, computational results based on the block-localized wavefunction (BLW) method reveal limitations of the SEI model, demonstrating instead that, in the gas-phase (and in implicit chloroform solvation), the inherent free-energies of associations of multipoint hydrogen-bonded arrays correlate with the degree of “aromaticity gain” (i.e., the amount of increased cyclic π-electron delocalization) in arrays upon complexation. Excellent correlations for 46 triply (r = 0.940) and quadruply (r = 0.959) hydrogen-bonded arrays are presented.

Graphical abstract: Aromaticity gain increases the inherent association strengths of multipoint hydrogen-bonded arrays

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Publication details

The article was received on 17 Jan 2018, accepted on 13 Mar 2018 and first published on 14 Mar 2018


Article type: Communication
DOI: 10.1039/C8CC00422F
Citation: Chem. Commun., 2018,54, 3512-3515
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    Aromaticity gain increases the inherent association strengths of multipoint hydrogen-bonded arrays

    C. Wu, Y. Zhang, K. van Rickley and J. I. Wu, Chem. Commun., 2018, 54, 3512
    DOI: 10.1039/C8CC00422F

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