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Hydrogen bond design principles

Overview

Lucas J. Karas, Chia‐Hua Wu, Ranjita Das, Judy I‐Chia Wu

Published Online: May 16 2020

DOI: 10.1002/wcms.1477

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Abstract Hydrogen bonding principles are at the core of supramolecular design. This overview features a discussion relating molecular structure to hydrogen bond strengths, highlighting the following electronic effects on hydrogen bonding: electronegativity, steric effects, electrostatic effects, π‐conjugation, and network cooperativity. Historical developments, along with experimental and computational efforts, leading up to the birth of the hydrogen bond concept, the discovery of nonclassical hydrogen bonds (CH…O, OH…π, dihydrogen bonding), and the proposal of hydrogen bond design principles (e.g., secondary electrostatic interactions, resonance‐assisted hydrogen bonding, and aromaticity effects) are outlined. Applications of hydrogen bond design principles are presented. This article is categorized under: Structure and Mechanism > Molecular Structures Structure and Mechanism > Reaction Mechanisms and Catalysis

Secondary electrostatic interactions (SEIs) between proton donors (“D,” in orange) and acceptors (“A,” in blue) in: (a) doubly, (b) triply, and (c) quadruply hydrogen bonded arrays. Solid lines indicate attractive interactions and dashed lines indicate repulsive interactions

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Examples of other diamine‐based proton sponges: TMGN, P₂‐TPPN, t‐Bu–P₂, vinamidine, and a fluorene‐based proton sponge

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(a) The original “proton sponge,” DMAN. (b) Protonation of the diamine relieves lone pair repulsion, resulting in low‐barrier [N…H…N]⁺ hydrogen bonding

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(a) Schematic illustration of dihydrogen bonding. Dihydrogen bonds were shown to direct the (b) preassembly of covalent materials, and (c) the diastereoselectivity of borohydride reduction

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(a) Schematic illustration of XH…π interactions. (b) and (c) Examples of OH…π hydrogen bonding. (d) Example of BH…π hydrogen bonding

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(a) Schematic illustration of CH…Y interactions (Y = electronegative atom or anion). (b) F₂CH…O hydrogen bonding. (c) Examples of anion receptors based on CH…anion interactions

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Effects of electronegativity on OH…N vs. NH…N hydrogen bond strength. Explanations based on: (a) donor–acceptor orbital interactions (using water…ammonia and ammonia…ammonia as examples), and (b) dipole–dipole interactions

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Depictions of hydrogen bonding, in (a) H₂OH₂O and (b) ammonium hydroxide, based on the early works of Latimer and Rodebush¹

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Timeline for the development of hydrogen bond design principles

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(a) Hydrogen bonding networks in the active site of triosephosphate isomerase. (b) Cooperative hydrogen bonds can stabilize the conjugate base of OH substituted benzoic acid (note pK_a values for the acid). (c) Example of a covalent polyol system. (d) Enhanced hydrogen bonding resulting from neutral, short‐range networks (see OH group in bold)

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(a) Aromaticity gain and loss in hydrogen‐bonded heterocycles, and (b) a reversed effect in photoexcited states

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Resonance structures showing the effects of aromaticity gain in (a) tropolone, and in hydrogen‐bonded (b) squaramide and C) guanine

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(a) Intramolecular and intermolecular resonance‐assisted hydrogen bonding (RAHB) in β‐diketone. (b) Possible RAHB effects in hydrogen‐bonded dimers and base pairs

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Examples of quadruply hydrogen bonded arrays prepared based on the secondary electrostatic interaction (SEI) model. (a) 2‐Ureido‐4‐pyrimidone,⁶⁷ and (b) Blight's AAAA‐DDDD array⁶⁸

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