Secondary Electrostatic Interaction Model Revised: Prediction Comes Mainly from Measuring Charge Accumulation in Hydrogen-Bonded Monomers

Journal of the American Chemical Society
Stephanie C C van der LubbeCélia Fonseca Guerra

Abstract

The secondary electrostatic interaction (SEI) model is often used to predict and explain relative hydrogen bond strengths of self-assembled systems. The SEI model oversimplifies the hydrogen-bonding mechanisms by viewing them as interacting point charges, but nevertheless experimental binding strengths are often in line with the model's predictions. To understand how this rudimentary model can be predictive, we computationally studied two tautomeric quadruple hydrogen-bonded systems, DDAA-AADD and DADA-ADAD. Our results reveal that when the proton donors D (which are electron-donating) and the proton acceptors A (which are electron-withdrawing) are grouped together as in DDAA, there is a larger accumulation of charge around the frontier atoms than when the proton donor and acceptor groups are alternating as in DADA. This accumulation of charge makes the proton donors more positive and the proton acceptors more negative, which enhances both the electrostatic and covalent interactions in the DDAA dimer. The SEI model is thus predictive because it provides a measure for the charge accumulation in hydrogen-bonded monomers. Our findings can be understood from simple physical organic chemistry principles and provide supramolecular ch...Continue Reading

References

Apr 1, 1995·Journal of Biomolecular Structure & Dynamics·J Florián, J Leszczyński
Sep 15, 1988·Physical Review A: General Physics·A D Becke
Jul 10, 2001·Angewandte Chemie·Leonard J. PrinsPeter Timmerman
Jul 18, 2002·Journal of the American Chemical Society·Paul L A Popelier, Laurent Joubert
Dec 4, 2003·Journal of Computational Chemistry·Célia Fonseca GuerraF Matthias Bickelhaupt
Jul 30, 2005·The Journal of Chemical Physics·Erin R Johnson, Axel D Becke
Feb 1, 1967·Proceedings of the National Academy of Sciences of the United States of America·Y KyogokuA Rich
Jan 18, 2007·Journal of the American Chemical Society·Smilja DjurdjevicFrancesco Zerbetto
Sep 15, 2009·Journal of the American Chemical Society·Barry A BlightAlexandra M Z Slawin
Feb 24, 2010·Journal of Medicinal Chemistry·Bernd KuhnMartin Stahl
Feb 22, 2011·Nature Chemistry·Andrew J Wilson
Feb 22, 2011·Nature Chemistry·Barry A BlightPatrick I T Thomson
Oct 15, 2011·Chemistry : a European Journal·Célia Fonseca GuerraF Matthias Bickelhaupt
Sep 10, 2014·Angewandte Chemie·Frank Weinhold, Roger A Klein
Feb 24, 2015·Journal of Molecular Modeling·Peter PolitzerTimothy Clark
May 6, 2015·Chemical Society Reviews·Nabarun RoyJean-Marie Lehn
Feb 4, 2016·Chemical Reviews·A Subha Mahadevi, G Narahari Sastry
May 10, 2017·Chemistry : a European Journal·Stephanie C C van der Lubbe, Célia Fonseca Guerra
May 13, 2017·Physical Chemistry Chemical Physics : PCCP·Trevor A HamlinF Matthias Bickelhaupt
Jan 23, 2018·The Journal of Physical Chemistry. a·Alice A GroschCélia Fonseca Guerra
Mar 23, 2018·Chemical Communications : Chem Comm·Chia-Hua WuJudy I Wu
Jun 14, 2018·Chemical Science·Wilmer E Vallejo NarváezTomás Rocha-Rinza
Nov 30, 2018·Physical Chemistry Chemical Physics : PCCP·Timothy ClarkPeter Politzer
Dec 13, 2018·Chemical Communications : Chem Comm·Wilmer E Vallejo NarváezTomás Rocha-Rinza

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Citations

Jan 12, 2020·Nature Protocols·Pascal VermeerenTrevor A Hamlin
Sep 26, 2020·Physical Chemistry Chemical Physics : PCCP·Justyna Dominikowska
Oct 1, 2020·Physical Chemistry Chemical Physics : PCCP·Diego M Andrada, Cina Foroutan-Nejad
Jun 27, 2019·Chemistry, an Asian Journal·Stephanie C C van der Lubbe, Célia Fonseca Guerra
Apr 8, 2020·ChemistryOpen·Anselmo Del PradoYi-Lin Wu
Dec 30, 2020·Chemistry, an Asian Journal·Olatz LarrañagaAbel de Cózar
Jan 30, 2021·Chemistry : a European Journal·Pascal VermeerenF Matthias Bickelhaupt
Apr 20, 2021·ACS Omega·Zhulu XieQichun Zhang
May 4, 2021·Wiley Interdisciplinary Reviews. Computational Molecular Science·Lucas J KarasJudy I-Chia Wu
Jul 3, 2021·Mathematical Biosciences and Engineering : MBE·Xuewei JiangJun Zhang
Oct 22, 2019·The Journal of Organic Chemistry·Xuhui LinYirong Mo
Mar 20, 2020·Journal of Agricultural and Food Chemistry·Pan TaoJie Song
Sep 29, 2020·Journal of the American Chemical Society·Hyejeong ChoiDiane K Smith
Sep 7, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Diane K Smith
Sep 17, 2021·Physical Chemistry Chemical Physics : PCCP·Daniela Rodrigues SilvaCélia Fonseca Guerra
Oct 29, 2021·ChemPlusChem·Lucas de Azevedo SantosCélia Fonseca Guerra

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Software Mentioned

Amsterdam Density Functional ( ADF )
DADA
DDAA

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