Structural Chemistry

, Volume 28, Issue 2, pp 371–378

How weak an acid can be? Variations of H-bond and/or van der Waals Interaction of Weak Acids

  • Szebasztián Szaniszló
  • Imre G. Csizmadia
  • András Perczel
Original Research

DOI: 10.1007/s11224-016-0888-5

Cite this article as:
Szaniszló, S., Csizmadia, I.G. & Perczel, A. Struct Chem (2017) 28: 371. doi:10.1007/s11224-016-0888-5
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Abstract

Complex formation ability and stability of both weak and super-weak acids was studied by mean of in silico determined thermodynamic data of the complexes. While weak acids act like Brønsted acids forming hydrogen bond type Brønsted complexes, super-weak acids form Lewis complexes via van der Waals interaction. Unlike in the former type, upon complexation, C-H distances changes insignificantly, yet the complex formation is energy driven in the terms of zero-point corrected Energies, ΔEzp < 0 kcal mol−1, which supports the Lewis complex formation, with the exception of CH4, an extremely “weak acid”.

Graphical abstract

Selected NBOs of the complexes formed between NC-CH2-H (Lewis acid) with dioxolane as well as NC-O-H (Brønsted acid) and dioxolane.

Keywords

Acidssuper-weak acidsC-H hydrogen bondLewis acid and complexBrønsted acid and complex

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • Szebasztián Szaniszló
    • 1
  • Imre G. Csizmadia
    • 2
  • András Perczel
    • 1
    • 3
  1. 1.Laboratory of Structural Chemistry and Biology, Institute of ChemistryEötvös Loránd UniversityBudapestHungary
  2. 2.Department of ChemistryUniversity of TorontoTorontoCanada
  3. 3.MTA-ELTE, Protein Modelling Research GroupBudapestHungary