DFT study of the hydrogen bond strength and IR spectra of formic, oxalic, glyoxylic and pyruvic acids in vacuum, acetone and water solution

2009 ◽  
Vol 22 (10) ◽  
pp. 933-947 ◽  
Author(s):  
Giuseppe Buemi
Keyword(s):  
Hydrogen Bond ◽  
Bond Strength ◽  
Ir Spectra ◽  
Water Solution ◽  
Dft Study ◽  
Hydrogen Bond Strength ◽  
Pyruvic Acids

Redshift or Adduct Stabilization—A Computational Study of Hydrogen Bonding in Adducts of Protonated Carboxylic Acids

2009 ◽  
Vol 15 (2) ◽  
pp. 239-248 ◽  
Author(s):  
Solveig Gaarn Olesen ◽  
Steen Hammerum
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Bond Strength ◽  
Bond Length ◽  
Carboxylic Acids ◽  
Computational Study ◽  
Proton Affinities ◽  
Oh Groups ◽  
Hydrogen Bond Strength ◽  
Length Changes

It is generally expected that the hydrogen bond strength in a D–H•••A adduct is predicted by the difference between the proton affinities (Δ PA) of D and A, measured by the adduct stabilization, and demonstrated by the infrared (IR) redshift of the D–H bond stretching vibrational frequency. These criteria do not always yield consistent predictions, as illustrated by the hydrogen bonds formed by the E and Z OH groups of protonated carboxylic acids. The Δ PA and the stabilization of a series of hydrogen bonded adducts indicate that the E OH group forms the stronger hydrogen bonds, whereas the bond length changes and the redshift favor the Z OH group, matching the results of NBO and AIM calculations. This reflects that the thermochemistry of adduct formation is not a good measure of the hydrogen bond strength in charged adducts, and that the ionic interactions in the E and Z adducts of protonated carboxylic acids are different. The OH bond length and IR redshift afford the better measure of hydrogen bond strength.

Water’s Hydrogen Bond Strength

2010 ◽  
pp. 69-86 ◽  
Author(s):  
Martin Chaplin
Keyword(s):  
Hydrogen Bond ◽  
Bond Strength ◽  
Hydrogen Bond Strength
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