Non-covalent interactions in molecular systems: thermodynamic evaluation of the hydrogen bond strength in aminoalcohols

2021 ◽  
Author(s):  
Riko Siewert ◽  
Ralf Ludwig ◽  
Sergey P. Verevkin
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Bond Strength ◽  
Functional Groups ◽  
Thermodynamic Evaluation ◽  
Molecular Systems ◽  
Hydrogen Bond Strength ◽  
Non Covalent Interactions ◽  
Intramolecular Hydrogen ◽  
Covalent Interactions

In molecules with two functional groups that form hydrogen bonds, the strength of intramolecular hydrogen bonds does not depend significantly on the structure.

Intramolecular Hydrogen Bonds and Fermi Resonance in N-Substituted N'-(2-Fluorobenzoyl)thiourea Derivatives

1994 ◽  
Vol 59 (4) ◽  
pp. 951-956 ◽  
Author(s):  
Oľga Hritzová ◽  
Dušan Koščík
Keyword(s):  
Hydrogen Bond ◽  
Perturbation Theory ◽  
Hydrogen Bonds ◽  
Bond Strength ◽  
Infrared Spectra ◽  
Fermi Resonance ◽  
Absorption Bands ◽  
Thiourea Derivatives ◽  
Hydrogen Bond Strength ◽  
Intramolecular Hydrogen

The presence of intramolecular NH...O=C bonds was proved in N-substituted N'-(2-fluorobenzoyl)thiourea derivatives by analysis of their infrared spectra. The intramolecular vibrational effects bring about a shift of the ν(NH) vibrational band to lower frequencies to the extent that the band gets into a vicinity to the δ(NH) overtone and Fermi resonance occurs between them. In addition, the ν(NH) vibration is also affected by Fermi resonance with the ν(CO) + δ(NH) combination. Double absorption bands were observed in the ν(CO) region for some of the derivatives. Based on perturbation theory applied to three-level interactions and using the Langseth and Lord equations, the band frequencies corrected for Fermi resonance were calculated and the hydrogen bond strength was examined in the compounds studied.

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.

scholarly journals New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation

2016 ◽  
Vol 12 ◽  
pp. 2834-2848 ◽  
Author(s):  
Pavel Nagorny ◽  
Zhankui Sun
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Recent Progress ◽  
Halogen Bonds ◽  
Hydrogen Bond Donor ◽  
New Approaches ◽  
Substrate Activation ◽  
Non Covalent Interactions ◽  
Covalent Interactions ◽  
Hydrogen Bond Donors

Hydrogen bond donor catalysis represents a rapidly growing subfield of organocatalysis. While traditional hydrogen bond donors containing N–H and O–H moieties have been effectively used for electrophile activation, activation based on other types of non-covalent interactions is less common. This mini review highlights recent progress in developing and exploring new organic catalysts for electrophile activation through the formation of C–H hydrogen bonds and C–X halogen bonds.

Intramolecular Hydrogen Bond Strength and pKaDetermination ofN,N‘-Disubstituted Imidazole-4,5-dicarboxamides

2005 ◽  
Vol 7 (1) ◽  
pp. 135-138 ◽  
Author(s):  
Jeremy R. Rush ◽  
Stacey L. Sandstrom ◽  
Jianqing Yang ◽  
Rebecca Davis ◽  
Om Prakash ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Bond Strength ◽  
Intramolecular Hydrogen Bond ◽  
Hydrogen Bond Strength ◽  
Intramolecular Hydrogen

Computational evidence that hyperconjugative orbital interactions are responsible for the stability of intramolecular Te⋯O/Te⋯S non-covalent interactions and comparable to hydrogen bonds in quasi-cyclic systems

2016 ◽  
Vol 40 (11) ◽  
pp. 9132-9138 ◽  
Author(s):  
Mrinal Kanti Si ◽  
Bishwajit Ganguly
Keyword(s):  
Hydrogen Bonds ◽  
Bond Strength ◽  
Orbital Interactions ◽  
Non Covalent Interactions ◽  
Cyclic Systems ◽  
The Stability ◽  
Covalent Interactions ◽  
Secondary Bonding

The intramolecular secondary bonding interactions involving quasi-cyclic tellurium are comparable to H-bond strength and partially governed by orbital interactions.

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