The Hydrogen Bond between Oxygen Atoms in Some Organic Compounds

Hilbert, Guido E.; Wulf, Oliver R.; Hendricks, S. B.; Liddel, Urner

doi:10.1021/ja01295a002

Cited by 84 publications

(36 citation statements)

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“…Thus, the hydrogen bond provides special promise for the study of such interactions. It has been known for a long time (Hubert et al 1936;Ellis and Bath 1940) that the observed stretching frequency of a covalently bound hydrogen atom is perturbed in a specific way when that atom gets involved in hydrogen bonding to an acceptor group. These infrared shifts have given us a broad knowledge of the structural requirements for hydrogen bonding, both at inter-and intramolecular levels Marchessault 1959 a, 1959b;Marchessault and Liang 1960).…”

Section: Resultsmentioning

confidence: 99%

Changes in H-Bonding of Cellulose During Solvent Purification Treatment (Acetonation)

Awadel-Karim¹,

Leclerc²,

Grondey³

et al. 1998

Holzforschung

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Section: Resultsmentioning

confidence: 99%

Changes in H-Bonding of Cellulose During Solvent Purification Treatment (Acetonation)

Awadel-Karim¹,

Leclerc²,

Grondey³

et al. 1998

Holzforschung

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“…According to Pimentel and McClellan, the peak corresponding to the X-H stretch in the IR spectrum offers the "most sensitive, the most characteristic and one of the most informative manifestation of H bond". Hilbert et al had concluded in 1936 that following the hydrogen bond formation, the X-H stretching peak disappears from the spectrum [119]. Shortly thereafter, Badger and Bauer [120] showed that the X-H stretching peak does not disappear but gets red-shifted to a lower wave number, the shift correlating with the strength of the hydrogen bond in X-HؒؒؒY [11,120].…”

Section: Spectroscopic Evidencementioning

confidence: 99%

“…Iogansen has shown the strong correlation between hydrogen-bonding energy and the increase in intensity of XH stretching band [38]. Conversely, the intensity of the first X-H stretching overtone is weaker than that observed in the monomer upon hydrogen bonding [119,122,123] and the red-shift is approximately double that observed in the fundamental [3,124]. For several years, the "disappearance" of the first overtone was used as a criterion for strong hydrogen bonding [3].…”

Section: Spectroscopic Evidencementioning

confidence: 99%

Defining the hydrogen bond: An account (IUPAC Technical Report)

Arunan

Desiraju

Klein³

et al. 2011

Pure and Applied Chemistry

917

622

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Abstract:The term "hydrogen bond" has been used in the literature for nearly a century now. While its importance has been realized by physicists, chemists, biologists, and material scientists, there has been a continual debate about what this term means. This debate has intensified following some important experimental results, especially in the last decade, which questioned the basis of the traditional view on hydrogen bonding. Most important among them are the direct experimental evidence for a partial covalent nature and the observation of a blue-shift in stretching frequency following X-HؒؒؒY hydrogen bond formation (XH being the hydrogen bond donor and Y being the hydrogen bond acceptor). Considering the recent experimental and theoretical advances, we have proposed a new definition of the hydrogen bond, which emphasizes the need for evidence. A list of criteria has been provided, and these can be used as evidence for the hydrogen bond formation. This list is followed by some characteristics that are observed in typical hydrogen-bonding environments.

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“…Indeed, eighty years ago failure to observe a OH stretching overtone was correlated with the presence of an H-bond. 15 Di Paolo et al 14 explained this in terms of a balance between mechanical and electrical anhrmonicity. Suhm and co-workers' studies of a range of alcohol dimers 10,11 report fundamental-to-overtone intensity ratios in the range of 300 to 1000 for the H-bonded OH stretches, compared to about 10 for the monomeric OH.…”

Section: Introductionmentioning

confidence: 99%

Effect of hydrogen bonding on the infrared absorption intensity of OH stretch vibrations

2017

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We consider how the infrared intensity of an O-H stretch in a hydrogen bonded complex varies as the strength of the H-bond varies from weak to strong. We obtain trends for the fundamental and overtone transitions as a function of donor-acceptor distance R, which is a common measure of H-bond strength. Our calculations use a simple two-diabatic state model that permits symmetric and asymmetric bonds, i.e. where the proton affinity of the donor and acceptor are equal and unequal, respectively. The dipole moment function uses a Mecke form for the free OH dipole moment, associated with the diabatic states. The transition dipole moment is calculated using one-dimensional vibrational eigenstates associated with the H-atom transfer coordinate on the ground state adiabatic surface of our model. Over 20-fold intensity enhancements for the fundamental are found for strong H-bonds, where there are significant non-Condon effects. The isotope effect on the intensity yields a nonmonotonic H/D intensity ratio as a function of R, and is enhanced by the secondary geometric isotope effect. The first overtone intensity is found to vary non-monotonically with H-bond strength; strong enhancements are possible for strong H-bonds. Modifying the dipole moment through the Mecke parameters is found to have a stronger effect on the overtone than the fundamental. We compare our findings with those for specific molecular systems analysed through experiments and theory in earlier works. Our model results compare favourably for strong and medium strength symmetric H-bonds. However, for weak asymmetric bonds we find much smaller effects than in earlier work.

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The Hydrogen Bond between Oxygen Atoms in Some Organic Compounds

Abstract: The only serious discrepancy between these Weights are corrected to vacuum. values and the International values is with cad-Thb Atomic Weight of Protactinium Ratio KiPaF:, g. ß , g.

Cited by 84 publications

References 0 publications

Changes in H-Bonding of Cellulose During Solvent Purification Treatment (Acetonation)

Changes in H-Bonding of Cellulose During Solvent Purification Treatment (Acetonation)

Defining the hydrogen bond: An account (IUPAC Technical Report)

Effect of hydrogen bonding on the infrared absorption intensity of OH stretch vibrations

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