Anti-Hydrogen Bond in the Benzene Dimer and Other Carbon Proton Donor Complexes

Hobza, Pavel; Špirko, V.; Selzle, H. L.; Schlag, E. W.

doi:10.1021/jp973374w

Cited by 347 publications

(280 citation statements)

References 11 publications

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“…This elongation behavior contrasts markedly with the contractions that occur in the CH⅐⅐O H-bonds of all amino acids as well as F 2 HCH. This seemingly opposite behavior, observed in a number of CH⅐⅐O bonds (46,(62)(63)(64)(65)(66)(67), has nevertheless been demonstrated to be consistent with the characterization of the CH⅐⅐O interaction as a true H-bond (54). There is no clear pattern concerning the magnitude of this contraction.…”

Section: Resultsmentioning

confidence: 77%

Strength of the CαH··O Hydrogen Bond of Amino Acid Residues

Scheiner

Kar

2001

Journal of Biological Chemistry

285

239

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Although the peptide C␣ H group has historically not been thought to form hydrogen bonds within proteins, ab initio quantum calculations show it to be a potent proton donor. Its binding energy to a water molecule lies in the range between 1.9 and 2.5 kcal/mol for nonpolar and polar amino acids; the hydrogen bond (H-bond) involving the charged lysine residue is even stronger than a conventional OH⅐⅐O interaction. The preferred H-bond lengths are quite uniform, about 3.32 Å. Formation of each interaction results in a downfield shift of the bridging hydrogen's chemical shift and a blue shift in the C ␣ H stretching frequency, potential diagnostics of the presence of such an H-bond within a protein.

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Section: Resultsmentioning

confidence: 77%

Strength of the CαH··O Hydrogen Bond of Amino Acid Residues

Scheiner

Kar

2001

Journal of Biological Chemistry

285

239

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“…This is, however, not completely true and even the first complex for which the improper H-bonding was theoretically predicted, benzene dimer in the T-shaped structure 189 , belongs to this family. It is thus evident that still other mechanisms must exist.…”

Section: Fig 17mentioning

confidence: 97%

The World of Non-Covalent Interactions: 2006

Hobza¹,

Zahradník²,

Müller‐Dethlefs³

2006

Collect. Czech. Chem. Commun.

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244

235

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The review focusses on the fundamental importance of non-covalent interactions in nature by illustrating specific examples from chemistry, physics and the biosciences. Laser spectroscopic methods and both ab initio and molecular modelling procedures used for the study of non-covalent interactions in molecular clusters are briefly outlined. The role of structure and geometry, stabilization energy, potential and free energy surfaces for molecular clusters is extensively discussed in the light of the most advanced ab initio computational results for the CCSD(T) method, extrapolated to the CBS limit. The most important types of non-covalent complexes are classified and several small and medium size non-covalent systems, including H-bonded and improper H-bonded complexes, nucleic acid base pairs, and peptides and proteins are discussed with some detail. Finally, we evaluate the interpretation of experimental results in comparison with state of the art theoretical models: this is illustrated for phenol...Ar, the benzene dimer and nucleic acid base pairs. A review with 270 references.

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“…19 -22 Another point of interest is the behavior of the C-H donor oscillator. Ab initio calculations consistently predict a shortening of the C-H bond, with the corresponding blue shift of the C-H mode, upon C-HÐ Ð ÐO hydrogen bonding (which has been referred to as an anti-hydrogen bond 23 or improper blue-shifting hydrogen bond 24 owing to this unconventional behavior). The experimental evidence for such effects is still scarce and all the new data on the subject are expected to give a contribution to the rationalization of the phenomenon.…”

Section: Introductionmentioning

confidence: 98%

C—H···O hydrogen bonds in liquid cyclohexanone revealed by the νCO splitting and the νC–H blue shift

Vaz¹,

Ribeiro‐Claro²

2003

J Raman Spectroscopy

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The presence of C -H· · ·O hydrogen bonds in liquid cyclohexanone is concluded from a combined theoretical and vibrational spectroscopic study. The two bands present in the nC O region, clearly observed in the Raman spectrum, are assigned to 'free' and 'bonded' carbonyl groups from their temperature-dependent and solvent-dependent relative intensities. In addition, a band exhibiting the same intensity dependence in the nC-H region is tentatively assigned to the blue-shifted nC-H· · ·(O) mode.

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Anti-Hydrogen Bond in the Benzene Dimer and Other Carbon Proton Donor Complexes

Cited by 347 publications

References 11 publications

Strength of the CαH··O Hydrogen Bond of Amino Acid Residues

Strength of the CαH··O Hydrogen Bond of Amino Acid Residues

The World of Non-Covalent Interactions: 2006

C—H···O hydrogen bonds in liquid cyclohexanone revealed by the νCO splitting and the νC–H blue shift

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