Vibrational relaxation and frequency shifts of proton acceptors in hydrogen-bonded systems. Benzonitrile in solutions

Abramczyk, Halina; Reimschüssel, W.

doi:10.1016/0301-0104(85)85007-2

Cited by 17 publications

(16 citation statements)

References 40 publications

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“…π-π stacking between the aromatic groups of 5CB and Tyr, hydrogen-bonding between C=O and NH groups of the dipeptide backbone and van der Waals interactions) are present in these systems. 76–78 In summary, our experimental results, when combined with prior FTIR studies of hydrogen bonding between benzonitrile and phenol, 71,73,74 support our conclusion that hydrogen-bonding between the –OH group of Tyr and 5CB plays a central role in ordering the 5CB. 71,73,74 …”

Section: Resultssupporting

confidence: 83%

Enantiomeric Interactions between Liquid Crystals and Organized Monolayers of Tyrosine-Containing Dipeptides

Bai

Abbott

2011

J. Am. Chem. Soc.

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We have examined the orientational ordering of nematic liquid crystals (LCs) supported on organized monolayers of dipeptides with the goal of understanding how peptide-based interfaces encode intermolecular interactions that are amplified into supramolecular ordering. By characterizing the orientations of nematic LCs (4-cyano-4′-pentylbiphenyl (5CB) and TL205 (a mixture of mesogens containing cyclohexane-fluorinated biphenyls and fluorinated terphenyls)) on monolayers of either L-cysteine-L-tyrosine, L-cysteine-L-phenylalanine or L-cysteine-L-phosphotyrosine formed on crystallographically textured films of gold, we conclude that patterns of hydrogen bonds generated by the organized monolayers of dipeptides are transduced via macroscopic orientational ordering of the LCs. This conclusion is supported by the observation that the ordering exhibited by the achiral LCs is specific to the enantiomers used to form the dipeptide-based monolayers. The dominate role of the –OH group of tyrosine in dictating the patterns of hydrogen bonds that orient the LCs was also evidenced by the effects of phosphorylation of the tyrosine on the ordering of the LCs. Overall, these results reveal that crystallographic texturing of gold films can direct the formation of monolayers of dipeptides with long-range order, thus unmasking the influence of hydrogen bonding, chirality and phosphorylation on the macroscopic orientational ordering of LCs supported on these surfaces. These results suggest new approaches based on supramolecular assembly for reporting the chemical functionality and stereochemistry of synthetic and biological peptide-based molecules displayed at surfaces.

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Section: Resultssupporting

confidence: 83%

Enantiomeric Interactions between Liquid Crystals and Organized Monolayers of Tyrosine-Containing Dipeptides

Bai

Abbott

2011

J. Am. Chem. Soc.

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“…Such a band splitting observed in the clusters may be quite important to investigate the dynamics of CN of BN in solution, in view of the fact that the CN Raman band of BN is widely broadened in solution. [37][38][39][40][41] Though several models are suggested to explain the broadening, the present result indicates that the splitting of CN due to cluster formation is mainly responsible for the broadening in solution. Figure 9 shows the FDSR spectra for 6a , 1 , and 12 vibrations.…”

Section: Cn Stretching Vibration ( Cn )mentioning

confidence: 46%

Mode dependent intracluster vibrational energy redistribution rate in size-selected benzonitrile–(CHCl3)n=1–3 clusters

Yamamoto

Ebata

Mikami

2001

The Journal of Chemical Physics

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The rate constants of intracluster vibrational energy redistribution (IVR) of benzonitrile–(CHCl3)1 for the 121 (1000 cm−1), 11 (760 cm−1), and 6a1 (460 cm−1) levels have been measured by time-resolved stimulated Raman-UV double resonance spectroscopy. It was found that the observed rate constants are independent of the energies but strongly dependent on the vibrational modes. In order to find a relationship between the structure and the IVR rate, structures of benzonitrile–(CHCl3)n=1–3 have been determined based on the results of the Raman spectra and the high resolution S1–S0 electronic spectra for the size-selected clusters, and ab initio MO calculations. The Raman spectra were observed for both CHCl3 and benzonitrile sites. It was found that the CH stretching vibration of the CHCl3 moiety showed a higher frequency shift in the clusters, whose magnitude depends on the binding site to benzonitrile. For the benzonitrile moiety, the Raman spectra of CH stretch (ν2), CN stretch (νCN), ring breathing (ν12 and ν1), and CCC in-plane bending (ν6a) vibrations were investigated. From those results, it was concluded that the clusters have the form such that the CH hydrogen of the first CHCl3 is hydrogen-bonded to the N end of the CN group, while second and third CHCl3 are hydrogen-bonded to the phenyl ring. The observed mode dependence of the IVR rate constants will be discussed based on the cluster structure and the vibrational motion.

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“…This is known as a p-type H-bond, because the p electrons of the triple bond accept the H-bond. [17] According to the DFT calculations, the C N stretching frequency of the R800-(H 2 O) 6 cluster is 2331.3 cm À1 , which is 5.4 cm À1 lower than that of free R800, and 15.2 cm À1 lower than that of the R800-(H 2 O) 12 cluster. Experimentally, the red shift of the CN frequency from bulk water to the air/water interface is 22 cm À1 , which is close to the theoretically calculated difference between the R800-(H 2 O) 12 and R800-(H 2 O) 6 clusters.…”

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confidence: 97%

χ⁽⁴⁾ Raman Spectroscopy for Buried Water Interfaces

Yamaguchi¹,

Tahara²

2007

Angew Chem Int Ed

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π‐Type H‐bonds that are not found in bulk liquid phases, where σ‐type H‐bonds prevail, were detected for the dye rhodamine 800 at air/water and fused silica/water interfaces (see picture) by interface‐selective fourth‐order nonlinear (χ(4)) Raman spectroscopy in the frequency domain. This new method allows vibrational spectra of organic solutes at liquid interfaces to be obtained in the whole fingerprint region (200–2800 cm−1).

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Vibrational relaxation and frequency shifts of proton acceptors in hydrogen-bonded systems. Benzonitrile in solutions

Cited by 17 publications

References 40 publications

Enantiomeric Interactions between Liquid Crystals and Organized Monolayers of Tyrosine-Containing Dipeptides

Enantiomeric Interactions between Liquid Crystals and Organized Monolayers of Tyrosine-Containing Dipeptides

Mode dependent intracluster vibrational energy redistribution rate in size-selected benzonitrile–(CHCl3)n=1–3 clusters

χ⁽⁴⁾ Raman Spectroscopy for Buried Water Interfaces

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Vibrational relaxation and frequency shifts of proton acceptors in hydrogen-bonded systems. Benzonitrile in solutions

Cited by 17 publications

References 40 publications

Enantiomeric Interactions between Liquid Crystals and Organized Monolayers of Tyrosine-Containing Dipeptides

Enantiomeric Interactions between Liquid Crystals and Organized Monolayers of Tyrosine-Containing Dipeptides

Mode dependent intracluster vibrational energy redistribution rate in size-selected benzonitrile–(CHCl3)n=1–3 clusters

χ(4) Raman Spectroscopy for Buried Water Interfaces

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χ⁽⁴⁾ Raman Spectroscopy for Buried Water Interfaces