Nuclear quantum and H/D isotope effects on intramolecular hydrogen bond in curcumin

Udagawa, Taro; Yabushita, Hiromitsu; Tanaka, Hikaru; Kuwahata, Kazuaki; Tachikawa, Masanori

doi:10.1039/d3cp01821k

Cited by 3 publications

(3 citation statements)

References 21 publications

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“…Fast, reversible dislocation of the H atom along the O–O axis, however, should not completely scramble the OH stretch dipole orientation. Small fluctuations of the H/D atoms around the equilibrium position should likewise result in partial anisotropy decay. , While rapid fluctuations of the H/D atom positions certainly contribute to the early time orientational dynamics, they should not contribute to the longer time scales nor result in complete decay of the anisotropy.…”

Section: Resultsmentioning

confidence: 99%

Investigating Intramolecular H Atom Transfer Dynamics in β-Diketones with Ultrafast Infrared Spectroscopies and Theoretical Modeling

Dean,

Winkler,

Boyer

et al. 2023

J. Phys. Chem. A

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The vibrational signatures and ultrafast dynamics of the intramolecular H-bond in a series of β-diketones are investigated with 2D IR spectroscopy and computational modeling. The chosen β-diketones exhibit a range of H atom donor–acceptor distances and asymmetry along the H atom transfer coordinate that tunes the intramolecular H-bond strength. The species with the strongest H-bonds are calculated to have very soft H atom potentials, resulting in highly red-shifted OH stretch fundamental frequencies and dislocation of the H atom upon vibrational excitation. These soft potentials lead to significant coupling to the other normal mode coordinates and give rise to the very broad vibrational signatures observed experimentally. The 2D IR spectra in both the OH and OD stretch regions of the light and deuterated isotopologues reveal broadened and long-lived ground-state bleach signatures of the vibrationally hot molecules. Polarization-sensitive transient absorption measurements in the OH and OD stretch regions reveal notable isotopic differences in orientational dynamics. Orientational relaxation was measured to occur on ∼600 fs and ∼2 ps time scales for the light and deuterated isotopologues, respectively. The orientational dynamics are interpreted in terms of activated H/D atom transfer events driven by collective intramolecular structural rearrangements.

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Section: Resultsmentioning

confidence: 99%

Investigating Intramolecular H Atom Transfer Dynamics in β-Diketones with Ultrafast Infrared Spectroscopies and Theoretical Modeling

Dean,

Winkler,

Boyer

et al. 2023

J. Phys. Chem. A

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“…For example, several groups and we have reported that NQEs of hydrogen nuclei enhance the hydrogen bond strength and facilitate proton transfer reactions. 19–24 Furthermore, we have also demonstrated that considering the NQEs is indispensable for the analysis of the H/D isotope effects. 24…”

Section: Introductionmentioning

confidence: 90%

“…19–24 Furthermore, we have also demonstrated that considering the NQEs is indispensable for the analysis of the H/D isotope effects. 24…”

Section: Introductionmentioning

confidence: 90%

Nuclear quantum and H/D isotope effects on aromaticity: path integral molecular dynamics study

Tanaka,

Kuwahata,

Tachikawa

et al. 2024

Phys. Chem. Chem. Phys.

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Nuclear quantum effects on the intramolecular hydrogen bonds in biuret and biguanide

Nishikawa,

Tanaka,

Kuwahata

et al. 2024

Phys. Chem. Chem. Phys.

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Nuclear quantum and H/D isotope effects on intramolecular hydrogen bond in curcumin

Abstract: Low-barrier hydrogen bond in curcumin and hemicurcuminoids are studied. Path integral molecular dynamics simulations reveal that the correlation between the proton migration and the reorganization of the π-delocalized structure is not so strong.

Cited by 3 publications

References 21 publications

Investigating Intramolecular H Atom Transfer Dynamics in β-Diketones with Ultrafast Infrared Spectroscopies and Theoretical Modeling

Investigating Intramolecular H Atom Transfer Dynamics in β-Diketones with Ultrafast Infrared Spectroscopies and Theoretical Modeling

Nuclear quantum and H/D isotope effects on aromaticity: path integral molecular dynamics study

Nuclear quantum effects on the intramolecular hydrogen bonds in biuret and biguanide

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