Fluorescence excitation spectrum and solvent-assisted conformational isomerization (SACI) of jet-cooled acetaminophen

Sohn, Woon Yong; Kang, Jeong Seok; Lee, So Young; Kang, Hyuk

doi:10.1016/j.cplett.2013.07.018

Cited by 10 publications

(14 citation statements)

References 29 publications

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“…This may either be due to a better collisional cooling or due to solvent exchange mechanisms involving acetone as an intermediate binding partner. 18,30 Following the same considerations as for DMFu, methanol was deuterated to distinguish between oxygen and p coordination. The spectra are compared in Fig.…”

Section: Bfumentioning

confidence: 99%

Subtle solvation behaviour of a biofuel additive: the methanol complex with 2,5-dimethylfuran

Poblotzki

Altnöder

Suhm

2016

Phys. Chem. Chem. Phys.

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Methanol is shown to engage two nearly equivalent solvation sites in 2,5-dimethylfuran, the electron-rich π cloud and the electron-deficient oxygen site. The latter only wins by a slight margin, thanks to the methyl group undergoing secondary interactions with the ring. These secondary attractions reduce the hydrogen bond-induced OH frequency shift of the OH-O contact, whereas the π cloud allows for a combined action of both binding mechanisms in the OH-π arrangement. In total, the hydrophobic character of 2,5-dimethylfuran is well reflected in the weak pair interactions, as judged by the small solvation shifts. Methanol solvation of 2,3-benzofuran is revisited and shown to be more ambiguous than previously thought, involving competition between five- and six-ring π clouds and the oxygen site for the OH group. The six-ring π cloud is slightly preferred. FTIR spectroscopy in supersonic jets is in systematic agreement with dispersion-corrected harmonic B3LYP and also B2PLYP predictions for these competing furan docking sites. Deuteration of the OH group helps to identify the docking sites because of its attenuated zero-point energy weakening effect on localized hydrogen bonds. Extension to less methylated furans is proposed in the context of a future forecasting competition for the performance of quantum chemical methods for intermolecular interactions.

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Section: Bfumentioning

confidence: 99%

Subtle solvation behaviour of a biofuel additive: the methanol complex with 2,5-dimethylfuran

Poblotzki

Altnöder

Suhm

2016

Phys. Chem. Chem. Phys.

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“…Besides the kinematic mass effects of such heavier collision partners, they can transiently dock on the molecules of interest and bring in sufficient aggregation energy to overcome the conformational barriers. 39,40 Aer a downhill conformational transition, the released excess kinetic energy can expel the inert atom or molecule, leaving behind the molecule of interest in a lower conformational state. If the temperatures are too low (nozzle distance or stagnation pressure too large), the relaxation additives may also condense on the alkane molecules or the alkanes may self-aggregate.…”

Section: Experimental Techniquesmentioning

confidence: 99%

Stretching and folding of 2-nanometer hydrocarbon rods

Lüttschwager

Suhm

2014

Soft Matter

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Linear alkanes CnH2n+2 in vacuum isolation are finite models for an infinite polyethylene chain. Using spontaneous Raman scattering in supersonic jet expansions for n = 13-21 in different spectral ranges, we determine the minimal chain length nh for the cohesion-driven folding of the preferred extended all-trans conformation into a hairpin structure. We treat fully stretched all-trans alkanes as molecular "nanorods" and derive Young's modulus E for the stretching of an isolated single-strand polyethylene fibre by extrapolating the longitudinal acoustic mode to infinite chain length. Two key quality parameters for accurate intra- and intermolecular force fields of hydrocarbons (nh = 18 ± 1, E = 305 ± 5 GPa) are thus derived with high accuracy from experimental spectroscopy.

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“…Our previous study on acetaminophen showed that there is little difference in stability and binding energy between the cis and trans conformers of acetaminophen with solvents . Therefore, we studied only the most stable trans conformer of 3AP with halomethanes.…”

Section: Resultsmentioning

confidence: 99%

Quantum Mechanical Study on the Blue‐Shifting Hydrogen‐Bond between 3‐Aminophenol and CHX₃ (X ═ F, Cl)

Lee

Kang

2015

Bulletin Korean Chem Soc

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Intermolecular bonding between 3-aminophenol and two halomethanes, namely fluoroform and chloroform, was quantum mechanically investigated. Several low-energy structures are found, and all geometries within 1 kcal/mol show π-hydrogen bonds between the aromatic ring and the hydrogen atom of the halomethane. The C H stretching frequency of halomethane involved in the π-hydrogen bond is blue-shifted, and the amount of blue shift is the largest with the most stable isomer and decreases with decreasing stability. Binding energy, infrared intensity, and dipole moment as a function of relative stability are also reported. This study forms another example of a blue-shifting hydrogen bond, or an anti-hydrogen bond.

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Fluorescence excitation spectrum and solvent-assisted conformational isomerization (SACI) of jet-cooled acetaminophen

Cited by 10 publications

References 29 publications

Subtle solvation behaviour of a biofuel additive: the methanol complex with 2,5-dimethylfuran

Subtle solvation behaviour of a biofuel additive: the methanol complex with 2,5-dimethylfuran

Stretching and folding of 2-nanometer hydrocarbon rods

Quantum Mechanical Study on the Blue‐Shifting Hydrogen‐Bond between 3‐Aminophenol and CHX₃ (X ═ F, Cl)

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Fluorescence excitation spectrum and solvent-assisted conformational isomerization (SACI) of jet-cooled acetaminophen

Cited by 10 publications

References 29 publications

Subtle solvation behaviour of a biofuel additive: the methanol complex with 2,5-dimethylfuran

Subtle solvation behaviour of a biofuel additive: the methanol complex with 2,5-dimethylfuran

Stretching and folding of 2-nanometer hydrocarbon rods

Quantum Mechanical Study on the Blue‐Shifting Hydrogen‐Bond between 3‐Aminophenol and CHX3 (X ═ F, Cl)

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Quantum Mechanical Study on the Blue‐Shifting Hydrogen‐Bond between 3‐Aminophenol and CHX₃ (X ═ F, Cl)