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Hydrogen Bonding and Dominant Conformation of Hydrated Sugar Analogue Complexes: Tetrahydrofurfuryl Alcohol as the Example

Abstract

Water molecule, which serves as the hydrogen bond donor and acceptor, has been found to influence the conformational landscape of gas-phase phenyl-β-D-glucopyranoside. Herein, tetrahydrofurfuryl alcohol (THFA), a sugar-like molecule without chromophore (e.g. Phenyl-substitution), was taken as the model sugar molecule to explore the behaviour of water molecule on the conformational landscape of the pentose such as the deoxyribose. We used mass selected infrared-vacuum ultraviolet (IR-VUV) (118 nm) spectroscopy to investigate the hydrated THFA neutral in a supersonic jet and its complex cation in a supersonic jet. High level density functional theory (DFT) calculations were performed to ascertain the experimental results. The results revealed that the water molecule tends to insert into the twisted conformer at a position, where two stronger intermolecular hydrogen bonds were formed by breaking the weak intramolecular interactions. We found that the twisted conformer of hydrated THFA complex neutral is more stable than the envelope one while the latter is more stable for the THFA molecule. However, the conformational landscape of hydrated THFA complex cation has not been changed significantly by microsolvation of water molecule. The results indicated that the dominant structural landscape of hydrated cationic complex is the twisted configuration with a trans-hydroxymethyl group. The finding provides valuable insights into the microsolvation of gas-phase sugar molecules.

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Publication details

The article was received on 25 Nov 2017, accepted on 11 Feb 2018 and first published on 13 Feb 2018


Article type: Paper
DOI: 10.1039/C7CP07935D
Citation: Phys. Chem. Chem. Phys., 2018, Accepted Manuscript
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    Hydrogen Bonding and Dominant Conformation of Hydrated Sugar Analogue Complexes: Tetrahydrofurfuryl Alcohol as the Example

    S. Jin, Y. Hu, P. Wang, H. Zhan, Q. Lu, F. Liu and L. Sheng, Phys. Chem. Chem. Phys., 2018, Accepted Manuscript , DOI: 10.1039/C7CP07935D

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