Unprecedented observation and characterization of sulfur-centred bifurcated hydrogen bonds

Owing to the small electronegativity of the sulfur atom, it is commonly supposed that at most one weak H-bond can be formed between a sulfur atom and an H-bond donor. In this paper, an unprecedented 2 : 1 binding species generated from two molecules of phenol and a molecule of thioether was observed...

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Published in:Physical chemistry chemical physics : PCCP 2021-12, Vol.23 (46), p.26519-26523
Main Authors: Ma, Xiantao, Zhu, Yingying, Yu, Jing, Zhao, Geng, Duanmu, Jiaxin, Yuan, Yiyun, Chang, Xue-Ping, Xu, Dongli, Zhou, Qiuju
Format: Article
Language:English
Subjects:
Bifurcations
Bonding strength
Density functional theory
Electronegativity
Fourier transforms
Hydrogen bonds
NMR
Nuclear magnetic resonance
Organic chemistry
Sulfur
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Summary:Owing to the small electronegativity of the sulfur atom, it is commonly supposed that at most one weak H-bond can be formed between a sulfur atom and an H-bond donor. In this paper, an unprecedented 2 : 1 binding species generated from two molecules of phenol and a molecule of thioether was observed and characterized by various nuclear magnetic resonance (NMR) techniques, Fourier transform-infrared (FT-IR) techniques and density functional theory (DFT) calculations, revealing the formation of sulfur-centred O-H S H-O bifurcated H-bonds. This work may provide a simple and efficient method for the quantitative analysis of weak H-bonds between small organic molecules. It is observed that the sulfur atom can unprecedentedly serve as a good acceptor to form the O-H S H-O bifurcated H-bond.
ISSN:1463-9076
1463-9084
DOI:10.1039/d1cp04601b