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The Characteristics of Disulfide‐Centered Hydrogen Bonds

Xiaolong Li, Tao Lu, Daniel A. Obenchain, Jiaqi Zhang, Sven Herbers, Jens‐Uwe Grabow, Gang Feng

2020Angewandte Chemie International Edition32 citationsDOI

Abstract

Abstract The disulfide‐centered hydrogen bonds in the three different model systems of diethyl disulfide⋅⋅⋅H 2 O/H 2 CO/HCONH 2 clusters were characterized by high‐resolution Fourier transform microwave spectroscopy and quantum chemical computations. The global minimum energy structures for each cluster are experimentally observed and are characterized by one of the three different S−S⋅⋅⋅H−C/N/O disulfide‐centered hydrogen bonds and two O⋅⋅⋅H−C hydrogen bonds. Non‐covalent interaction and natural bond orbital analyses further confirm the experimental observations. The symmetry‐adapted perturbation theory (SAPT) analysis reveals that electrostatic is dominant in diethyl disulfide⋅⋅⋅H 2 O/HCONH 2 clusters being consistent with normal hydrogen bonds, whilst dispersion takes over in diethyl disulfide⋅⋅⋅H 2 CO cluster. Our study gives accurate structural parameters for the disulfide bond involved non‐covalent clusters providing important benchmarking data for the theoretical evaluation of more complex systems.

Topics & Concepts

Hydrogen bondCovalent bondCluster (spacecraft)ChemistryDisulfide bondCrystallographySpectroscopyMoleculeMolybdenum disulfideComputational chemistryChemical physicsMaterials scienceOrganic chemistryPhysicsBiochemistryMetallurgyQuantum mechanicsProgramming languageComputer scienceMolecular Spectroscopy and StructureAdvanced Chemical Physics StudiesAtmospheric Ozone and Climate
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