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Related Concept Videos

Hydrogen Bonds01:04

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A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
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Coupling interactions are strongest between NMR-active nuclei bonded to each other, where spin information can be transmitted directly through the pair of bonding electrons. While nuclei polarize their electrons to the opposite spins, the bonding electron pair has opposite spins. Configurations with antiparallel nuclear spins are expected to be lower in energy. When coupling makes antiparallel states more favorable, J is considered to have a positive value. The one-bond coupling constant, 1J,...
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The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
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The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
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Noncovalent attractions are associations within and between molecules that influence the shape and structural stability of complexes. These interactions differ from covalent bonding in that they do not involve sharing of electrons.
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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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C-H⋯S hydrogen bonding interactions.

Hazel A Fargher1, Tobias J Sherbow1, Michael M Haley1

  • 1Department of Chemistry and Biochemistry, Materials Science Institute, Knight Campus for Accelerating Scientific Impact, and Institute of Molecular Biology, University of Oregon, Eugene, Oregon, 97403-1253, USA. haley@uoregon.edu.

Chemical Society Reviews
|February 1, 2022
PubMed
Summary
This summary is machine-generated.

Short C-H⋯S contacts are a crucial, often overlooked, stabilizing interaction in molecules. This study confirms C-H⋯S bonds are a type of hydrogen bonding, vital for understanding molecular interactions.

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Area of Science:

  • Supramolecular Chemistry
  • Chemical Crystallography
  • Biomolecular Interactions

Background:

  • Short C-H⋯S contacts are prevalent in small molecules and biomolecular systems.
  • These interactions are frequently overlooked yet contribute significantly to molecular stability.
  • Many C-H⋯S contacts fulfill the criteria for hydrogen bonding.

Purpose of the Study:

  • To establish the generality and significance of C-H⋯S hydrogen bonding.
  • To compare C-H⋯S interactions with traditional hydrogen bonds.
  • To investigate the influence of coordination number and metal bonding on C-H⋯S geometry.

Main Methods:

  • Analysis of structural data from the Cambridge Structural Database (CSD).
  • Examination of literature examples featuring C-H⋯S contacts.
  • Comparative analysis with established hydrogen bond donors and acceptors.

Main Results:

  • C-H⋯S contacts are confirmed to be a valid and important class of hydrogen bonds.
  • The study highlights the widespread nature of these interactions across various systems.
  • Geometric preferences for C-H⋯S interactions are influenced by coordination and metal bonding.

Conclusions:

  • C-H⋯S bonds meet the definition of hydrogen bonding.
  • These interactions are a generally applicable stabilizing force in molecular structures.
  • Provides a framework for identifying C-H⋯S hydrogen bonds in diverse chemical and biological systems.