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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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Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
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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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Published on: February 15, 2016

Bifunctional hydrogen bonds in monohydrated cycloether complexes.

Margarita M Vallejos1, Emilio L Angelina, Nélida M Peruchena

  • 1Laboratorio de Estructura Molecular y Propiedades, Area de Química Física, Departamento de Química, Facultad de Ciencias Exactas y Naturales y Agrimensura, Universidad Nacional del Nordeste, Avenida Libertad 5460, (3400) Corrientes, Argentina.

The Journal of Physical Chemistry. A
|February 9, 2010
PubMed
Summary
This summary is machine-generated.

Bifunctional hydrogen bonds in cycloethers show significant cooperative effects. These interactions mutually reinforce, stabilizing complexes more than conventional hydrogen bonds.

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Area of Science:

  • Computational Chemistry
  • Chemical Physics
  • Molecular Interactions

Background:

  • Hydrogen bonds (H-bonds) are crucial in molecular interactions.
  • Understanding cooperative effects in H-bonds is key to molecular recognition.
  • Six-membered cycloethers serve as simplified models for complex biological systems.

Purpose of the Study:

  • To investigate cooperative effects in bifunctional hydrogen bonds (H-bonds).
  • To compare bifunctional H-bonds with conventional H-bonds in model systems.
  • To analyze the stabilization arising from simultaneous polar and nonpolar interactions.

Main Methods:

  • Atoms in Molecules (AIM) theory and Natural Bond Orbitals (NBO) analysis were employed.
  • Computational studies were performed on monohydrated six-membered cycloethers (tetrahydropyrane, 1,4-dioxane, 1,3-dioxane).
  • Second-order Møller-Plesset (MP2) level theory with a 6-311++G(d,p) basis set was utilized.

Main Results:

  • Consistent indicators of H-bond strength (structural, spectroscopic, charge density, population analysis, hyperconjugation, charge transference) showed cooperative effects.
  • Bifunctional H-bonds, involving water as both proton donor and acceptor, exhibited mutual reinforcement.
  • Complexes with bifunctional H-bonds were found to be more stabilized than those with conventional H-bonds.

Conclusions:

  • Monohydrated six-membered cycloethers display significant cooperative effects in bifunctional H-bonds.
  • The dual role of water (proton donor/acceptor) leads to mutual reinforcement and enhanced stabilization.
  • Bifunctional H-bonds represent a more stable interaction compared to conventional H-bonds in these model systems.