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Hydrogen Bonds01:04

Hydrogen Bonds

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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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Hydrogen Bonds00:26

Hydrogen Bonds

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Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
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Valence Bond Theory02:45

Valence Bond Theory

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Overview of Valence Bond Theory
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Hybridization of Atomic Orbitals II

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sp3d and sp3d 2 Hybridization
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Intermolecular Forces03:13

Intermolecular Forces

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Atoms and molecules interact through bonds (or forces): intramolecular and intermolecular. The forces are electrostatic as they arise from interactions (attractive or repulsive) between charged species (permanent, partial, or temporary charges) and exist with varying strengths between ions, polar, nonpolar, and neutral molecules. The different types of intermolecular forces are ion–dipole, dipole–dipole, hydrogen bonds, and dispersion; among these, dipole–dipole, hydrogen...
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Electrophiles02:28

Electrophiles

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This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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CF2H, a Hydrogen Bond Donor.

Chanan D Sessler1, Martin Rahm2, Sabine Becker1

  • 1Department of Chemistry, Massachusetts Institute of Technology , 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.

Journal of the American Chemical Society
|June 4, 2017
PubMed
Summary
This summary is machine-generated.

The CF2H group acts as an unusual hydrogen bond donor, mimicking the OH group. This study confirms the bioisosterism of OH and CF2H groups, highlighting unique hydrogen bonding roles in molecular interactions.

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Area of Science:

  • Chemical Physics
  • Structural Chemistry
  • Supramolecular Chemistry

Background:

  • The hydroxyl (OH) group is fundamental in biological systems and materials, primarily through hydrogen bonding.
  • Exploring functional group surrogates is crucial for designing novel molecules with tailored properties.
  • The difluoromethyl (CF2H) group presents an intriguing alternative due to its electronic and steric characteristics.

Purpose of the Study:

  • To investigate the hydrogen bonding capabilities of the difluoromethyl (CF2H) group.
  • To establish the bioisosterism between the hydroxyl (OH) and difluoromethyl (CF2H) groups.
  • To elucidate the influence of CF2H-H···O hydrogen bonds on intermolecular interactions and molecular conformations.

Main Methods:

  • Crystallographic analysis to determine structural features.
  • Spectroscopic techniques (e.g., NMR, IR) to probe hydrogen bonding.
  • Computational chemistry (e.g., DFT calculations) to model interactions and energetics.

Main Results:

  • The CF2H group demonstrably functions as a hydrogen bond donor.
  • Experimental and theoretical data confirm the bioisosteric relationship between OH and CF2H groups.
  • CF2H-H···O hydrogen bonds exhibit distinct characteristics compared to conventional OH···O bonds, influencing molecular assembly and conformation.

Conclusions:

  • The CF2H group is a viable and unique hydrogen bond donor, serving as a bioisostere for the OH group.
  • CF2H hydrogen bonding significantly impacts intermolecular forces and conformational landscapes.
  • Understanding these interactions opens new avenues in medicinal chemistry and materials science.