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Hydrogen Bonds01:04

Hydrogen Bonds

15.4K
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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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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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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Valence Bond Theory02:45

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Overview of Valence Bond Theory
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ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

7.0K
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
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Hydrogen Bonding: Regulator for Nucleophilic Fluorination.

Shengzong Liang1, Gerald B Hammond1, Bo Xu2

  • 1Department of Chemistry, University of Louisville, Louisville, Kentucky, 40292, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 24, 2017
PubMed
Summary

Hydrogen bonding enhances nucleophilic fluorination reactions by controlling the reactivity of fluorine sources. New reagents like HF/DMPU offer advantages over traditional methods for various fluorination applications.

Keywords:
alkali metalsfluoridesfluorinationhydrogen bondingnucleophiles

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Area of Science:

  • Organic Chemistry
  • Fluorination Chemistry
  • Hydrogen Bonding

Background:

  • Nucleophilic fluorination is crucial in organic synthesis.
  • Alkali-metal fluorides are common but have limitations like strong basicity and uncontrollable nucleophilicity.
  • Hydrogen bonding offers a strategy to modulate these properties.

Purpose of the Study:

  • To summarize recent advances in nucleophilic fluorination regulated by hydrogen bonding.
  • To discuss the advantages of novel hydrogen-bonding-controlled fluorine nucleophiles.

Main Methods:

  • Review of literature on nucleophilic fluorination techniques.
  • Discussion of alkali-metal fluorides and hydrogen-bonding strategies.
  • Comparison of HF/DMPU with conventional reagents like HF/pyridine and HF/Et3N.

Main Results:

  • Hydrogen bonding effectively fine-tunes the nucleophilicity and basicity of fluorine sources.
  • HF/DMPU demonstrates superior performance in certain fluorination reactions due to DMPU's high hydrogen bond basicity.
  • HF/DMPU has been successfully applied in fluorination of alkynes, fluoro-Prins reaction, and aziridines.

Conclusions:

  • Hydrogen bonding is a powerful tool for controlling nucleophilic fluorination.
  • HF/DMPU represents a significant advancement in nucleophilic fluorination reagents.
  • These advances expand the scope and efficiency of incorporating fluorine into organic molecules.