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Nucleophilic Substitution Reactions02:34

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Historical perspective
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
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The word “nucleophile” has a Greek root and translates to nucleus-loving. Nucleophiles are either negatively charged or neutral species with a pair of electrons in a high-energy occupied molecular orbital (HOMO). As these species tend to donate electron pairs, nucleophiles are considered Lewis bases as well. Negatively charged species, like OH−, Cl−, or HS−, with one or several pairs of electrons, are typically nucleophiles. Similarly, neutral species such as...
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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.
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Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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Testing the Push-Pull Hypothesis: Lewis Acid Augmented N2 Activation at Iron.

Jacob B Geri1, James P Shanahan1, Nathaniel K Szymczak1

  • 1Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109, United States.

Journal of the American Chemical Society
|April 18, 2017
PubMed
Summary

Lewis acids activate iron-dinitrogen complexes, enhancing N-N bond cleavage and enabling protonation. This study explores structural and electronic changes in Fe(0)-N2 units (Fe(depe)2(N2)) with various Lewis acids.

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Area of Science:

  • Organometallic Chemistry
  • Inorganic Chemistry
  • Materials Science

Background:

  • The activation of small molecules like dinitrogen (N2) by transition metal complexes is crucial in catalysis.
  • Understanding the electronic and structural factors governing N-N bond activation is key to developing new catalytic processes.
  • Iron-nitrogen complexes offer a promising platform for N2 activation due to iron's earth-abundant nature.

Purpose of the Study:

  • To systematically investigate the impact of exogenous Lewis acids on the structural and electronic properties of an Fe(0)-N2 unit.
  • To quantify the changes in N-N bond activation, redox potential, and polarization upon Lewis acid addition.
  • To explore the feasibility of protonation at the N2 ligand under various conditions.

Main Methods:

  • Synthesis and characterization of the Fe(0)-N2 complex (Fe(depe)2(N2)).
  • Addition of various Lewis acids including neutral boranes, alkali metal cations, and an Fe(II) complex.
  • Spectroscopic analysis (e.g., IR spectroscopy to measure N-N bond stretching frequency shifts, Δ νNN).
  • Electrochemical studies to determine redox potentials.
  • Computational studies (e.g., Density Functional Theory) to rationalize observed changes.

Main Results:

  • Addition of Lewis acids significantly increases N-N bond activation, with Δ νNN up to 172 cm⁻¹.
  • Lewis acid coordination lowers the Fe(0)-N2 redox potential, indicating easier oxidation of the iron center.
  • The N-N bond becomes more polarized, facilitating further reactions.
  • Protonation of the N2 ligand is enabled at unusually anodic potentials.

Conclusions:

  • Exogenous Lewis acids effectively modulate the electronic structure of Fe(0)-N2 complexes.
  • Lewis acid interaction promotes N-N bond activation and polarization, making the dinitrogen ligand more susceptible to reactions like protonation.
  • These findings provide fundamental insights into the mechanism of N2 activation by iron complexes and suggest strategies for designing catalysts for nitrogen fixation.