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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
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Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...
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Color in Coordination Complexes
When atoms or molecules absorb light at the proper frequency, their electrons are excited to higher-energy orbitals. For many main group atoms and molecules, the absorbed photons are in the ultraviolet range of the electromagnetic spectrum, which cannot be detected by the human eye. For coordination compounds, the energy difference between the d orbitals often allows photons in the visible range to be absorbed and emitted, which is seen as colors by the human...
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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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Isomerism in Complexes
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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Ambireactive (R3 P)2 BH2 Groups Facilitating Temperature-Switchable Bond Activation by an Iron Complex.

Lisa Vondung1, Lars E Sattler1, Robert Langer1

  • 1Department of Chemistry, Philipps-Universität Marburg, Hans-Meerwein-Str. 4, 35032, Marburg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 10, 2017
PubMed
Summary

This study introduces an iron pincer complex with temperature-switchable reactivity. It demonstrates reversible B-H activation and C-H activation, enabling novel H/D exchange catalysis.

Keywords:
C−H activationboroncooperative effectshydridesiron

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Iron Complexes

Background:

  • Pincer complexes are crucial in catalysis due to their unique coordination environment.
  • Controlling reactivity through external stimuli like temperature is a key challenge in catalyst design.
  • Hemi-labile ligands offer tunable electronic and steric properties for catalytic applications.

Purpose of the Study:

  • To investigate the temperature-dependent reactivity of a novel iron pincer complex.
  • To elucidate the mechanisms behind switchable B-H and C-H activation pathways.
  • To develop an iron-catalyzed protocol for H/D exchange in organic solvents.

Main Methods:

  • Synthesis and characterization of the iron pincer complex featuring a (R3P)2BH2 ligand.
  • Variable-temperature studies to observe reactivity changes.
  • Mechanistic investigations including kinetic and spectroscopic analyses.
  • Development and testing of the H/D exchange protocol.

Main Results:

  • The iron complex exhibits reversible B-H activation and P-B bond cleavage at room temperature.
  • Below 4°C, intra- and intermolecular C-H activation become dominant reaction pathways.
  • Ligand lability and exothermic sigma-bond formation drive the switchable bond activation.
  • An efficient iron-catalyzed H/D exchange of organic solvents was achieved without oxidants.

Conclusions:

  • The hemi-labile (R3P)2BH2 ligand enables temperature-switchable reactivity in iron pincer complexes.
  • Understanding these mechanisms allows for precise control over catalytic pathways.
  • This work provides a new method for H/D exchange catalysis using earth-abundant iron.