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Related Concept Videos

Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

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As depicted in the figure below, the unsymmetrical ketones can form two possible enolates:  less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are  more stable. But the energy required to form kinetic enolates is less.
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

14.6K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
14.6K
Electrophiles02:28

Electrophiles

11.0K
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...
11.0K
Nucleophiles02:30

Nucleophiles

13.8K
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...
13.8K
Reactivity of Enolate Ions01:23

Reactivity of Enolate Ions

2.7K
Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, leading to a resonance-stabilized enolate ion where one of the contributing structures is an oxyanion, which imparts additional stability. Therefore, the proton on the α carbon is more acidic in nature than that of other sp3-hybridized C–H bonds but less acidic than those in O–H bonds where the negative charge in the conjugate...
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Protein Film Infrared Electrochemistry Demonstrated for Study of H2 Oxidation by a [NiFe] Hydrogenase
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Unveiling the Protonation Kinetics-Dependent Selectivity in Nitrogen Electroreduction: Achieving 75.05 % Selectivity.

Yang Liu1,2, Lingling Wang1,2, Lin Chen3

  • 1Center for Integrated Nanostructure Physics, Institute for Basic Science (IBS), Sungkyunkwan University, Suwon, 16419, Republic of Korea.

Angewandte Chemie (International Ed. in English)
|October 26, 2022
PubMed
Summary

This study reveals that nitrogen reduction reaction (NRR) selectivity hinges on initial nitrogen protonation kinetics. Tailored iron polysulfide catalysts, like FeCuSx, achieve high ammonia selectivity by optimizing this crucial step.

Keywords:
Adjustable Protonation KineticsElectronic ModulationNitrogen ElectroreductionOperando Electrochemical Impedance Spectroscopy SimulationsProtonation-Selectivity Relation

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Area of Science:

  • Electrochemistry and Catalysis
  • Materials Science
  • Inorganic Chemistry

Background:

  • Achieving high selectivity in the nitrogen reduction reaction (NRR) to ammonia (NH3) is crucial for sustainable fertilizer production.
  • The precise mechanisms governing NRR selectivity, particularly the role of nitrogen protonation, remain poorly understood, especially in alkaline media.

Purpose of the Study:

  • To elucidate the theoretical dependence of NRR selectivity on the initial nitrogen protonation step.
  • To investigate how proton availability, adsorption-desorption, and intermediate *NNH formation influence selectivity.
  • To develop novel catalysts with tunable protonation kinetics for enhanced ammonia production.

Main Methods:

  • Theoretical profiling of NRR selectivity based on first protonation kinetics.
  • Synthesis of FeMSx catalysts by incorporating electronic metal modulators (M=Co, Ni, Cu, Zn) into a nitrogenase-mimicking FeSx model.
  • In situ FT-IR and Raman spectroscopy, along with operando electrochemical impedance spectroscopy, to track key intermediates and reaction kinetics.

Main Results:

  • A strong correlation between protonation kinetics and NRR selectivity was established, following a log-linear Bradley curve.
  • FeCuSx catalysts demonstrated tunable protonation kinetics.
  • A record-high NH3 selectivity of 75.05% was achieved with FeCuSx at -0.1 V (vs. RHE) in 0.1 M KOH.

Conclusions:

  • The initial nitrogen protonation step is a critical determinant of NRR selectivity in alkaline electrolytes.
  • Tailoring protonation kinetics through catalyst design, exemplified by FeCuSx, offers a promising strategy for efficient ammonia synthesis.
  • The findings provide fundamental insights into NRR mechanisms and guide the development of next-generation electrocatalysts.