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Related Concept Videos

Lewis Acids and Bases02:33

Lewis Acids and Bases

43.3K
In 1923, G. N. Lewis proposed a generalized definition of acid-base behavior in which acids and bases are identified by their ability to accept or to donate a pair of electrons and form a coordinate covalent bond.
A coordinate covalent bond (or dative bond) occurs when one of the atoms in the bond provides both bonding electrons. For example, a coordinate covalent bond occurs when a water molecule combines with a hydrogen ion to form a hydronium ion. A coordinate covalent bond also results when...
43.3K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

3.7K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
3.7K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

3.2K
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.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
3.2K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

9.5K

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
9.5K
Lewis Structures of Molecular Compounds and Polyatomic Ions02:54

Lewis Structures of Molecular Compounds and Polyatomic Ions

34.3K
To draw Lewis structures for complicated molecules and molecular ions, it is helpful to follow a step-by-step procedure as outlined:
34.3K
Formation of Complex Ions03:45

Formation of Complex Ions

23.2K
A type of Lewis acid-base chemistry involves the formation of a complex ion (or a coordination complex) comprising a central atom, typically a transition metal cation, surrounded by ions or molecules called ligands. These ligands can be neutral molecules like H2O or NH3, or ions such as CN− or OH−. Often, the ligands act as Lewis bases, donating a pair of electrons to the central atom. These types of Lewis acid-base reactions are examples of a broad subdiscipline called coordination...
23.2K

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Related Experiment Video

Updated: May 28, 2025

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

9.0K

Exploring N2 activation using novel Lewis acid/base pairs: computational insight into frustrated Lewis pair

Xuban Gastearena1, Jon M Matxain1, Fernando Ruipérez2

  • 1Kimika Fakultatea, Euskal Herriko Unibertsitatea UPV/EHU and Donostia International Physics Center (DIPC), Paseo Manuel Lardizábal 4, 20018 Donostia, Euskadi, Spain.

Dalton Transactions (Cambridge, England : 2003)
|February 10, 2025
PubMed
Summary

Transition metal-free Lewis acids (LAs) capture dinitrogen (N2), while Lewis bases (LBs) activate it via a push-pull mechanism. Triptycene-based FLPs show promise for efficient N2 activation.

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Area of Science:

  • Computational Chemistry
  • Materials Science
  • Catalysis

Background:

  • Dinitrogen (N2) activation is vital for synthesizing nitrogen compounds but challenging due to its strong triple bond.
  • Current industrial N2 conversion (Haber-Bosch process) is energy-intensive, relying on transition metal catalysts.
  • Frustrated Lewis pairs (FLPs) offer a transition metal-free alternative for N2 activation.

Purpose of the Study:

  • Investigate N2 activation by transition metal-free Lewis acids (LAs) and Lewis bases (LBs) using DFT.
  • Determine the roles of LAs and LBs in N2 capture and activation.
  • Identify optimal LA-LB combinations for efficient N2 activation.

Main Methods:

  • Density Functional Theory (DFT) calculations to model N2 interactions with LAs and LBs.
  • Principal Component Analysis (PCA) to identify key factors governing LA electroaccepting power.
  • Bonding analysis to characterize LA-N2 and LB-N2 interactions.

Main Results:

  • LAs capture N2, with efficiency linked to their electroaccepting characteristics (pyramidalization, orbital occupation, electrophilicity index).
  • Triptycene-based LAs form the most stable N2 complexes, but LBs are required for full N2 triple bond activation via a 'push-pull' mechanism.
  • LB nucleophilicity enhances activation; only three LA-LB combinations exhibit FLP characteristics, with triptycene-based LAs and tris-tert-butylphosphine being most promising.

Conclusions:

  • LAs and LBs play distinct, complementary roles in transition metal-free N2 activation.
  • Triptycene-based systems are effective N2-capturing agents.
  • Optimized FLPs, particularly those involving triptycene-based LAs and tris-tert-butylphosphine, show significant potential for N2 activation.