Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Structure of Amines

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...

VSEPR Theory and the Effect of Lone Pairs

VSEPR Theory and the Effect of Lone Pairs

Effect of Lone Pairs of Electrons on Molecule Geometry

Structures of Carboxylic Acid Derivatives

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

Five-Membered Heterocyclic Aromatic Compounds: Overview

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.

Radicals: Electronic Structure and Geometry

Radicals: Electronic Structure and Geometry

This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Double Möbius Aromaticity in the Oxo-Platinum Complex.

Inorganic chemistry·2026

Same author

Selective Oxidation of Benzyl Alcohol in Water With Cobalt-Exchanged Zeolite-NaY Catalyst.

ChemPlusChem·2026

Same author

Rhabdomyolysis-Induced Resistant Hypercalcemia During the Recovery Phase of Acute Kidney Injury.

Cureus·2026

Same author

Electronic Structure of All-Metal Neutral M<sub>4</sub> (M = Al, Ga, In) Rings: Aromaticity and Spin-Avoided σ-σ Diradical Character.

The journal of physical chemistry. A·2026

Same author

Formulation of a Modified <i>Aloe vera</i>-Based Emulgel for Sustained Release of Methotrexate: Integrated Experimental and Theoretical Approaches.

ACS omega·2026

Same author

Ligand-induced release of HNO/NO<sup>-</sup> from a cobalt(II)-nitrosyl complex.

Chemical communications (Cambridge, England)·2026

Search research articles

Related Experiment Video

Updated: Jun 16, 2026

On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes

On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes

Published on: August 5, 2016

Planar Pentacoordinate Nitrogen with Activated N─N Bond.

Amit Das¹, Palash J Thakuria¹, Ankur K Guha¹

¹Advanced Computational Chemistry Centre, Cotton University, Panbazar, Guwahati, Assam, India.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry

|June 14, 2026

Summary

This summary is machine-generated.

Researchers discovered a novel planar pentacoordinate nitrogen atom in the Li4H3N2- cluster. This global minimum features an activated N=N double bond, challenging traditional main group chemistry principles.

Keywords:

activated N2 bond global minimum planar pentacoordinate nitrogen theoretical

More Related Videos

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents

Published on: May 28, 2014

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Related Experiment Videos

Last Updated: Jun 16, 2026

On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes

On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes

Published on: August 5, 2016

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents

Published on: May 28, 2014

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Area of Science:

Computational chemistry
Main group chemistry
Quantum chemistry

Background:

Traditional understanding of main group compounds is being challenged by computational discoveries.
Investigating unusual bonding and structural motifs in main group chemistry is crucial.

Purpose of the Study:

To present a novel planar pentacoordinate nitrogen atom as the global minimum (GM) for the Li4H3N2- cluster.
To analyze the bonding characteristics and stability of this unique cluster structure.

Main Methods:

Detailed quantum chemical calculations were employed.
Electronic structure studies utilized adaptive natural density partitioning (AdNDP), atoms in molecules (AIM), and extended transition state coupled with natural orbital for chemical valence (ETS-NOCV).

Main Results:

A planar pentacoordinate nitrogen atom was identified as the global minimum for the Li4H3N2- cluster.
The cluster features an activated N=N double bond within an N2 unit.
The global minimum is stabilized by electrostatic and multicentre bonding interactions.
Strong electrostatic nature of N-Li interaction was confirmed.

Conclusions:

The discovery of a planar pentacoordinate nitrogen atom in Li4H3N2- expands the known structural possibilities for main group compounds.
This finding highlights the importance of computational methods in uncovering novel chemical structures and bonding paradigms.
The unique bonding in this cluster, particularly the N-Li interaction, offers new insights into main group chemistry.