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Related Concept Videos

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

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.
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
Other Nuclides: 31P, 19F, 15N NMR01:16

Other Nuclides: 31P, 19F, 15N NMR

Many organic, inorganic, and biological molecules contain spin-half nuclei such as nitrogen-15, fluorine-19, and phosphorus-31. As a result, NMR studies of these nuclei have found extensive applications in chemical and biological research.
While fluorine-19 and phosphorous-31 have high natural abundances (100%) and positive gyromagnetic ratios, nitrogen-15 has a low natural abundance and a negative gyromagnetic ratio. However, nitrogen-15 is still preferred over nitrogen-14 (which has a high...
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...

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Related Experiment Video

Updated: Jul 9, 2026

Nitrogen Compound Characterization in Fuels by Multidimensional Gas Chromatography
08:22

Nitrogen Compound Characterization in Fuels by Multidimensional Gas Chromatography

Published on: May 15, 2020

Nitrogen-rich B(C6F5)2-derived polycyclic molecules.

Huan Liu1,2, Shaoying Ju2, Beili Tang2

  • 1Faculty of Chemical Engineering and Energy Technology, Shanghai Institute of Technology, Shanghai 201418, China. xhzhang@sit.edu.cn.

Chemical Communications (Cambridge, England)
|July 8, 2026
PubMed
Summary
This summary is machine-generated.

New N-rich polycyclic compounds derived from boron bis(pentafluorophenyl) (B(C6F5)2) were synthesized. One compound shows strong fluorescence, indicating its potential as a novel dye scaffold.

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

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

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Last Updated: Jul 9, 2026

Nitrogen Compound Characterization in Fuels by Multidimensional Gas Chromatography
08:22

Nitrogen Compound Characterization in Fuels by Multidimensional Gas Chromatography

Published on: May 15, 2020

On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes
07:49

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

Published on: August 5, 2016

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Area of Science:

  • Synthetic inorganic chemistry
  • Materials science
  • Computational chemistry

Background:

  • Boron-containing heterocycles are of interest due to their unique electronic properties.
  • N-rich polycyclic compounds offer diverse structural motifs and potential applications.

Purpose of the Study:

  • To synthesize and characterize novel N-rich polycyclic species incorporating the B(C6F5)2 moiety.
  • To investigate the electronic properties and potential applications of these new compounds.

Main Methods:

  • Synthesis of B(C6F5)2-derived N-rich polycyclic compounds.
  • Characterization using NMR and IR spectroscopy, and single-crystal X-ray diffraction.
  • Density Functional Theory (DFT) calculations to study electronic structures.

Main Results:

  • Successful synthesis and full characterization of a series of novel compounds.
  • DFT calculations showed that the B(C6F5)2 group narrows the Highest Occupied Molecular Orbital-Lowest Unoccupied Molecular Orbital (HOMO-LUMO) gap.
  • The N,B-fused bistriazaborole derivative (compound 8) displayed strong fluorescence with a significant Stokes shift.

Conclusions:

  • The synthesized compounds represent a new class of N-rich polycyclic boron species.
  • The B(C6F5)2 moiety effectively modulates the electronic properties, reducing the HOMO-LUMO gap.
  • Compound 8 shows promise as a fluorescent dye scaffold for potential applications in materials science.