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Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

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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.
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Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

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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.
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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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Structure of Amines01:19

Structure of Amines

3.1K
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...
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Structure and Physical Properties of Alkynes02:37

Structure and Physical Properties of Alkynes

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Introduction:
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The...
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Chirality at Nitrogen, Phosphorus, and Sulfur02:30

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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...
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Determination of Inorganic Arsenic in a Wide Range of Food Matrices using Hydride Generation - Atomic Absorption Spectrometry.
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HC3As, the simplest arsadiyne.

Arun-Libertsen Lawzer1, Thomas Custer1, Jean-Claude Guillemin2

  • 1Institute of Physical Chemistry, Polish Academy of Sciences, ul. Marcina Kasprzaka 44/52, 01-224, Warsaw, Poland. alawzer@ichf.edu.pl.

Dalton Transactions (Cambridge, England : 2003)
|December 16, 2025
PubMed
Summary

1-Arsabutadiyne (HC3As) is synthesized via photolysis of propynylarsine in solid argon. Its infrared spectra and molecular properties resemble those of HC3P but differ greatly from HC3N.

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Area of Science:

  • Chemistry
  • Spectroscopy
  • Quantum Chemistry

Background:

  • Understanding the properties of small carbon-chain molecules containing heteroatoms is crucial.
  • Previous studies have focused on related compounds like HC3N and HC3P.

Purpose of the Study:

  • To synthesize and characterize 1-arsabutadiyne (HC3As).
  • To compare the molecular properties of HC3As with those of HC3P and HC3N.

Main Methods:

  • Photolysis of propynylarsine isolated in solid argon at cryogenic temperatures.
  • Infrared absorption spectroscopy to analyze the synthesized molecule.
  • Computational methods to predict molecular parameters.

Main Results:

  • Efficient production of 1-arsabutadiyne (HC3As) was achieved through photolysis.
  • Observed infrared absorption spectra of HC3As showed significant similarities to HC3P.
  • Predicted molecular parameters for HC3As also closely matched those of HC3P.
  • Large differences were noted when comparing HC3As to HC3N.

Conclusions:

  • 1-Arsabutadiyne (HC3As) is a stable molecule that can be synthesized under specific laboratory conditions.
  • The chemical and physical properties of HC3As are more akin to its phosphorus analog (HC3P) than its nitrogen analog (HC3N).
  • This study provides valuable data for understanding the trends in properties across the series of propynylidenes (HC3X).