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Related Concept Videos

Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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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.
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Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
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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.
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

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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,...
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Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

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Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Synthesis of Nine-atom Deltahedral Zintl Ions of Germanium and their Functionalization with Organic Groups
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The seven-membered nickelacycle [NiBr=(o-CH=C(CF3)C6H4CH2PPh2-kappa2C,P)(PPh(CH2Ph)2)].

Alison J Edwards1, Eric Wenger

  • 1Research School of Chemistry, Australian National University, ACT 0200, Australia. alison.edwards@anu.edu.au

Acta Crystallographica. Section C, Crystal Structure Communications
|April 5, 2002
PubMed
Summary

The crystal structure of a novel phosphanickelacycle compound was determined. This organometallic complex features a unique trifluoromethyl group and provides insights into nickel-carbon bond chemistry.

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Crystallography

Background:

  • Phosphanickelacycles are important intermediates in organometallic synthesis.
  • Understanding the structural properties of these complexes is crucial for predicting reactivity.
  • The insertion of alkynes into metal-carbon bonds is a fundamental transformation.

Purpose of the Study:

  • To determine the crystal and molecular structure of a novel phosphanickelacycle.
  • To characterize the geometric parameters of the nickel-ligand bonds.
  • To elucidate the regioselectivity of alkyne insertion into a nickel-carbon bond.

Main Methods:

  • X-ray crystallography was employed to determine the crystal structure.
  • Single-crystal X-ray diffraction data were collected and analyzed.
  • Geometric parameters such as bond lengths and angles were precisely measured.

Main Results:

  • The crystal structure of 3-bromo-3-(dibenzylphenylphosphonio)-2,2-diphenyl-5-trifluoromethyl-1H-benzo[e][1,2]phosphanickelepine was elucidated.
  • Key bond lengths (Ni-Br, Ni-P, Ni-C) and trans angles (P-Ni-P, Br-Ni-C) were reported.
  • The compound was obtained as the major regioisomer from the insertion of HCCCF(3) into a phosphanickelacycle.

Conclusions:

  • The determined structure provides detailed geometric information about this organometallic complex.
  • The findings contribute to the understanding of alkyne insertion reactions in nickel chemistry.
  • This study offers a structural basis for further investigations into related phosphanickelacycle systems.