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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Isomers are molecules with the same molecular formula but different structural arrangements. Isomers can be further classified into constitutional isomers and stereoisomers. Constitutional isomers differ in the connectivity of their constituent atoms. For example, 2-butanol and diethyl ether are constitutional isomers, as they have the same chemical formula, C4H10O, but differ in the connectivity of the carbon and oxygen atoms. Constitutional isomers have different physical and chemical...
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Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
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Isomerism in Complexes
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Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
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Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
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The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
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Two Structurally Characterized Conformational Isomers with Different C-P Bonds.

Sudipta Roy1,2, Kartik Chandra Mondal1,3, Subrata Kundu1

  • 1Institut für Anorganische Chemie, Universität Göttingen, Tammannstrasse 4, 37077, Göttingen, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 27, 2017
PubMed
Summary
This summary is machine-generated.

Cyclic alkyl(amino) carbenes form unique chlorophosphinidene isomers. These isomers, featuring distinct carbene-element bonds, were synthesized and characterized, revealing insights into their stability and properties.

Keywords:
cAACcarbenechlorophosphinidenedensity functional calculationsphosphaalkeneresonance forms

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Area of Science:

  • Organometallic Chemistry
  • Main Group Chemistry
  • Carbene Chemistry

Background:

  • Cyclic alkyl(amino) carbenes (cAACs) are versatile ligands in organometallic chemistry.
  • Phosphorus compounds, particularly those with low coordination numbers, exhibit unique reactivity and bonding.

Purpose of the Study:

  • To synthesize and characterize novel cyclic alkyl(amino) carbene-stabilized phosphinidene complexes.
  • To investigate the existence and structural diversity of conformational isomers in these complexes.
  • To explore the influence of the carbene ligand and the halogen/hydrogen substituent on isomer formation.

Main Methods:

  • Direct reaction of cAAC with phosphorus trichloride (PCl3).
  • Characterization using NMR spectroscopy (31P NMR) and mass spectrometry.
  • X-ray single-crystal diffraction to determine molecular structures.
  • Synthesis and characterization of bromide, iodide, and hydride analogues.
  • Theoretical calculations to support experimental findings.

Main Results:

  • Isolation and characterization of (cAAC)P-Cl, existing as two conformational isomers.
  • X-ray crystallography revealed distinct C-P bond lengths in the isomers, one resembling a P-Cl bond and the other a phosphaalkene.
  • NMR spectroscopy indicated similar equilibria for bromide, iodide, and hydride analogues.
  • Theoretical calculations provided insights into the factors governing isomer stability.

Conclusions:

  • This study presents an unprecedented example of two conformational isomers of a phosphinidene complex with differing Ccarbene-element bond characteristics.
  • The unique electronic properties of cAAC and the nature of the substituent (Cl, Br, I, H) are crucial for the observed isomerism.
  • The findings contribute to a deeper understanding of bonding and isomerism in low-coordinate phosphorus compounds.