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Stereoisomerism02:52

Stereoisomerism

14.6K
Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
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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Complexation Equilibria: The Chelate Effect01:19

Complexation Equilibria: The Chelate Effect

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In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...
1.6K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.3K
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...
4.3K
¹H NMR Chemical Shift Equivalence: Homotopic and Heterotopic Protons01:03

¹H NMR Chemical Shift Equivalence: Homotopic and Heterotopic Protons

4.8K
Protons in identical electronic environments within a molecule are chemically equivalent and have the same chemical shift. The replacement test is a useful tool to identify chemical equivalence and predict NMR spectra. A substituent replaces each of the protons being examined and the resulting molecules are compared. If the same molecule is obtained, the protons are equivalent or homotopic. Replacement of any hydrogens in ethane by chlorine yields chloroethane because all six protons are...
4.8K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.7K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.7K
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

15.1K
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.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
15.1K

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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
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Exploring the Transphobia Effect on Heteroleptic NHC Cycloplatinated Complexes.

Sara Fuertes1, Andrés J Chueca1, Violeta Sicilia2

  • 1Departamento de Química Inorgánica, Facultad de Ciencias, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza , Pedro Cerbuna 12, 50009 Zaragoza, Spain.

Inorganic Chemistry
|October 9, 2015
PubMed
Summary

This study details an improved synthesis of N-heterocyclic carbene (NHC) ligands and their use in creating novel cycloplatinated compounds. The research explores ligand transphobia and trans influence in platinum complexes.

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Synthetic Chemistry

Background:

  • N-heterocyclic carbenes (NHCs) are versatile ligands in organometallic chemistry.
  • Cycloplatinated compounds exhibit diverse applications, including catalysis and materials science.
  • Understanding ligand effects on metal complex geometry is crucial for designing new functional molecules.

Purpose of the Study:

  • To develop an improved synthesis of a specific NHC precursor, 1-(4-cyanophenyl)-1H-imidazol.
  • To synthesize and characterize novel cycloplatinated NHC complexes.
  • To investigate the geometric preferences and electronic properties of these platinum complexes based on ligand substitution.

Main Methods:

  • Improved synthesis of 1-(4-cyanophenyl)-1H-imidazol and its imidazolium salt.
  • Step-by-step synthesis of cycloplatinated intermediate and final complexes.
  • Isolation and characterization of platinum complexes using spectroscopic techniques.
  • Analysis of complex geometries using transphobia (T) values and theoretical calculations.

Main Results:

  • Successful synthesis of a cycloplatinated NHC precursor and various heteroleptic platinum complexes.
  • Isolation of intermediate complex [PtCl(η(3)-2-Me-C3H4) (HC^C*-κC*)] (3).
  • Observation of cis- and trans-isomers for some complexes, with trans isomers predominating in others.
  • Correlation of complex geometry with ligand transphobia and theoretical calculations.

Conclusions:

  • The developed synthetic route provides efficient access to NHC-based cycloplatinated compounds.
  • Ligand properties, particularly transphobia, significantly influence the geometry of the resulting platinum complexes.
  • The study offers insights into the trans influence of Pt-C bonds in these systems.