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Related Concept Videos

Ions and Ionic Charges03:27

Ions and Ionic Charges

In ordinary chemical reactions, the nucleus — which contains the protons and neutrons of each atom and thus identifies the element — remains unchanged. Electrons, however, can be added to atoms by transfer from other atoms, lost by transfer to other atoms, or shared with other atoms. The transfer and sharing of electrons among atoms govern the chemistry of the elements. During the formation of some compounds, atoms gain or lose electrons to form electrically charged particles called ions.
The Aufbau Principle and Hund's Rule03:02

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To determine the electron configuration for any particular atom, we can build the structures in the order of atomic numbers. Beginning with hydrogen, and continuing across the periods of the periodic table, we add one proton at a time to the nucleus and one electron to the proper subshell until we have described the electron configurations of all the elements. This procedure is called the aufbau principle, from the German word aufbau (“to build up”). Each added electron occupies the subshell of...
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Electron Configuration of Multielectron Atoms

The alkali metal sodium (atomic number 11) has one more electron than the neon atom. This electron must go into the lowest-energy subshell available, the 3s orbital, giving a 1s22s22p63s1 configuration. The electrons occupying the outermost shell orbital(s) (highest value of n) are called valence electrons, and those occupying the inner shell orbitals are called core electrons. Since the core electron shells correspond to noble gas electron configurations, we can abbreviate electron...
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The elements in group 18 are noble gases (helium, neon, argon, krypton, xenon, and radon). They earned the name “noble” because they were assumed to be nonreactive since they have filled valence shells. In 1962, Dr. Neil Bartlett at the University of British Columbia proved this assumption to be false.
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Synthesis of Nine-atom Deltahedral Zintl Ions of Germanium and their Functionalization with Organic Groups
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Norbornyl cations of group 14 elements.

Thomas Müller1, Christian Bauch, Markus Ostermeier

  • 1Institut für Anorganische Chemie der Goethe Universität Frankfurt, Marie Curie-Strasse 11, D-60439 Frankfurt/Main, Federal Republic of Germany. dr.thomas.mueller@chemie.uni-frankfurt.de

Journal of the American Chemical Society
|February 20, 2003
PubMed
Summary

New norbornyl cations of group 14 elements (silicon to lead) were synthesized and characterized. These cations exhibit intramolecular interactions, with stability increasing down the group, offering insights into element bonding and reactivity.

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Published on: January 25, 2020

Area of Science:

  • Organometallic Chemistry
  • Carbocation Chemistry
  • Spectroscopy

Background:

  • Norbornyl cations are important intermediates in organic reactions.
  • Understanding the electronic properties of group 14 elements is crucial for developing new materials and catalysts.
  • Previous studies have explored silicon and germanium norbornyl cations, but heavier elements remain less investigated.

Purpose of the Study:

  • To synthesize and characterize novel norbornyl cations of group 14 elements (Si, Ge, Sn, Pb).
  • To investigate the intramolecular interactions between the positively charged element and the remote double bond.
  • To explore the stability and reactivity of these cations in different solvent environments.

Main Methods:

  • Synthesis of substituted 3-cyclopentenemethyl precursors.
  • Intramolecular addition of transient cations to the C=C double bond (pi-route).
  • Identification and characterization using Nuclear Magnetic Resonance (NMR) spectroscopy ((29)Si, (13)C, (119)Sn, (207)Pb).
  • Quantum mechanical calculations (DFT, GIAO/B3LYP) for structural, energetic, and magnetic property analysis.
  • X-ray crystallography for structural determination of lead complex.

Main Results:

  • Successfully synthesized and identified norbornyl cations of Si, Ge, Sn, and Pb (4a,e-i).
  • NMR data and coupling constants provide evidence for intramolecular interaction and charge transfer.
  • Calculations confirm bridged norbornyl cation structures with a 3+1 coordination for the element atom.
  • Stability increases from Si to Pb, with plumbanorbornyl cation showing significant stabilization.
  • Acetonitrile solvent breaks down intramolecular interaction for Si-Sn cations but forms a stable complex with the Pb cation (10i).

Conclusions:

  • Group 14 norbornyl cations can be effectively synthesized via a pi-route.
  • Intramolecular interaction between the element and the double bond is significant and element-dependent.
  • Thermodynamic stability increases down the group, while intramolecular stabilization energy decreases.
  • The reactivity towards nucleophiles like acetonitrile varies significantly, with lead exhibiting unique complexation behavior.