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Stable pentacoordinate carbocations: structure and bonding.

Israel Fernández1, Einar Uggerud, Gernot Frenking

  • 1Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse, 35032 Marburg, Germany. israel@quim.ucm.es

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 31, 2007
PubMed
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Elements more electropositive than carbon form stable pentacoordinate carbon structures. These molecules feature a planar CH3 group bonded to two electropositive moieties, forming a three-center, two-electron bond.

Area of Science:

  • Quantum Chemistry
  • Computational Chemistry
  • Organic Chemistry

Background:

  • Understanding chemical bonding in unusual molecular geometries is crucial.
  • Pentacoordinate carbon species are rare and challenging to characterize.
  • The analogy with SN2 transition states provides a framework for investigation.

Purpose of the Study:

  • To identify elements that form stable pentacoordinate carbon structures.
  • To analyze the bonding characteristics of these novel molecules.
  • To elucidate the electronic structure of HnE--CH3--EHn+ species.

Main Methods:

  • Theoretical calculations were employed.
  • Energy Decomposition Analysis (EDA) was used to study interaction energy.
  • Electronic structure of the molecules was analyzed.

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Main Results:

  • Only elements more electropositive than carbon (Group 13, 14, and Be) form stable HnE--CH3--EHn+ structures.
  • These structures exhibit a planar CH3 group symmetrically bonded to two EHn moieties.
  • The bonding involves a three-center, two-electron sigma bond between the CH3 group and the two EHn groups.

Conclusions:

  • Stable pentacoordinate carbon molecules are formed by elements with high electropositivity relative to carbon.
  • The bonding in these molecules is characterized by a delocalized three-center, two-electron bond.
  • These findings expand the understanding of chemical bonding and molecular structures.