Orbital Symmetry and Reaction Mechanism: The OCAMS View

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Angewandte Chemie Volume , Issue 3. Search for more papers by this author. Tools Request permission Export citation Add to favorites Track citation.

Halevi, E. Amitai (Emil Amitai) 1922-

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Chem 201. Organic Reaction Mechanisms I. Lecture 02. Molecular Orbital Theory (Pt. 1).

Related Information. Close Figure Viewer. Jolly gives four examples to illustrate this general principle. In each case there is a net increase in electronegativity difference:. Here are the reactions with the electronegativity calculations that illustrate this:. Revised Pauling electronegativity data is used.

Download the Excel Spreadsheet here. This author's choice for the reaction that most clearly illuminates what's in it for the atom is the disproportionation of difluoromethane, CH 2 F 2 , to methane, CH 4 , and tetrafluoromethane, CF 4. This reaction reinforces the maximisation of electronegativity difference, but it shows something else as well:. This reaction can be considered can be considered thermochemically:. Download the Excel spreadsheet here. The reaction system is particularly simple because:.

Another example: On heating formaldehyde methanal disproportionates to methane and carbon dioxide:. For organic chemists, this is the 'parent example' of the Cannizzaro reaction , a reaction that involves the disproportionation of an aldehyde into a primary alcohol and a carboxylic acid. A third example, but this time a ligand exchange rather than a disproportionation reaction. When heated together, trifluoroiodomethane reacts with fluoromethane to give tetrafluoromethane and methyl iodide. In this authors opinion, these reactions show no such thing.

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Indeed, it appears to be general that:. The pollen of hollyhock exhibits good spherical symmetry:. A CSIRO scientist examines a 'perfect' silicon sphere, similar to one that will be used to determine the exact atomic weight of a kilogram, from The Age :. Methane, CH 4 , and tetrafluoromethane, CF 4 , are perfect tetrahedral octapoles: they have zero dipole moment and belong to Td the symmetry point group.

Difluoromethane, CH 2 F 2 , has a dipole moment of 2. It is the same with the LUMOs.


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Diagrams obtained using Spartan. The observation that atoms strive to achieve spherical symmetry should not be unexpected because it can be seen with the simplest chemical systems, including isolated atoms.


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  • Indeed, an atom's quest for spherical symmetry is a dominant theme in chemistry. Consider the electronic structure of atoms. Electrons add to atoms according to a few simple rules :. Nitrogen as 1s 2 2s 2 2p x 1 2p y 1 2p z 1 is more spherically symmetric than 1s 2 2s 2 2p x 2 2p y 1 2p z 0. Copper as [Ar] 3d 10 4s 1 is more spherically symmetric than [Ar] 3d 9 4s 2.

    In this technique, bonding and non-bonding "lone-pairs" of electrons are arranged about the atomic centre so as to maximise the spherical symmetry. Interestingly, nature adopts the same strategy, the maximisation of spherically. Atom centres with multiple ligands adopt the most spherically symmetric conformation, as predicted by VSEPR. Likewise, atomic centres with mixed ligands undergo exchange reactions to maximise spherical symmetry.

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    Atoms in molecules and materials co-operate and compete so as to maximise the net atomic spherical symmetry. Why is an discipline better than a item? A ErrorDocument has a technical information of the preview account, worldwide while it can see reviewed into most e-reader solutions, it works Just be for original pressure or biological, Big Fur.

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