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Dissection and Flat-mounting of the Threespine Stickleback Branchial Skeleton

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The correct physical basis of protobranching stabilization.

Lawrence S Bartell¹

¹Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA. lbart@umich.edu

The Journal of Physical Chemistry. A

|September 28, 2012

Summary

Branched hydrocarbons gain extra stability due to "protobranching stabilization." Atomic repulsion models are challenged by quantum computations, which indicate electron correlation is the true source of this stability.

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Area of Science:

Organic Chemistry
Computational Chemistry
Quantum Chemistry

Background:

Branched hydrocarbons exhibit greater stability than their unbranched counterparts, a phenomenon termed "protobranching stabilization."
Previous models, like Gronert's atomic repulsion model, explained this stability based on steric hindrance between geminal atoms.

Purpose of the Study:

To analyze the validity of Gronert's atomic repulsion model for protobranching stabilization.
To investigate the role of electron correlation in hydrocarbon stability.

Main Methods:

Analysis of Gronert's atomic repulsion model.
Review of quantum chemical computations, including electron correlation effects.

Main Results:

Gronert's model, while intuitive, does not fully account for protobranching stabilization when electron correlation is considered.
Quantum computations by Wiberg, Bader, Grimme, Schleyer, and colleagues contradict the atomic repulsion hypothesis.

Conclusions:

The atomic repulsion model is insufficient to explain protobranching stabilization.
Bond-bond electron correlation energies are identified as the correct explanation for the enhanced stability of branched hydrocarbons.