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strain energy

The excess energy due to steric strain of a molecular entity or transition state structure, i.e. distortions relative to a reference (real or hypothetical) 'strainless' structure with the standard bond lengths, bond angles and dihedral angles. The strain energy components involve the following destabilizing terms: non-bonded repulsions, bond-angle distortions, bond stretch or compression, rotation around or twisting of double bonds, and electrostatic strain. In general, the contributions of these components are inseparable and interdependent. A quantitative assessment of strain and strain energies can be made by taking the difference between the heat of formation of the substance under consideration and that of a hypothetical strain-free model. Several approaches to the assessment of strain energies have been developed based on the use of energies of isodesmic and homodesmotic reactions and on the so-called 'strainless increments', i.e. heats of formation of certain groups (CH3, CH2, CH, C etc).
PAC, 1999, 71, 1919 (Glossary of terms used in theoretical organic chemistry) on page 1964
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IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.ST07108.
Original PDF version: http://www.iupac.org/goldbook/ST07108.pdf. The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
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