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Strain is present in a molecular entity or transition structure if the energy is enhanced because of unfavourable bond lengths, bond angles or dihedral angles ('torsional strain') relative to a standard. It is quantitatively defined as the standard enthalpy of a structure relative to a strainless structure (real or hypothetical) made up from the same atoms with the same types of bonding. (The enthalpy of formation of cyclopropane is 53.6 kJ mol −1, whereas the enthalpy of formation based on three 'normal' methylene groups, from acyclic models, is −62 kJ mol −1. On this basis cyclopropane is destabilized by ca. 115 kJ mol −1 of strain energy.)
PAC, 1994, 66, 1077 (Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)) on page 1168
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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.S06037.
Original PDF version: http://www.iupac.org/goldbook/S06037.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 The PDF version is out of date and is provided for reference purposes only.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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