The DOI matches its Crossref record; 15 of the 15 references it cites were found in a registry or an index.
Strain Energy of Small Ring Hydrocarbons. Influence of C−H Bond Dissociation Energies
Abstract
Ab initio calculations at the G2, G3, and CBS-Q levels of theory have been applied to the question of the origin of ring strain in a series of unsaturated hydrocarbons. In addition to the angular ring strain germane to all three-membered ring hydrocarbons, a general trend is in evidence that suggests that the increased ring strain (SE) of unsaturated small ring alkenes may be attributed in part to their relatively weak allylic C-H bonds. The high strain energy of cyclopropene (54.1 kcal/ mol) is attributed largely to angular strain. The anomalously low SE of cyclobutene relative to cyclobutane (DeltaSE = 4 kcal/mol) is a consequence of normal C-H bond dissociation energies for cyclobutane (100.6 kcal/mol) and very strong vinyl C-H bonds (111.9 kcal/mol) and a relatively strong pi-bond energy (63.5 kcal/mol) for cyclobutene. The greater SE of methylenecyclopropane (39.5 kcal/ mol), relative to methylcyclopropane (29.8 kcal/mol), can be attributed to the strong ring C-H bonds of methylcyclopropane (110.5 kcal/mol) and relatively weak allylic C-H bonds (99.3 kcal/mol) of methylenecyclopropane. The increased SE of 1-methylcyclopropene relative to isomeric methylenecyclopropane is ascribed to its weak ring C-H bonds and to angular strain. The relative thermodynamic stability of a series of small ring alkenes is determined by a measure of their hydrogenation enthalpies. Independent confirmation of the SEs of a series of substituted cyclopropenes is provided by their dimerization/combination with cyclopropane to form a six-membered ring reference compound.
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Herner, A., & Lin, Q. (2016) · Topics in Current Chemistry · doi:10.1007/s41061-015-0002-2 · Cited by 339
Cyclobutadiene: the antiaromatic paradigm?
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Metadata
- Authors
- Bach, R. D., & Dmitrenko, O.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-03-13
- Volume
- 126
- Issue
- 13
- Pages
- 4444-4452
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1997363111
- Cited by
- 302
- References
- 15
- FWCI
- 6.96
- Type
- journal article
- Language
- en
- Open access
- closed
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