Journal of the American Chemical Society, volume 126, issue 13, pages 4444-4452
Strain Energy of Small Ring Hydrocarbons. Influence of C−H Bond Dissociation Energies
1
Contribution from the Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716
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Publication type: Journal Article
Publication date: 2004-03-13
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
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.
Top-30
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25
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Citations by publishers
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10
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40
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60
70
80
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Wiley
77 publications, 33.48%
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American Chemical Society (ACS)
71 publications, 30.87%
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Elsevier
29 publications, 12.61%
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Royal Society of Chemistry (RSC)
29 publications, 12.61%
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Springer Nature
9 publications, 3.91%
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Thieme
3 publications, 1.3%
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Taylor & Francis
2 publications, 0.87%
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Beilstein-Institut
1 publication, 0.43%
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American Institute of Physics (AIP)
1 publication, 0.43%
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Bentham Science
1 publication, 0.43%
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World Scientific
1 publication, 0.43%
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Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 0.43%
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IOP Publishing
1 publication, 0.43%
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American Association for the Advancement of Science (AAAS)
1 publication, 0.43%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 0.43%
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10
20
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Bach R., Dmitrenko O. Strain Energy of Small Ring Hydrocarbons. Influence of C−H Bond Dissociation Energies // Journal of the American Chemical Society. 2004. Vol. 126. No. 13. pp. 4444-4452.
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Bach R., Dmitrenko O. Strain Energy of Small Ring Hydrocarbons. Influence of C−H Bond Dissociation Energies // Journal of the American Chemical Society. 2004. Vol. 126. No. 13. pp. 4444-4452.
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TY - JOUR
DO - 10.1021/ja036309a
UR - https://doi.org/10.1021/ja036309a
TI - Strain Energy of Small Ring Hydrocarbons. Influence of C−H Bond Dissociation Energies
T2 - Journal of the American Chemical Society
AU - Dmitrenko, Olga
AU - Bach, Robert
PY - 2004
DA - 2004/03/13 00:00:00
PB - American Chemical Society (ACS)
SP - 4444-4452
IS - 13
VL - 126
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2004_Bach,
author = {Olga Dmitrenko and Robert Bach},
title = {Strain Energy of Small Ring Hydrocarbons. Influence of C−H Bond Dissociation Energies},
journal = {Journal of the American Chemical Society},
year = {2004},
volume = {126},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/ja036309a},
number = {13},
pages = {4444--4452},
doi = {10.1021/ja036309a}
}
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Bach, Robert, and Olga Dmitrenko. “Strain Energy of Small Ring Hydrocarbons. Influence of C−H Bond Dissociation Energies.” Journal of the American Chemical Society, vol. 126, no. 13, Mar. 2004, pp. 4444-4452. https://doi.org/10.1021/ja036309a.