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The Molecular Structure of Cyclobutane

Dunitz, J. D. and Schomaker, Verner (1952) The Molecular Structure of Cyclobutane. Journal of Chemical Physics, 20 (11). pp. 1703-1707. ISSN 0021-9606. https://resolver.caltech.edu/CaltechAUTHORS:20161017-111309523

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Abstract

The cyclobutane molecule has been found by electron diffraction to have the following bond distances and bond angles: C–C, 1.568±0.02A; C–H, 1.098±0.04A; ∠HCH, 114±8°. On the average the ring is nonplanar, with dihedral angle 20° (+10°, −20°), but the equilibrium symmetry may be either D_(2d) (puckered ring) or D_(4h) (planar ring with low rigidity leading to large amplitude of out‐of‐plane bending). This point is discussed in connection with earlier spectroscopic work. The long bond distances found in four‐membered rings are contrasted against the short distances in three‐membered rings, and the strain energies, bond distances, and HCH angles of cycloalkanes are discussed in terms of modern valence concepts. It is suggested that the potential energy arising from a repulsion of the nonbonded carbon atoms may contribute significantly to the apparently anomalously high strain energy of cyclobutane. The repulsive force associated with such a potential is shown to account satisfactorily for the long C–C distances.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1063/1.1700271DOIArticle
http://scitation.aip.org/content/aip/journal/jcp/20/11/10.1063/1.1700271PublisherArticle
Additional Information:© 1952 American Institute of Physics. (Received May 9, 1952)
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Gates and Crellin Laboratories of Chemistry1691
Issue or Number:11
Record Number:CaltechAUTHORS:20161017-111309523
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20161017-111309523
Official Citation:The Molecular Structure of Cyclobutane Dunitz, J. D. and Schomaker, Verner, The Journal of Chemical Physics, 20, 1703-1707 (1952), DOI:http://dx.doi.org/10.1063/1.1700271
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:71169
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:17 Oct 2016 20:44
Last Modified:03 Oct 2019 16:04

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