Stereochemistry of Cyclobutane and Heterocyclic Analogs

Moriarty, Robert M.

doi:10.1002/9780470147177.ch4

Cited by 59 publications

(3 citation statements)

References 245 publications

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“…Consequently, we have begun to review the possible impact of the new formulas on the kinds of study that have been made on cyclobutanes, and on studies of further kinds. The 150‐page survey of cyclobutanes and heterocyclic analogues by Moriarty 29 provides a definitive introduction to the field and a framework for discussing the developments over the 30 years since it appeared. These include the determination of the puckering or planarity of many 4‐atom ring compounds from experimental data.…”

Section: Puckering In Cyclobutanesmentioning

confidence: 99%

Modular chemical geometry and symbolic calculation

Barnett¹,

Capitani²

2005

Int J of Quantum Chemistry

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ABSTRACT:We discuss (a) the construction of formulas for the puckering of 4 and 5 atom rings from simple geometrical principles; (b) the application of these formulas to the study of cyclobutanes and heterocyclic analogues; (c) the way the derivations are represented (i.e., the style facilitates symbolic calculations for many more chemical topics; (d) interfacing the Gaussian package and Mathematica; and (e) some representations of molecular properties in Mathematica and algorithmic operations on these.

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Section: Puckering In Cyclobutanesmentioning

confidence: 99%

Modular chemical geometry and symbolic calculation

Barnett¹,

Capitani²

2005

Int J of Quantum Chemistry

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“…In particular, I was asked by the Guest Editor of this thematic issue of the International Journal of Quantum Chemistry to provide the detailed geometrical analysis of the dipole moment calculation that was summarized in Ref. [1] and incorporated by Moriarty in his survey of the chemistry of cyclobutanes and their heterocyclic analogues [3]. (The values for the angle of pucker for the 1,3-dichlorocyclobutanes reported in Ref.…”

mentioning

confidence: 99%

“…(The values for the angle of pucker for the 1,3-dichlorocyclobutanes reported in Ref. [3], page 307, were transposed. The cis-isomer should be 32°, and the trans-isomer should be 37°.)…”

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confidence: 99%

Geometry of 1,3‐dihalocyclobutanes by dipole moment analysis

Lampman

Aumiller

2005

Int J of Quantum Chemistry

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ABSTRACT:The dipole moments of cis and trans-1,3-dichloro-, 1,3-dibromo-, and 1,3-diiodocyclobutanes were obtained. The deviation from planarity (angle of puckering) was calculated from the dipole moments. In all cases, the compounds were found to be non-planar (puckered). Although the angle strain increases slightly for a non-planar ring, the decrease in torsional strain becomes more important. For the cisseries, it was found that the angle of puckering was largest for the 1,3-diiodocyclobutane. For the trans-series the angle of puckering was the least for the 1,3-diiodocyclobutane. trans-1,3-Dibromo-1,3-dimethylcyclobutane has the least amount of puckering of all the compounds studied.

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Multistep Conformational Interconversion Mechanisms

Dale

1976

Topics in Stereochemistry

107

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Stereochemistry of Cyclobutane and Heterocyclic Analogs

Cited by 59 publications

References 245 publications

Modular chemical geometry and symbolic calculation

Modular chemical geometry and symbolic calculation

Geometry of 1,3‐dihalocyclobutanes by dipole moment analysis

Multistep Conformational Interconversion Mechanisms

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