The Structure and Thermal Stability of 1,2-Dimethoxycarbonyl-3,3-dimethylcyclopropene

Sangdon Han; Tina Arrowood; Victor G. Young; Steven R. Kass

doi:10.1023/A:1022039426948

The Structure and Thermal Stability of 1,2-Dimethoxycarbonyl-3,3-dimethylcyclopropene

Sangdon Han, Tina Arrowood, Victor G. Young, Steven R. Kass

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

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Abstract

The X-ray crystal structure of 1,2-dimethoxycarbonyl-3,3-dimethylcyclopropene (1) is reported and the geometry is contrasted to that of cyclopropene (2) and 3,3-dimethylcyclopropene (3). Ab initio and density functional theory calculations were carried out in order to examine the conformational preference of the ester groups (i.e., s-cis vs. s-trans) and to probe the thermal stability of 1 via a model compound, 1-methoxycarbonyl-3-methylcyclopropene. Experimental activation parameters for the unimolecular isomerization were measured and compared to an analogous dibenzoylcyclopropene derivative.

Original language	English (US)
Pages (from-to)	349-354
Number of pages	6
Journal	Structural Chemistry
Volume	10
Issue number	5
DOIs	https://doi.org/10.1023/A:1022039426948
State	Published - 1999

Bibliographical note

Funding Information:
Support from the National Science Foundation, the donors of the Petroleum Research Foundation, as administered by the American Chemical Society, the University of Minnesota Supercomputing Institute, and the University of Minnesota-IBM Shared University Research Program are gratefully acknowledged.

Keywords

Cyclopropene derivatives
Molecular orbital calculations
Unimolecular isomerization
X-ray analysis

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title = "The Structure and Thermal Stability of 1,2-Dimethoxycarbonyl-3,3-dimethylcyclopropene",

abstract = "The X-ray crystal structure of 1,2-dimethoxycarbonyl-3,3-dimethylcyclopropene (1) is reported and the geometry is contrasted to that of cyclopropene (2) and 3,3-dimethylcyclopropene (3). Ab initio and density functional theory calculations were carried out in order to examine the conformational preference of the ester groups (i.e., s-cis vs. s-trans) and to probe the thermal stability of 1 via a model compound, 1-methoxycarbonyl-3-methylcyclopropene. Experimental activation parameters for the unimolecular isomerization were measured and compared to an analogous dibenzoylcyclopropene derivative.",

keywords = "Cyclopropene derivatives, Molecular orbital calculations, Unimolecular isomerization, X-ray analysis",

author = "Sangdon Han and Tina Arrowood and Young, {Victor G.} and Kass, {Steven R.}",

note = "Funding Information: Support from the National Science Foundation, the donors of the Petroleum Research Foundation, as administered by the American Chemical Society, the University of Minnesota Supercomputing Institute, and the University of Minnesota-IBM Shared University Research Program are gratefully acknowledged.",

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T1 - The Structure and Thermal Stability of 1,2-Dimethoxycarbonyl-3,3-dimethylcyclopropene

AU - Han, Sangdon

AU - Arrowood, Tina

AU - Young, Victor G.

AU - Kass, Steven R.

N1 - Funding Information: Support from the National Science Foundation, the donors of the Petroleum Research Foundation, as administered by the American Chemical Society, the University of Minnesota Supercomputing Institute, and the University of Minnesota-IBM Shared University Research Program are gratefully acknowledged.

PY - 1999

Y1 - 1999

N2 - The X-ray crystal structure of 1,2-dimethoxycarbonyl-3,3-dimethylcyclopropene (1) is reported and the geometry is contrasted to that of cyclopropene (2) and 3,3-dimethylcyclopropene (3). Ab initio and density functional theory calculations were carried out in order to examine the conformational preference of the ester groups (i.e., s-cis vs. s-trans) and to probe the thermal stability of 1 via a model compound, 1-methoxycarbonyl-3-methylcyclopropene. Experimental activation parameters for the unimolecular isomerization were measured and compared to an analogous dibenzoylcyclopropene derivative.

AB - The X-ray crystal structure of 1,2-dimethoxycarbonyl-3,3-dimethylcyclopropene (1) is reported and the geometry is contrasted to that of cyclopropene (2) and 3,3-dimethylcyclopropene (3). Ab initio and density functional theory calculations were carried out in order to examine the conformational preference of the ester groups (i.e., s-cis vs. s-trans) and to probe the thermal stability of 1 via a model compound, 1-methoxycarbonyl-3-methylcyclopropene. Experimental activation parameters for the unimolecular isomerization were measured and compared to an analogous dibenzoylcyclopropene derivative.

KW - Cyclopropene derivatives

KW - Molecular orbital calculations

KW - Unimolecular isomerization

KW - X-ray analysis

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The Structure and Thermal Stability of 1,2-Dimethoxycarbonyl-3,3-dimethylcyclopropene

Abstract

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Keywords

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