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Kinetic and equilibrium study of gas-phase interconversions of 1,3,6-cyclooctatriene, 1,3,5-cyclooctatriene and bicyclo[4.2.0]octa-2,4-diene

✍ Scribed by John M. Greathead; S. Walter Orchard

Publisher: John Wiley and Sons
Year: 1983
Tongue: English
Weight: 589 KB
Volume: 15
Category: Article
ISSN: 0538-8066
DOI: 10.1002/kin.550151011

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✦ Synopsis

Abstract

The gas‐phase equilibrium and rate constants for the isomerizations of 1,3,6‐cyclooctatriene (136COT) to 1,3,5‐cyclooctatriene (135COT) [reaction (1)] and bicyclo[4.2.0]octa‐2,4‐diene (BCO) to 135COT [reaction (‐2)] have been measured between 390 and 490 K and between 330 and 475 K, respectively. The rate constant of reaction (1) obeys the Arrhenius equation
The corresponding equilibrium constant is given by the van′t Hoff equation
The strain energy of the 136COT ring is calculated to be 31.7 kJ/mol, based on the known value of 37.2 kJ/mol for 135COT, and Δ__H__(298 K) for gaseous 136COT is 196.3 kJ/mol. The rate constant of reaction (‐2) obeys the Arrhenius equation
The equilibrium constant for 135COT ⇆ BCO fits the van′t Hoff equation
The strain energy of the BCO skeleton is calculated to be 108.3 kJ/mol, and Δ__H__(298 K) for gaseous BCO is 183.3 kJ/mol.

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