Application of the Variable Oxygen Probe to Determine the π-Electron Donor Ability of the Alkyne Group
Benjamin L. Harris A and Jonathan M. White A B
+ Author Affiliations
- Author Affiliations
A School of Chemistry and the BIO-21 Institute, The University of Melbourne, Parkville, Vic. 3010, Australia.
B Corresponding author. Email: whitejm@unimelb.edu.au
Australian Journal of Chemistry 67(12) 1866-1870 https://doi.org/10.1071/CH14395
Submitted: 18 June 2014 Accepted: 31 July 2014 Published: 18 September 2014
Abstract
Eight ester and ether derivatives of propargyl alcohol with varying electron demand were structurally characterised using low temperature X-ray crystallography, these were combined with seven derivatives obtained from the Cambridge Structural Database. Variable oxygen probe analysis of these derivatives provided evidence that the ethynyl substituent is a relatively weak π-electron donor, and is a slightly less effective donor than the C–C bond of an ethyl substituent.
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