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Ethoxyethyl 3-octylamino-2-cyanoacrylate and related compounds in which the amino group was replaced by N-CH 3 , S, O and CH 2  were synthesized and their activity as inhibitors of the Hill reaction in isolated pea chloroplasts determined. All compounds showed moderate to high activity but there was no obvious correlation between activity and the electronic character of the ester carbonyl group. The stereochemistry of the various inhibitor molecules was deduced from the PMR spectra and the possible influence of stereochemistry on Hill inhibitory activity discussed. Replacement of the olefinic proton in the 2-cyanoacrylates with a β-alkyl substituent was examined and a specific relationship between the length of the alkyl chain and activity was observed.

Cyanoacrylate Inhibitors of the Hill Reaction III. Stereochemical and Electronic Aspects of Inhibitor Binding