Kinetic reactivities of various allenic and acrylic esters in conjugate addition reactions with various amines were inves- tigated. Competition experiments showed that amines reacted selectively with allenic esters, which was also conﬁrmed by quantitative determination of the rate constants. The antibacterial activity against Staphylococcus aureus of allenic and acrylic ester derivatives were also determined. Allenic esters were found to exhibit a higher antibacterial activity than its acrylic counterparts. A correlation between the kinetic property and the antibacterial activity suggested that a conjugate addition may involve in the antibacterial mechanism of these unsaturated esters. Graphical abstract OR OR R= Ethyl, Ph, p-ClPh, p-OHPh, p-NO Ph - faster conjugate addition with amines - higher antibacterial activity Keywords Allenes Alkenes Kinetics Antibiotics Introduction probes for biological studies [5–8] as well as the design of potent therapeutics [9–13]. Therefore, it is crucial to A conjugate addition is among the most important reac- investigate factors that play roles in efﬁciency of the tions in chemistry. The reaction has been used not only in reaction. One important factor is the nature of the elec- organic synthesis [1–4], but also in the design of chemical trophile in the reaction. Unsaturated esters such as
Monatshefte für Chemie - Chemical Monthly – Springer Journals
Published: Feb 20, 2018
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