Micellar catalysis in the retro-Knoevenagel reaction of ethyl-𝛼-cyanocinnamates

Journal of Chemical Sciences

K Rajasekaran1¹  A Sarathi¹  S Ramalakshmi¹ 

[1] Post-Graduate Department of Chemistry, Virudhunagar Hindu Nadars’ Senthikumara Nadar (VHNSN) College, Virudhunagar 626 001$$

关键词: Ethyl 𝛼-cyanocinnamate;    micellar catalysis;    retro-Knoevenagel reaction;    hydrophobicity.;   

DOI  :  

来源: Indian Academy of Sciences

【 摘 要 】

Kinetics of base catalysed hydrolytic cleavage of ethyl 𝛼-cyanocinnamate (ECC) and several para-substituted ECC have been investigated spectrophotometrically in the presence of anionic surfactant sodium laurylsulphate (NaLS). The rate of cleavage of ECC was retarded by NaLS. The pseudo-first order rate constants, 𝑘obs, correlate with the Hammett $sigma^{+}_{p}$ - constants. The ρ+ value (0.86) in aqueous medium is less than ρ+ value (1.11) in 0.02 M NaLS. Kinetic data were analysed by Menger-Portnoy and Piszkiwicz model. The substrate-micelle binding constants, 𝐾𝑠, correlate with the Hammett 𝜎-constants and Hansch hydrophobicity constants - 𝜋 of the substituents.

【 授权许可】

Unknown