1-Methacroyl-3-salicyloyl-2-hydroxy propane (MSHP) and its derivatives (methyl, methoxy, acetyl, thio, amino, chloro and bromo) have been prepared and characterised on the basis of elemental anaylsis, mass, IR, PMR and 13C-NMR spectroscopic results. Formation of MSHP obeyed second order kinetics with a first order dependence on each of the [reactant]viz., [salicylic acid] and [glycidyl methacrylate]. A structural change (substituent change) in the salicylic acid brought about a change in its reactivity during the formation of MSHP. Second order rate constants are in the order: 5-bromo<5-chloro< acetyl<H<thio<4-amino<4-methyl<4-methoxy<4-chloro. Hammett’s plot indicated a rho (p) value of 0·43. Deviation in the case ofp-chloro substituent has been explained in terms of resonance interaction energy (ΔΔG) parameters. Effective sigma (δ) value ofp-chloro has been found to be 0·86 with ΔΔGp being 1–274 cal/mol. Isokinetic temperature (β) is far be low the experimental temperature range (325–355 K) indicating the importance of entropy factors in controlling the reaction.
Volume 134, 2022
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