24561-34-0

Basic information

• Product Name: C₁₃H₁₃NO₃
• Synonyms: C₁₃H₁₃NO₃
• CAS NO: 24561-34-0
• Molecular Weight: 231.251
• Mol File: 24561-34-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₁₃H₁₃NO₃(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₃H₁₃NO₃(24561-34-0)
• EPA Substance Registry System: C₁₃H₁₃NO₃(24561-34-0)

Safety Data

• Hazardous Substances Data: 24561-34-0(Hazardous Substances Data)

Upstream product

• 18736-43-1 4-nitro-phenyl cinnamate 
• 135636-66-7 butane-2,3-dione mono-oxime 
• 4067-21-4 2,4-nitrophenyl cinnamate 
• 73789-33-0 3,4-nitrophenyl cinnamate 
• 85238-61-5 4-formylphenyl cinnamate 
• 84796-16-7 C₁₇H₁₄O₃ 

Relevant articles and documents

The α-effect in nucleophilic substitution reactions of Y-substituted-Phenyl X-substituted-cinnamates with Butane-2,3-dione monoximate

Second-order rate constants (kOx-) have been measured spectrophotometrically for nucleophilic substitution reactions of 4-nitrophenyl X-substituted-cinnamates (7a-7e) and Y-substituted-phenyl cinnamates (8a-8e) with butane-2,3-dione monoximate (Ox-) in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C. The Hammett plot for the reactions of 7a-7e consists of two intersecting straight lines while the Yukawa-Tsuno plot exhibits an excellent linearity with ρX = 0.85 and r = 0.58, indicating that the nonlinear Hammett plot is not due to a change in the rate-determining step but is caused by resonance stabilization of the ground state (GS) of the substrate possessing an electron-donating group (EDG). The Bronsted-type plot for the reactions of Y-substituted-phenyl cinnamates (8a-8e) is linear with βlg = - 0.64, which is typical of reactions reported previously to proceed through a concerted mechanism. The a-nucleophile (Ox-) is more reactive than the reference normalnucleophile (4-ClPhO-). The magnitude of the α-effect (i.e., the kOx-/k4-ClPhO- ratio) is independent of the electronic nature of the substituent X in the nonleaving group but increases linearly as the substituent Y in the leaving group becomes a weaker electron-withdrawing group (EWG). It has been concluded that the difference in solvation energy between Ox- and 4-ClPhO - (i.e., GS effect) is not solely responsible for the α-effect but stabilization of transition state (TS) through a cyclic TS structure contributes also to the Y-dependent a-effect trend (i.e., TS effect).