71255-82-8

Basic information

• Product Name: 2-Propenoic acid, 3-(4-methoxyphenyl)-, 4-nitrophenyl ester
• CAS NO: 71255-82-8
• Molecular Formula: C16H13NO5
• Molecular Weight: 299.283
• Mol File: 71255-82-8.mol

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-(4-methoxyphenyl)-, 4-nitrophenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-(4-methoxyphenyl)-, 4-nitrophenyl ester(71255-82-8)
• EPA Substance Registry System: 2-Propenoic acid, 3-(4-methoxyphenyl)-, 4-nitrophenyl ester(71255-82-8)

Safety Data

• Hazardous Substances Data: 71255-82-8(Hazardous Substances Data)

Upstream product

• 105650-19-9 C₁₆H₁₃NO₄ 
• 18736-43-1 4-nitro-phenyl cinnamate 
• 77614-06-3 C₁₅H₁₀ClNO₄ 
• 100-02-7 4-nitro-phenol 
• 27019-24-5 p-nitrocinnamoyl p-nitro-phenyl ester 
• 42996-84-9 p-methoxycinnamoyl chloride 

Downstream Products

• 100-02-7 4-nitro-phenol 
• 27019-24-5 p-nitrocinnamoyl p-nitro-phenyl ester 
• 77614-06-3 C₁₅H₁₀ClNO₄ 
• 18736-43-1 4-nitro-phenyl cinnamate 
• 105650-19-9 C₁₆H₁₃NO₄ 
• 431914-36-2 4-chlorophenyl 4-methoxycinnamate 

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).

Structure-reactivity correlations in nucleophilic displacement reactions of Y-substituted-phenyl X-substituted-cinnamates with Z-substituted-phenoxides

Second-order rate constants (kN) have been measured spectrophotometrically for the nucleophilic displacement reactions of 4-nitrophenyl X-substituted-cinnamates (4a-4e) and Y-substituted-phenyl cinnamates (5a-5e) with Z-substituted-phenoxide anions in 80 mol % H2O/20 mol % DMSO at 25.0 ±0.1 °C. The Hammett plot for the reactions of 4a-4e with 4-chlorophenoxide (4-ClPhO.) consists of two intersecting straight lines, which might be taken as a change in the rate-determining step (RDS). However, it has been concluded that the nonlinear Hammett plot is not due to a change in the RDS but is caused by stabilization of the ground state of substrates possessing an electron-withdrawing group in the cinnamoyl moiety through resonance interactions, since the Yukawa-Tsuno plot exhibits an excellent linear correlation with ρX = 0.89 and r = 0.58. The Bronsted-type plot for the reactions of 4-nitrophenyl cinnamate (4c) with Z-substituted-phenoxides is linear with βnuc = 0.76. The Bronsted-type plot for the reactions of Y-substituted-phenyl cinnamates (5a-5d) with 4-chlorophenoxides (4-ClPhO.) is also linear with βlg =.0.72. The Hammett plot correlated with σ-. constants for the reactions of 5a-5d results in a much better linear correlation than that correlated with σo constants, indicating that a partial negative charge develops on the O atom of the leaving aryloxide. Thus, the reactions have been concluded to proceed through a concerted mechanism.