14609-76-8

Upstream product

• 41071-24-3 4-cyanophenoxyl radical 
• 14362-44-8 iodide 
• 2042-41-3 p-bromophenoxide ion 
• 90149-61-4 p-cyanophenyl n-dodecanoate 
• 114444-46-1 C₁₄H₁₃NO 
• 767-00-0 4-cyanophenol 
• 127913-93-3 4-(1,2,3-Triphenyl-cycloprop-2-enyloxy)-benzonitrile 
• 75761-83-0 p-cyanophenyl fluorene-9-carboxylate 
• 16331-64-9 ethanolate 
• 16513-72-7 4-cyanophenyl benzoate 
• 221447-98-9 4-cyanophenyl N-isopropylbenzimidate 
• 504-24-5 4-aminopyridine 
• 417708-19-1 4-cyanophenyl bis(4-methoxyphenyl) phosphate 
• 1122-54-9 methyl (4-pyridyl) ketone 

Downstream Products

• 13031-41-9 4-cyanophenyl acetate 
• 18938-17-5 4-formylphenoxide ion 
• 16554-54-4 3-nitrophenolate anion 
• 126083-72-5 C₁₃H₆N₅O₁₀^(1-) 
• 126083-71-4 (2,2',4,4',6,6'-hexanitro-diphenyl)-methyl anion 
• 15573-51-0 3,5-Dinitro-phenol anion 
• 60154-37-2 3,4-dinitrophenoxide ion 
• 20650-73-1 2,6-dinitrophenoxide ion 
• 69173-73-5 4-Chloro-2-nitro-phenol anion 
• 60154-35-0 3-chloro-4-nitrophenolate 
• 46206-23-9 2,5-Dinitrophenolate ion 
• 14609-74-6 p-nitrophenolate 
• 102817-54-9 4-cyanophenyl diphenylphosphinate 
• 100-02-7 4-nitro-phenol 

Relevant academic research and scientific papers

Nucleophilic Addition to Olefins. 6. Structure-Reactivity Relationships in the Reactions of Substituted Benzylidene Meldrum's Acids with Water, Hydroxide Ion, and Aryl Oxide Ions

The addition of water to p-methoxybenzylidene Meldrum's Acid (1-OMe), to form an adduct (TOH-, is subject to weak general base catalysis, just as water addition to carbocations studied by Ritchie.This implies a mechanism in which the

Kinetic Study on Nucleophilic Substitution Reactions of O-Phenyl O-Y-substituted-Phenyl Thionocarbonates with 1,8-Diazabicyclo[5.4.0]undec-7-ene in Acetonitrile

Second-order rate constants (kN) for nucleophilic substitution reactions of O-phenyl O-Y-substituted-phenyl thionocarbonates (4a–4k) with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in MeCN at 25.0 ± 0.1°C are reported. The reactivity of 4a–4k decreases as basicity of the leaving group increases except O-2,4-dinitrophenyl O-phenyl thionocarbonate (4a), which is less reactive than O-3,4-dinitrophenyl O-phenyl thionocarbonate (4b) although the former possesses 2 pKa units less basic nucleofuge than the latter. The Br?nsted-type plot for the reactions of 4b–4k is linear with βlg = ?0.50, a typical βlg value for reactions reported to proceed through a concerted mechanism. The Hammett plot correlated with σY? constants for the reactions of 4b–4k results in a better linear correlation than that correlated with σYo constants. Besides, the Yukawa-Tsuno plot exhibits an excellent linear correlation with ρY = 2.12, r = 0.68 and R2 = 0.990, indicating that a negative charge develops partially on the O atom of the leaving group in the rate-determining step (RDS). Thus, the reactions have been concluded to proceed through a forced concerted mechanism. Effects of steric hindrance on reactivity and reaction mechanism are also discussed in detail.

Kinetic study on alkaline hydrolysis of Y-substituted phenyl picolinates: Effects of modification of nonleaving group from benzoyl to picolinyl on reactivity and reaction mechanism

Second-order rate constants (kOH-) for alkaline hydrolysis of Y-substituted phenyl picolinates (6a-6i) have been measured spectrophotometrically. A linear Bronsted-type plot is obtained with βlg = -0.34, which is typical for reactions reported previously to proceed through a stepwise mechanism with formation of an addition intermediate being the rate-determining step (RDS). However, σYo constants result in a much poorer Hammett correlation than σY- constants. Furthermore, the Yukawa-Tsuno plot exhibits an excellent linear correlation with ρY = 0.82 and r = 0.72, indicating that a negative charge develops partially on the O atom of the leaving group in the RDS. Thus, the reactions have been concluded to proceed through a forced concerted mechanism with a highly unstable intermediate 7. Comparison of the current kinetic data with those reported previously for the corresponding reactions of Y-substituted phenyl benzoates has revealed that modification of the nonleaving group from benzoyl to picolinyl causes not only an increase in reactivity but also a change in the reaction mechanism (i.e., from a stepwise mechanism to a forced concerted pathway).

Kinetic study on alkaline hydrolysis of Y-substituted phenyl X-substituted benzenesulfonates: Effects of changing nucleophile from azide to hydroxide ion on reactivity and transition-state structure

Second-order rate constants (kOH-) for alkaline hydrolysis of 2,4-dinitrophenyl X-substituted benzenesulfonates (1a-1f) and Y-substituted phenyl 4-nitrobezenesulfonates (2a-2g) have been measured spectrophotometrically. Comparison of kOH/

Kinetic and theoretical study on nucleofugality in the phenolysis of 3-nitrophenyl and 4-nitrophenyl 4-cyanophenyl thionocarbonates

The phenolysis of 3-nitrophenyl 4-cyanophenyl thionocarbonate (1) and 4-nitrophenyl 4-cyanophenyl thionocarbonate (2) are subjected to a kinetic investigation in order to evaluate the nucleofugality of the corresponding leaving groups. For the reaction of 2 only 4-nitrophenoxide is obtained as leaving group. For the reaction of 1 the nucleofugality ratio 3-nitrophenoxide/4-cyanophenoxide is 1/3 from the corresponding T- intermediate. Theoretical calculations confirm the experimental results. From these results it can be concluded that the non-leaving group affects the nucleofugality ratio.

Pitfalls in assessing the α-effect: Reactions of substituted phenyl methanesulfonates with HOO-, OH-, and substituted phenoxides in H2O

Toward resolving the current controversy regarding the validity of the α-effect, we have examined the reactions of Y-substituted phenyl methanesulfonates 1a-1l with HOO-, OH-, and Z-substituted phenoxides in the gas phase versus solu

Analysis of linear free-energy relationships combined with activation parameters assigns a concerted mechanism to alkaline hydrolysis of X-substituted phenyl diphenylphosphinates

A kinetic study is reported for alkaline hydrolysis of X-substituted phenyl diphenylphosphinates (1a-i). The Bronsted-type plot for the reactions of 1a-i is linear over 4.5 pKa units with βlg= -0.49, a typical βlg value for reactions which proceed through a concerted mechanism. The Hammett plots correlated with σo and σ- constants are linear but exhibit many scattered points, while the corresponding Yukawa-Tsuno plot results in excellent linear correlation with ρ= 1.42 and r=0.35. The r value of 0.35 implies that leaving-group departure is partially advanced at the rate-determining step (RDS). A stepwise mechanism, in which departure of the leaving group from an addition intermediate occurs in the RDS, is excluded since the incoming HO - ion is much more basic and a poorer nucleofuge than the leaving aryloxide. A dissociative (DN + AN) mechanism is also ruled out on the basis of the small βlg value. As the substituent X in the leaving group changes from H to 4-NO2 and 3,4-(NO2)2, ΔH≠ decreases from 11.3 kcal mol-1 to 9.7 and 8.7 kcal mol-1, respectively, while ΔS≠ varies from -22.6 cal mol-1 K-1 to -21.4 and -20.2 cal mol-1 K-1, respectively. Analysis of LFERs combined with the activation parameters assigns a concerted mechanism to the current alkaline hydrolysis of 1a-i.

Aminolyses of aryl diphenylphosphinates and diphenylphosphinothioates: Effect of modification of electrophilic center from P=O to P=S

(Chemical Equation Presented) A kinetic study is reported for aminolysis of aryl diphenylphosphinothioates (2a-i). The phosphinothioates 2a-i are less reactive than aryl diphenylphosphinates (1a-i), the oxygen analogues of 2a-i, regardless of the basicity

Reinterpretation of curved hammett plots in reaction of nucleophiles with aryl benzoates: Change in rate-determining step or mechanism versus ground-state stabilization

A kinetic study is reported for the reaction of the anionic nucleophiles OH-, CN-, and N3- with aryl benzoates containing substituents on the benzoyl as well as the aryloxy moiety, in 80 mol % H2O-20 mol % dimethyl sulfoxide at 25.0 °C. Hammett log k vs σ plots for these systems are consistently nonlinear. However, a possible traditional explanation in terms of a mechanism involving a tetrahedral intermediate with curvature resulting from a change in rate-determining step is considered but rejected. The proposed explanation involves ground-state stabilization through resonance interaction between the benzoyl substituent and the electrophilic carbonyl center in the two-stage mechanism. Accordingly, the data are nicely accommodated on the basis of the Yukawa-Tsuno equation, which gives linear plots for all three nuceophiles. Literature reports of the mechanism of acyl transfer processes are reconsidered in this light.

Kinetics and mechanism of phosphate-catalyzed hydrolysis of benzoate esters: Comparison with nucleophilic catalysis by imidazole and o-iodosobenzoate

Phosphate-catalyzed hydrolysis of 2,4-dinitrophenyl 4-X-benzoate, and 3- or 4-Y-phenyl 3,5-dinitrobenzoates, where X and Y are substituents, has been studied spectrophotometrically. The following conclusions are based on catalytic rate constants, solvent