22705-27-7

Basic information

• Product Name: phenyl 2,2,2-trideuterioacetate
• Synonyms: phenyl 2,2,2-trideuterioacetate
• CAS NO: 22705-27-7
• Molecular Weight: 139.126
• Mol File: 22705-27-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: phenyl 2,2,2-trideuterioacetate(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2,2,2-trideuterioacetate(22705-27-7)
• EPA Substance Registry System: phenyl 2,2,2-trideuterioacetate(22705-27-7)

Safety Data

• Hazardous Substances Data: 22705-27-7(Hazardous Substances Data)

Upstream product

• 1186-52-3 tetradeuterioacetic acid 
• 108-95-2 phenol 
• 19259-90-6 [2H₃]acetyl chloride 
• 3229-70-7 phenolate 
• 81408-99-3 2,4-dinitrophenyl acetate 
• 81408-98-2 p-nitrophenyl acetate-d3 

Downstream Products

• 108-95-2 phenol 
• 1759-87-1 2,2,2-trideuteroethanol 
• 1112-02-3 d⁽³⁾-acetic acid 
• 3229-70-7 phenolate 

Relevant articles and documents

A Correlation between β-Hydrogen Isotope Effects on Carbon-13 NMR Chemical Shifts in Unsaturated Systems and the Strength of Hyperconjugative Interactions

β-Hydrogen isotope effects on the carbon-13 NMR chemical shifts of the trigonal carbon in CL3C(R)=X (L=H, or D) are reported for 15 substances inwhich the positive charge density at the trigonal carbon is regulated through systematic variation of R and X.A linear relationship is found between these isotope effects and the chemical shifts of the trigonal carbons, and this is taken as evidence for dependence of the magnitude of these isotope effects upon the strength of the hyperconjugative interaction between CL3 and C(R)=X.An explanation of hyperconjugative NMR isotope effecs in terms of anharmonic carbon-hydrogen bond-bending vibrations is advanced.

Reaction Progress at the Transition State for Nucleophilic Attack on Esters

β-Deuterium isotope effects (kCH3/kCD3) at 25 deg C in aqueous solution for reaction of the following nucleophiles and substrate acetate esters are as follows: CH3CO2(-), 2,4-(NO2)2C6H3O2CCL3 (L = H,D), 0.950 +/-0.008; C6H5O(-), 4-NO2C6H4O2CCL3, 0.971 +/-0.020; C6H5O(-), 2,4-(NO2)2C6H4O2CCL3, 0.968 +/-0.009; HO(-), 4-NO2C6H4O2CCL3, 0.970 +/-0.009; HO(-), C6H5O2CCL3, 0.980 +/-0.009.These are consistent with fractions of reactant progress at the transition state of 0.37, 0.21, 0.22, 0.22, and 0.15, respectively.Agreement is reasonably good with fractions of reaction progress estimated from α-deuterium isotope effects in formate ester reactions, measured by Cordes et al.For the nucleophilic reaction of water with C6H5O2CCL3, protolytically catalyzed by CH3CO2(-), the β-D effect is 0.914 +/-0.023 (fraction of reaction progress 0.65).This corresponds well with fractions of reaction progress of 0.58-0.66 from α-D effects for carboxylate general catalysis of three formate ester hydrolyses, studied by Cordes et al.For very strong bases (pK > 12) reacting as nucleophiles, the value of βnuc(ca. 0.2) is similar to, or smaller than, the fraction of reaction progress estimated from the isotope effects (ca. 0.2-0.4).The value of βnuc for nucleophilic reactions of weaker bases (pK = ca. 8-11) is larger than the fractions of reaction progress calculated from isotope effects (0.2-0.4 while βnuc = ca. 0.7).This evidence is consistent with negative deviations both for aryloxide ions and for strongly basic nucleophiles such as alkoxide and hydroxide ions from a hypothetical line of βnuc greater than 0.2 but smaller than 0.7.The major reason for negative deviation of aryloxide ions is probably disproportionate loss of resonance energy and of alkoxide ions is disproportionate loss of solvation energy, upon nucleophilic binding at the transition state.These two factors may be linked and may not be entirely separable.