123797-23-9

Basic information

• Product Name: Ethylium, 2,2,2-trifluoro-1-methyl-1-phenyl-
• CAS NO: 123797-23-9
• Molecular Formula: C9H8F3
• Molecular Weight: 173.158
• Mol File: 123797-23-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Ethylium, 2,2,2-trifluoro-1-methyl-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethylium, 2,2,2-trifluoro-1-methyl-1-phenyl-(123797-23-9)
• EPA Substance Registry System: Ethylium, 2,2,2-trifluoro-1-methyl-1-phenyl-(123797-23-9)

Safety Data

• Hazardous Substances Data: 123797-23-9(Hazardous Substances Data)

Upstream product

• 384-64-5 3,3,3-trifluoro-2-phenylpropene 
• 112754-64-0 1-phenyl-1-(trifluoromethyl)ethyl chloride 

Relevant articles and documents

Gas-Phase Substituent Effects in Highly Electron-Deficient Systems. I. Intrinsic Stabilities of 1-Aryl-1-(trifluoromethyl)ethyl Cations

The relative stabilities of 1-aryl-1-(trifluoromethyl)ethyl cations were determined by measuring the proton-transfer equilibria of 1-aryl-1-(trifluoromethyl)ethylenes or the chloride-transfer equilibria of 1-aryl-1-(trifluoromethyl)ethyl chlorides in the gas phase. The stability of 1-phenyl-1-(trifluoromethyl)ethyl cation was found to be 16 kcal mol-1 lower than that of the α-cumyl (1-phenyl-1-methylethyl) cation. The substituent effect on the stability of this cation can be correlated in terms of the Yukawa-Tsuno equation, giving an r+ of 1.41 and a ρ of -10.0 (in log K/K0σ-1 unit). While the ρ value is nearly identical to that of the α-cumyl cation series, the r+ value is remarkably higher than the value of unity for the α-cumyl cation, indicating that such a highly electron-deficient carbocation system should be characterized by an extremely large r+ value compared with that of the stable α-cumyl cation. In addition, this r+ value agrees with that for the SN1 solvolysis of 1-aryl-1-(trifluoromethyl)ethyl tosylates. Such agreement of the r+ values between the gas phase and solvolysis reactions has been generally observed for the benzylic carbocation systems. It is concluded that the enhanced r+ value for the solvolysis of 1-aryl-1-(trifluoromethyl)ethyl tosylates must reflect the intrinsic resonance demand characteristic of the parent 1-phenyl-1-(trifluoromethyl)ethyl cation, itself, and that the extremely large ρ+ values given by a simple correlation with σ+ (r+ = 1) are an artifact due to an improper analysis of underestimating the resonance demand for such highly deactivated substrates.