62268-73-9

Basic information

• Product Name: diphenylcarbene
• Synonyms: diphenylcarbene
• CAS NO: 62268-73-9
• Molecular Weight: 166.222
• Mol File: 62268-73-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: diphenylcarbene(CAS DataBase Reference)
• NIST Chemistry Reference: diphenylcarbene(62268-73-9)
• EPA Substance Registry System: diphenylcarbene(62268-73-9)

Safety Data

• Hazardous Substances Data: 62268-73-9(Hazardous Substances Data)

Upstream product

• 908093-98-1 diazodiphenylmethane 

Downstream Products

• 3315-60-4 methanolate 
• 4471-17-4 diphenylmethyl radical 
• 34493-33-9 thiobenzophenone ketyl radical 
• 77381-38-5 C₁₄H₁₀S₂^(1-) 
• 51314-23-9 methyl diphenylmethyl radical 
• 30951-98-5 2-phenyl-propan-2-ide 
• 2143-68-2 methoxyl radical 
• 64723-96-2 acetic acid methyl ester; deprotonated form 
• 64723-97-3 1,1,1-trifluoroacetone enolate anion 
• 14477-72-6 trifluoroacetate 
• 2154-50-9 ethoxy radical 
• 2264-21-3 trifluoromethyl radical 
• 70677-38-2 ethyl diphenylacetate anion 
• 119-61-9 benzophenone 

Relevant articles and documents

Generation, Thermodynamics, and Chemistry of the Diphenylcarbene Anion Radical (Ph2C.-)

Dissociative electron attachment with Ph2C=N produced Ph2C.- (m/z 166).The reactions of Ph2C.- with potential proton donors of known gas-phase acidity were used to bracket PA(Ph2C.-) = 380 +/- 2 kcal mol-1 from which ΔHf0(Ph2C.-) = 81.8 +/- 2 kcal mol-1 was calculated.The reactions of Ph2C.- with CH3OH and C2H5OH proceeded with major and minor amounts, respectively, of a H2.+-transfer channel, forming Ph2CH2, RCHO, and an electron.The kinetic nucleophilicity of Ph2C.- in SN2 displacement reactions with CH3X and C2H5X molecules was shown to be medium, which requires a significant intrinsic barrier in these reaction.The reactions of Ph2C.- with various aldehydes, ketones, and esters were fast and established two principal product-forming channels: (1) H+ transfer if the neutral reactant contains activated C-H bonds and (2) carbonyl addition followed by radical β-fragmentation of one of the groups originally attached to the carbonyl carbon.The order for the ease of radical β-fragmentation in the tetrahedral intermediates was RO > alkyl >> H, and CO2CH3 > CH3.Since the reactions of Ph2C.- with the simple esters HCO2CH3 and CH3CO2CH3 were fast, it should now be possible to examine the reactions of carbonyl-containing organic molecules, which are expected to react slower than these esters and obtain their relative reactivities.