155821-76-4

Basic information

• Product Name: meso-1,4-Diphenyl-2,3-dipiperidino-1,4-butandion
• CAS NO: 155821-76-4
• Molecular Weight: 404.552
• Mol File: 155821-76-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: meso-1,4-Diphenyl-2,3-dipiperidino-1,4-butandion(CAS DataBase Reference)
• NIST Chemistry Reference: meso-1,4-Diphenyl-2,3-dipiperidino-1,4-butandion(155821-76-4)
• EPA Substance Registry System: meso-1,4-Diphenyl-2,3-dipiperidino-1,4-butandion(155821-76-4)

Safety Data

• Hazardous Substances Data: 155821-76-4(Hazardous Substances Data)

Upstream product

• 110-89-4 piperidine 
• 959-28-4 1,4-diphenylbut-2-ene-1,4-dione 

Relevant articles and documents

Substituent Effects on the Strength of C-C Bonds, 14. - Kinetic and Thermodynamic Stability of 2,3-Bis(dialkylamino)-1,4-diketones - Energy of Stabilization of α-Dialkylamino α-Carbonylalkyl Radicals with Capto-dative Substituents

The equilibrium constants and rate constants for the dissociation of the 2,3-bis(dialkylamino)-1,4-diketone diastereomers meso- and DL-7a and 7b were measured over a temperature range of 40 deg C.From the enthalpies of dissociation ΔHDiss and ethalpies of activation ΔH(excit.) and the strain enthalpies of 7 the bond dissociation enthalpies BDE(C-C) of 7 were determined.By comparison with the dissociation enthalpies of Ct-Ct alkanes the change of these BDEs(C-C) by the capto-dative substitution was determined to be 85.4 kJ mol-1 (20.4 kcal mol-1).The heats of formation ΔHf0(g) of a series of amino ketones 8 were determined from their heats of combustion and their heats of evaporation.From the ΔHf0(g) values in combination with MM2 calculations of their strain enthalpies strain-free increments CHn2-n> with n = 0, 1, 2 were derived and geminal interaction enthalpies in the ground states were obtained thereof.The radical stabilization enthalpy RSE of 6 was deduced from the ΔBDE(C-C) values and the ground state effect to be 73.6 kJ mol-1 (17.6 kcal mol-1).From these data and the radical stabilization enthalpies RSE of α-aminoalkyl radicals (4.2 kJ mol-1) and α-carbonyl radicals (28.9 kJ mol-1) a synergetic radical stabilization enthalpy of 40.5 kJ mol-1 (9.7 kcal mol-1) is deduced.This number combines "extra" resonance stabilization and general inductive or anomeric geminal substituent interaction in the radicals.The crystal structure of meso-7a has been determined by X-ray diffraction methods. - Key Words: C-C Bond cleavage, kinetics of / Heats of formation / Radicals, stability of / Capto-dative effect / Geminal substituents, energetic interaction of