19219-01-3

Basic information

• Product Name: Tetracyclopropylsuccinonitrile
• Synonyms: Tetracyclopropylsuccinonitrile
• CAS NO: 19219-01-3
• Molecular Formula: C16H20 N2
• Molecular Weight: 0
• Mol File: 19219-01-3.mol

Chemical Properties

• Boiling Point: 432.7°Cat760mmHg
• Flash Point: 208.6°C
• Appearance: /
• Density: 1.314g/cm³
• Vapor Pressure: 1.08E-07mmHg at 25°C
• Refractive Index: 1.653
• CAS DataBase Reference: Tetracyclopropylsuccinonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Tetracyclopropylsuccinonitrile(19219-01-3)
• EPA Substance Registry System: Tetracyclopropylsuccinonitrile(19219-01-3)

Safety Data

• Hazardous Substances Data: 19219-01-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H20N2/c17-9-15(11-1-2-11,12-3-4-12)16(10-18,13-5-6-13)14-7-8-14/h11-14H,1-8H2

Upstream product

• 89970-08-1 α,α,α',α'-Tetracyclopropyl-1,2-hydrazindiacetonitril 
• 15813-18-0 dicyclopropyl ketazine 
• 143-33-9 sodium cyanide 
• 1121-37-5 dicyclopropyl ketone 

Relevant articles and documents

Conformational analysis of meso- and (±)-2,3-dicyano-2,3-dicyclopropylbutane and 1,2-dicyanotetracyclopropylethane

The dipole moments of meso-2,3-dicyano-2,3-dicyclopropylbutane meso-1, (±)-2,3-dicyano-2,3-dicyclopropylbutane (±)-1 and 1,2-dicyanotetracyclopropylethane 2 in carbon tetrachloride and benzene have been measured over a range of temperatures. Analyses of the relative permittivity data show that at 25°C, meso-1 and (±)-1 favour the trans form. However, replacement of the methyl groups in 1 with cyclopropyl moieties completely reverses the trans ? gauche equilibrium, such that 2 exists in 74% gauche conformation. The experimentally derived values of the energy difference between the gauche and trans conformers and the gauche/trans population quotients were compared with values predicted by molecular orbital calculations. Theory predicts that the conformational preference of the substituted dicyanoethanes is strongly influenced by solvent polarity. The crystal and molecular structures of meso-1 and 2 were determined by single-crystal X-ray diffraction methods. Both compounds exist in the trans conformation in the solid state.

Substituent Effects on the C-C Bond Strength, 6. Tetracyclopropylsuccinonitrile

The heat of formation of the title compound 5 was obtained from the heat of combustion and the heat of sublimation.The activation parameters for the thermal decomposition of 5 were measured by reaction kinetics.A resonance energy of 7.8 kcal*mol-1 is obtained for the α-cyanodicyclopropylcarbinyl radical from the known relationship between strain enthalpy and free enthalpy of activation.Due to dicyclopropylcarbinyl stabilisation this value is 2.5 kcal*mol-1 higher than expected for a simple α-cyanoalkyl radical.Structural data for 5 were obtained from force field calculations (MM2).