Chemical Properties of Tetracyanoethylene (CAS 670-54-2)

InChI

InChI=1S/C6N4/c7-1-5(2-8)6(3-9)4-10

InChI Key

NLDYACGHTUPAQU-UHFFFAOYSA-N

Formula

C6N4

SMILES

N#CC(C#N)=C(C#N)C#N

Molecular Weight¹

128.09

CAS

670-54-2

Other Names

• (NC)2CC(CN)2
• 1,1,2,2-Ethenetetracarbonitrile
• 1,1,2,2-Tetracyanoethene
• 1,1,2,2-Tetracyanoethylene
• Ethene, tetracyano-
• Ethenetetracarbonitrile
• Ethylene, tetracyano-
• Ethylenetetracarbonitrile
• NSC 24833
• TCNE
• Tetracyanoethene
• Tetrakyanethylen
• «delta»2,2'-Bimalononitrile

• ω : Acentric Factor.
• Δ_cH°_solid : Standard solid enthalpy of combustion (kJ/mol).
• C_p,gas : Ideal gas heat capacity (J/mol×K).
• EA : Electron affinity (eV).
• Δ_fG° : Standard Gibbs free energy of formation (kJ/mol).
• Δ_fH°_gas : Enthalpy of formation at standard conditions (kJ/mol).
• Δ_fH°_solid : Solid phase enthalpy of formation at standard conditions (kJ/mol).
• Δ_fusH° : Enthalpy of fusion at standard conditions (kJ/mol).
• Δ_fusH : Enthalpy of fusion at a given temperature (kJ/mol).
• Δ_subH° : Enthalpy of sublimation at standard conditions (kJ/mol).
• Δ_subH : Enthalpy of sublimation at a given temperature (kJ/mol).
• Δ_vapH° : Enthalpy of vaporization at standard conditions (kJ/mol).
• IE : Ionization energy (eV).
• logP_oct/wat : Octanol/Water partition coefficient.
• McVol : McGowan's characteristic volume (ml/mol).
• P_c : Critical Pressure (kPa).
• T_boil : Normal Boiling Point Temperature (K).
• T_c : Critical Temperature (K).
• T_fus : Normal melting (fusion) point (K).
• ¹: Molecular weight from the IUPAC atomic weights tables.

Physical Properties

Property	Value	Unit	Source
ω	0.5309		Relay (1.0) Calculated Property
ΔcH°solid	[-3033.30; -2985.00]	kJ/mol
ΔcH°solid	-2996.00 ± 2.00	kJ/mol	NIST
ΔcH°solid	-3033.30	kJ/mol	NIST
ΔcH°solid	-2985.00 ± 2.00	kJ/mol	NIST
EA	[1.70; 3.17]	eV
EA	3.16 ± 0.02	eV	NIST
EA	3.17 ± 0.20	eV	NIST
EA	2.30 ± 0.30	eV	NIST
EA	1.70 ± 0.30	eV	NIST
EA	2.03 ± 0.05	eV	NIST
EA	2.88 ± 0.06	eV	NIST
ΔfG°	595.48	kJ/mol	Joback Calculated Property
ΔfH°gas	[688.10; 714.00]	kJ/mol
ΔfH°gas	688.10	kJ/mol	NIST
ΔfH°gas	714.00	kJ/mol	NIST
ΔfH°gas	705.00 ± 6.30	kJ/mol	NIST
ΔfH°solid	[607.10; 633.00]	kJ/mol
ΔfH°solid	607.10	kJ/mol	NIST
ΔfH°solid	633.00 ± 2.00	kJ/mol	NIST
ΔfH°solid	624.00 ± 2.00	kJ/mol	NIST
ΔfusH°	14.90	kJ/mol	Joback Calculated Property
ΔsubH°	[81.00; 81.20]	kJ/mol
ΔsubH°	81.20	kJ/mol	NIST
ΔsubH°	81.00	kJ/mol	NIST
ΔvapH°	48.82	kJ/mol	Relay (1.0) Calculated Property
IE	[11.67; 11.79]	eV
IE	11.77 ± 0.01	eV	NIST
IE	11.67 ± 0.02	eV	NIST
IE	11.79 ± 0.05	eV	NIST
logPoct/wat	0.377		Crippen Calculated Property
McVol	96.620	ml/mol	McGowan Calculated Property
Pc	2979.54	kPa	Joback Calculated Property
Tboil	496.20	K	NIST
Tc	683.15	K	Relay (1.0) Calculated Property
Tfus	[471.65; 472.00]	K
Tfus	471.65	K	Jean-Claude Bradley Open Melting Point Dataset (2014, CC0) Compiled value
Tfus	472.00 ± 0.20	K	NIST

Cheméo can also estimate Critical Volume, Log10 of Water solubility in mol/l for this compound, but they fall outside the models' validated range, so they are not shown here. Open the prediction tool to compute them on demand.

Temperature Dependent Properties

Property	Value	Unit	Temperature (K)	Source
ΔfusH	[24.92; 24.92]	kJ/mol	[472.20; 472.20]
ΔfusH	24.92	kJ/mol	472.20	NIST
ΔfusH	24.92	kJ/mol	472.20	NIST
ΔsubH	[81.20; 84.30]	kJ/mol	[301.00; 352.00]
ΔsubH	84.30	kJ/mol	301.00	NIST
ΔsubH	81.20 ± 5.90	kJ/mol	350.00	NIST
ΔsubH	81.40	kJ/mol	352.00	NIST

Correlations

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[124.57; 203.67]	J/mol×K	[273.00; 1000.00]	Joback Predicted correlation
Equation			Y = A + B·T + C·T² + D·T³ + E·T⁴ Y is Cp,gas in J/mol×K, T in K
Coefficient A			5.18700e+01
Coefficient B			3.32800e-01
Coefficient C			-2.67000e-04
Coefficient D			8.60000e-08
Coefficient E			0.00000e+00
Temperature range, min.			273.00
Temperature range, max.			1000.00
Cp,gas	124.57	J/mol×K	273.00	Calculated Property
Cp,gas	140.00	J/mol×K	353.78	Calculated Property
Cp,gas	153.13	J/mol×K	434.56	Calculated Property
Cp,gas	164.24	J/mol×K	515.33	Calculated Property
Cp,gas	173.59	J/mol×K	596.11	Calculated Property
Cp,gas	181.48	J/mol×K	676.89	Calculated Property
Cp,gas	188.15	J/mol×K	757.67	Calculated Property
Cp,gas	193.90	J/mol×K	838.44	Calculated Property
Cp,gas	198.98	J/mol×K	919.22	Calculated Property
Cp,gas	203.67	J/mol×K	1000.00	Calculated Property

Similar Compounds

Find more compounds similar to Tetracyanoethylene.

Sources

• Jean-Claude Bradley Open Melting Point Dataset (2014, CC0) ChEDL chemicals 1.5.2, from Bradley, J.-C.; Williams, A.; Lang, A. Jean-Claude Bradley Open Melting Point Dataset. Figshare, 2014 (CC0).
• Cheméo Relay (1.0)
• Crippen Method
• Crippen Method
• Joback Method
• McGowan Method
• NIST Webbook

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