Chemical Properties of [2.2]Paracyclophane (CAS 1633-22-3)

InChI

InChI=1S/C16H16/c1-2-14-4-3-13(1)9-10-15-5-7-16(8-6-15)12-11-14/h1-8H,9-12H2

InChI Key

OOLUVSIJOMLOCB-UHFFFAOYSA-N

Formula

C16H16

SMILES

c1cc2ccc1CCc1ccc(cc1)CC2

Molecular Weight¹

208.30

CAS

1633-22-3

Other Names

• Cyclobis(benzene-1,4-dimethylene)
• Di-1,4-xylylene
• Di-p-xylylene
• Tricyclo[8.2.2.2(4,7)]hexadeca-4,6,10,12,13,15-hexaene
• tricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaene

• Δ_cH°_solid : Standard solid enthalpy of combustion (kJ/mol).
• C_p,gas : Ideal gas heat capacity (J/mol×K).
• C_p,solid : Solid phase heat capacity (J/mol×K).
• η : Dynamic viscosity (Pa×s).
• 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).
• log₁₀WS : Log10 of Water solubility in mol/l.
• logP_oct/wat : Octanol/Water partition coefficient.
• McVol : McGowan's characteristic volume (ml/mol).
• P_c : Critical Pressure (kPa).
• P_vap : Vapor pressure (kPa).
• S°_{solid,1 bar} : Solid phase molar entropy at standard conditions (J/mol×K).
• T_boil : Normal Boiling Point Temperature (K).
• T_c : Critical Temperature (K).
• T_fus : Normal melting (fusion) point (K).
• V_c : Critical Volume (m³/kmol).
• ¹: Molecular weight from the IUPAC atomic weights tables.

Physical Properties

Property	Value	Unit	Source
ΔcH°solid	[-8737.00; -8727.57]	kJ/mol
ΔcH°solid	-8729.50 ± 1.80	kJ/mol	NIST
ΔcH°solid	-8727.57 ± 0.63	kJ/mol	NIST
ΔcH°solid	-8737.00 ± 4.00	kJ/mol	NIST
ΔfG°	345.76	kJ/mol	Joback Calculated Property
ΔfH°gas	[241.00; 244.70]	kJ/mol
ΔfH°gas	244.70 ± 2.10	kJ/mol	NIST
ΔfH°gas	241.00 ± 4.20	kJ/mol	NIST
ΔfH°gas	241.30 ± 4.30	kJ/mol	NIST
ΔfH°solid	[144.70; 154.00]	kJ/mol
ΔfH°solid	146.70 ± 2.80	kJ/mol	NIST
ΔfH°solid	144.70 ± 0.88	kJ/mol	NIST
ΔfH°solid	154.00 ± 4.00	kJ/mol	NIST
ΔfusH°	19.46	kJ/mol	Joback Calculated Property
ΔsubH°	[87.30; 98.00]	kJ/mol
ΔsubH°	98.00	kJ/mol	NIST
ΔsubH°	96.20 ± 4.20	kJ/mol	NIST
ΔsubH°	96.30	kJ/mol	NIST
ΔsubH°	96.20 ± 4.20	kJ/mol	NIST
ΔsubH°	87.30	kJ/mol	NIST
ΔvapH°	57.48	kJ/mol	Joback Calculated Property
IE	[7.60; 8.20]	eV
IE	7.80	eV	NIST
IE	7.80	eV	NIST
IE	7.60	eV	NIST
IE	7.80	eV	NIST
IE	8.20	eV	NIST
IE	8.10	eV	NIST
IE	8.10	eV	NIST
IE	8.00	eV	NIST
IE	8.08	eV	NIST
log10WS	-4.55		Crippen Calculated Property
logPoct/wat	3.570		Crippen Calculated Property
McVol	177.920	ml/mol	McGowan Calculated Property
Pc	2673.54	kPa	Joback Calculated Property
S°solid,1 bar	265.68	J/mol×K	NIST
Tboil	644.48	K	Joback Calculated Property
Tc	901.88	K	Joback Calculated Property
Tfus	366.62	K	Joback Calculated Property
Vc	0.665	m3/kmol	Joback Calculated Property

Temperature Dependent Properties

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[456.99; 551.01]	J/mol×K	[644.48; 901.88]
Cp,gas	456.99	J/mol×K	644.48	Joback Calculated Property
Cp,gas	476.19	J/mol×K	687.38	Joback Calculated Property
Cp,gas	493.79	J/mol×K	730.28	Joback Calculated Property
Cp,gas	509.95	J/mol×K	773.18	Joback Calculated Property
Cp,gas	524.78	J/mol×K	816.08	Joback Calculated Property
Cp,gas	538.42	J/mol×K	858.98	Joback Calculated Property
Cp,gas	551.01	J/mol×K	901.88	Joback Calculated Property
Cp,solid	[248.10; 252.70]	J/mol×K	[298.15; 300.00]
Cp,solid	252.70	J/mol×K	298.15	NIST
Cp,solid	252.34	J/mol×K	298.15	NIST
Cp,solid	248.10	J/mol×K	300.00	NIST
η	[0.0002378; 0.0018114]	Pa×s	[366.62; 644.48]
η	0.0018114	Pa×s	366.62	Joback Calculated Property
η	0.0010682	Pa×s	412.93	Joback Calculated Property
η	0.0007007	Pa×s	459.24	Joback Calculated Property
η	0.0004965	Pa×s	505.55	Joback Calculated Property
η	0.0003728	Pa×s	551.86	Joback Calculated Property
η	0.0002926	Pa×s	598.17	Joback Calculated Property
η	0.0002378	Pa×s	644.48	Joback Calculated Property
ΔfusH	0.21	kJ/mol	323.20	NIST
ΔsubH	[92.90; 99.60]	kJ/mol	[363.00; 381.40]
ΔsubH	92.90 ± 0.84	kJ/mol	363.00	NIST
ΔsubH	96.40 ± 1.50	kJ/mol	381.00	NIST
ΔsubH	99.60 ± 1.80	kJ/mol	381.40	NIST

Correlations

Property	Value	Unit	Temperature (K)	Source
Pvap	[1.33; 202.68]	kPa	[475.36; 571.10]	The Yaw...
Equation			ln(Pvp) = A + B/(T + C)
Coefficient A			3.02554e+01
Coefficient B			-1.42454e+04
Temperature range, min.			475.36
Temperature range, max.			571.10
Pvap	1.33	kPa	475.36	Calculated Property
Pvap	2.57	kPa	486.00	Calculated Property
Pvap	4.81	kPa	496.64	Calculated Property
Pvap	8.79	kPa	507.27	Calculated Property
Pvap	15.64	kPa	517.91	Calculated Property
Pvap	27.21	kPa	528.55	Calculated Property
Pvap	46.30	kPa	539.19	Calculated Property
Pvap	77.20	kPa	549.82	Calculated Property
Pvap	126.24	kPa	560.46	Calculated Property
Pvap	202.68	kPa	571.10	Calculated Property

Similar Compounds

Find more compounds similar to [2.2]Paracyclophane.

Sources

• Crippen Method
• Crippen Method
• Joback Method
• McGowan Method
• NIST Webbook
• The Yaws Handbook of Vapor Pressure

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