Pyrene

Formula: C₁₆H₁₀
Molecular weight: 202.2506
IUPAC Standard InChI: InChI=1S/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H
IUPAC Standard InChIKey: BBEAQIROQSPTKN-UHFFFAOYSA-N
CAS Registry Number: 129-00-0
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Other names: β-Pyrene; Benzo[def]phenanthrene; Pyren; Coal tar pitch volatiles:pyrene
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	225.5 ± 2.5	kJ/mol	Review	Roux, Temprado, et al., 2008	There are sufficient literature values to make a qualified recommendation where the suggested value is in good agreement with values predicted using thermochemical cycles or from reliable estimates. In general, the evaluated uncertainty limits are on the order of (2 to 4) kJ/mol.; DRB
Δ_fH°_gas	225.7 ± 1.3	kJ/mol	Ccr	Smith, Stewart, et al., 1980	ALS
Δ_fH°_gas	214.9	kJ/mol	N/A	Westrum and Wong, 1967	Value computed using Δ_fH_solid° value of 114.7±0.4 kj/mol from Westrum and Wong, 1967 and Δ_subH° value of 100.2 kj/mol from Smith, Stewart, et al., 1980.; DRB
Δ_fH°_gas	214.9	kJ/mol	N/A	Richardson and Parks, 1939	Value computed using Δ_fH_solid° value of 114.7±3.6 kj/mol from Richardson and Parks, 1939 and Δ_subH° value of 100.2 kj/mol from Smith, Stewart, et al., 1980.; DRB

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
40.30	50.	Dorofeeva O.V., 1988	These functions are also reproduced in the reference book [ Frenkel M., 1994]. Recommended entropy and heat capacity values are in close agreement with other statistically calculated values [ Smith N.K., 1980] at T=400-500 K. The disagreement increases up to 2 J/mol*K for T=200 and 600 K.; GT
62.82	100.
94.01	150.
129.90	200.
185.37	273.15
204.2 ± 1.0	298.15
205.58	300.
275.54	400.
333.59	500.
379.87	600.
416.74	700.
446.49	800.
470.86	900.
491.07	1000.
507.98	1100.
522.25	1200.
534.37	1300.
544.73	1400.
553.62	1500.

Condensed phase thermochemistry data

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Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	125.2 ± 2.3	kJ/mol	Review	Roux, Temprado, et al., 2008	There are sufficient literature values to make a qualified recommendation where the suggested value is in good agreement with values predicted using thermochemical cycles or from reliable estimates. In general, the evaluated uncertainty limits are on the order of (2 to 4) kJ/mol.; DRB
Δ_fH°_solid	125.5 ± 1.2	kJ/mol	Ccr	Smith, Stewart, et al., 1980	ALS
Δ_fH°_solid	114.7 ± 0.4	kJ/mol	Ccr	Westrum and Wong, 1967	ALS
Δ_fH°_solid	114.7 ± 3.6	kJ/mol	Ccb	Richardson and Parks, 1939	Reanalyzed by Cox and Pilcher, 1970, Original value = 112.5 kJ/mol; see Richardson, 1939; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-7850.7 ± 1.0	kJ/mol	Ccr	Smith, Stewart, et al., 1980	Corresponding Δ_fHº_solid = 125.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-7840.1 ± 0.4	kJ/mol	Ccr	Westrum and Wong, 1967	Corresponding Δ_fHº_solid = 114.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-7840.0 ± 3.5	kJ/mol	Ccb	Richardson and Parks, 1939	Reanalyzed by Cox and Pilcher, 1970, Original value = -7836.51 kJ/mol; see Richardson, 1939; Corresponding Δ_fHº_solid = 114.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	224.89	J/mol*K	N/A	Wong and Westrum, 1971	DH
S°_{solid,1 bar}	215.1	J/mol*K	N/A	Jacobs and Parks, 1934	Extrapolation below 90 K, 59.79 J/mol*K. Hump in Cp curve around 116 K, probably 2nd order transition. H = 100 J/mol.; DH

Constant pressure heat capacity of solid

C_p,solid (J/mol*K)	Temperature (K)	Reference	Comment
229.36	298.15	Smith, Stewart, et al., 1980	DH
229.70	298.15	Wong and Westrum, 1971	T = 5 to 484 K.; DH
227.65	291.1	Jacobs and Parks, 1934	T = 94 to 292 K. Value is unsmoothed experimental datum.; DH

Reaction thermochemistry data

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Data compiled by: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₁₆H₁₀⁺ + Pyrene = (C₁₆H₁₀⁺ • Pyrene )

By formula: C₁₆H₁₀⁺ + C₁₆H₁₀ = (C₁₆H₁₀⁺ • C₁₆H₁₀)

Bond type: Charge transfer bond (positive ion)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	79.9	kJ/mol	PHPMS	Meot-Ner (Mautner), 1980	gas phase; Entropy change calculated or estimated
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	120.	J/mol*K	N/A	Meot-Ner (Mautner), 1980	gas phase; Entropy change calculated or estimated

Free energy of reaction

Δ_rG° (kJ/mol)	T (K)	Method	Reference	Comment
34.	390.	PHPMS	Meot-Ner (Mautner), 1980	gas phase; Entropy change calculated or estimated

C₁₆H₁₁⁺ + Pyrene = (C₁₆H₁₁⁺ • Pyrene )

By formula: C₁₆H₁₁⁺ + C₁₆H₁₀ = (C₁₆H₁₁⁺ • C₁₆H₁₀)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	69.0	kJ/mol	PHPMS	Meot-Ner (Mautner), 1980	gas phase
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	120.	J/mol*K	PHPMS	Meot-Ner (Mautner), 1980	gas phase

Henry's Law data

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Data compiled by: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

k°_H (mol/(kg*bar))	d(ln(k_H))/d(1/T) (K)	Method	Reference
84.		L	N/A
92.		M	N/A

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Notes

Roux, Temprado, et al., 2008
Roux, M.V.; Temprado, M.; Chickos, J.S.; Nagano, Y., Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons, J. Phys. Chem. Ref. Data, 2008, 37, 4, 1855-1996. [all data]

Smith, Stewart, et al., 1980
Smith, N.K.; Stewart, R.C., Jr.; Osborn, A.G.; Scott, D.W., Pyrene: vapor pressure, enthalpy of combustion, and chemical thermodynamic properties, J. Chem. Thermodyn., 1980, 12, 919-926. [all data]

Westrum and Wong, 1967
Westrum, E.F., Jr.; Wong, S., Strain energies and thermal properties of globular and polynuclear aromatic molecules, AEC Rept. Coo-1149-92, Contract AT(11-1)-1149, 1967, 1-7. [all data]

Richardson and Parks, 1939
Richardson, J.W.; Parks, G.S., Thermal data on organic compounds. XIX. Modern combustion data for some non-volatile compounds containing carbon, hydrogen and oxygen, J. Am. Chem. Soc., 1939, 61, 3543-3546. [all data]

Dorofeeva O.V., 1988
Dorofeeva O.V., Thermodynamic Properties of Polycyclic Aromatic Hydrocarbons in the Gaseous Phase. Institute for High Temperatures, USSR Academy of Sciences, Preprint No.1-238 (in Russian), Moscow, 1988. [all data]

Frenkel M., 1994
Frenkel M., Thermodynamics of Organic Compounds in the Gas State, Vol. I, II, Thermodynamics Research Center, College Station, Texas, 1994, 1994. [all data]

Smith N.K., 1980
Smith N.K., Jr., Pyrene: vapor pressure, enthalpy of combustion, and chemical thermodynamic properties, J. Chem. Thermodyn., 1980, 12, 919-926. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Richardson, 1939
Richardson, J.W., Precise determination of the heats of combustion of some representative organic compounds, Ph.D. Thesis for Standford University, 1939, 1-122. [all data]

Wong and Westrum, 1971
Wong, W-K.; Westrum, E.F., Jr., Thermodynamics of polynuclear aromatic molecules. I. Heat capacities and enthalpies of fusion of pyrene, flouranthene, and triphenylene, J. Chem. Thermodynam., 1971, 3, 105-124. [all data]

Jacobs and Parks, 1934
Jacobs, C.J.; Parks, G.S., Thermal data on organic compounds. XIV. Some heat capacity, entropy and free energy data for cyclic substances, J. Am. Chem. Soc., 1934, 56, 1513-1517. [all data]

Meot-Ner (Mautner), 1980
Meot-Ner (Mautner), M., Dimer Cations of Polycyclic Aromatics: Experimental Bonding Energies and Resonance Stabilization, J. Phys. Chem., 1980, 84, 21, 2724, https://doi.org/10.1021/j100458a012 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References

Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
C_p,solid	Constant pressure heat capacity of solid
S°_{solid,1 bar}	Entropy of solid at standard conditions (1 bar)
T	Temperature
d(ln(k_H))/d(1/T)	Temperature dependence parameter for Henry's Law constant
k°_H	Henry's Law constant at 298.15K
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_rS°	Entropy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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