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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Other data available:
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- Gas Phase Kinetics Database
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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.

Phase change data

Go To: Top, Gas phase thermochemistry data, References, Notes

Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
T_fus	424. ± 3.	K	AVG	N/A	Average of 8 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_triple	423.81	K	N/A	Wong and Westrum, 1971	Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	92.4 ± 1.1	kJ/mol	CGC	Hanshaw, Nutt, et al., 2008	AC
Δ_vapH°	87.2 ± 1.3	kJ/mol	GC	Teodorescu, Barhala, et al., 2006	Based on data from 423. to 493. K.; AC
Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	104.5	kJ/mol	ME	Siddiqi, Siddiqui, et al., 2009	Based on data from 341. to 418. K.; AC
Δ_subH°	100.3 ± 1.0	kJ/mol	Review	Roux, Temprado, et al., 2008	There are sufficient high-quality literature values to make a good evaluation with a high degree of confidence. In general, the evaluated uncertainty limits are on the order of (0.5 to 2.5) kJ/mol.; DRB
Δ_subH°	98.5 ± 1.0	kJ/mol	DSC	Rojas and Orozco, 2003	AC
Δ_subH°	100.2 ± 0.4	kJ/mol	V	Smith, Stewart, et al., 1980	ALS
Δ_subH°	100.2	kJ/mol	N/A	Smith, Stewart, et al., 1980	DRB

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
78.6	398.	GC	Hinckley, Bidleman, et al., 1990	Based on data from 343. to 453. K.; AC
76.	428.	N/A	Sasse, Jose, et al., 1988	Based on data from 413. to 467. K.; AC
73.	528.	A	Stephenson and Malanowski, 1987	Based on data from 513. to 668. K. See also Tsypikina and Ya, 1955.; AC
76.4	440.	N/A	Smith, Stewart, et al., 1980	Based on data from 398. to 458. K.; AC

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)

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Temperature (K)	A	B	C	Reference	Comment
473.6 to 667.9	2.68713	1086.824	-262.849	Tsypkina, 1955	Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

Δ_subH (kJ/mol)	Temperature (K)	Method	Reference	Comment
103.3 ± 2.1	380.	ME	Siddiqi, Siddiqui, et al., 2009	Based on data from 341. to 418. K.; AC
103.1 ± 6.5	353.	ME	Oja and Suuberg, 1998	Based on data from 308. to 398. K.; AC
97.9	383.	GS	Nass, Lenoir, et al., 1995	Based on data from 313. to 453. K.; AC
100.3 ± 0.3	353.	PG	Sasse, Jose, et al., 1988	Based on data from 369. to 383. K.; AC
91.2 ± 0.5	303.	GS	Sonnefeld, Zoller, et al., 1983	Based on data from 283. to 323. K.; AC
100.2 ± 0.4	410.	IP	Smith, Stewart, et al., 1980	Based on data from 398. to 423. K.; AC
100.8 ± 1.5	348. to 419.	ME	Malaspina, Bardi, et al., 1974	AC
100.5	330.	ME	Hoyer and Peperle, 1958	Based on data from 298. to 363. K.; AC
94.140	344.75	V	Bradley and Cleasby, 1953	ALS
100.1 ± 1.7	351.	ME	Inokuchi, Shiba, et al., 1952	Based on data from 345. to 358. K.; AC

Enthalpy of fusion

Δ_fusH (kJ/mol)	Temperature (K)	Method	Reference	Comment
16.7	422.4	DSC	Rojas and Orozco, 2003	Based on data from 403. to 433. K.; AC
17.36	423.8	N/A	Domalski and Hearing, 1996	AC

Entropy of fusion

Δ_fusS (J/mol*K)	Temperature (K)	Reference	Comment
2.39	120.8	Domalski and Hearing, 1996	CAL
40.97	423.8	Domalski and Hearing, 1996	CAL

Enthalpy of phase transition

ΔH_trs (kJ/mol)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
0.289	120.8	crystaline, II	crystaline, I	Wong and Westrum, 1971, 2	DH
17.364	423.81	crystaline, I	liquid	Wong and Westrum, 1971, 2	DH

Entropy of phase transition

ΔS_trs (J/mol*K)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
2.30	120.8	crystaline, II	crystaline, I	Wong and Westrum, 1971, 2	DH
40.97	423.81	crystaline, I	liquid	Wong and Westrum, 1971, 2	DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

References

Go To: Top, Gas phase thermochemistry data, Phase change 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]

Wong and Westrum, 1971
Wong, W.-K.; Westrum, E.F., Thermodynamics of Polynuclear Aromatic Molecules. 1. Heat Capacities and Enthalpies of Fusion of Pyrene, Fluoranthene, and Triphenylene, J. Chem. Thermodyn., 1971, 3, 105-24. [all data]

Hanshaw, Nutt, et al., 2008
Hanshaw, William; Nutt, Marjorie; Chickos, James S., Hypothetical Thermodynamic Properties. Subcooled Vaporization Enthalpies and Vapor Pressures of Polyaromatic Hydrocarbons, J. Chem. Eng. Data, 2008, 53, 8, 1903-1913, https://doi.org/10.1021/je800300x . [all data]

Teodorescu, Barhala, et al., 2006
Teodorescu, Mariana; Barhala, Alexandru; Dragoescu, Dana, Isothermal (vapour+liquid) equilibria for the binary (cyclopentanone or cyclohexanone with 1,1,2,2-tetrachloroethane) systems at temperatures of (343.15, 353.15, and 363.15)K, The Journal of Chemical Thermodynamics, 2006, 38, 11, 1432-1437, https://doi.org/10.1016/j.jct.2006.01.010 . [all data]

Siddiqi, Siddiqui, et al., 2009
Siddiqi, M. Aslam; Siddiqui, Rehan A.; Atakan, Burak, Thermal Stability, Sublimation Pressures, and Diffusion Coefficients of Anthracene, Pyrene, and Some Metal β-Diketonates, J. Chem. Eng. Data, 2009, 54, 10, 2795-2802, https://doi.org/10.1021/je9001653 . [all data]

Rojas and Orozco, 2003
Rojas, Aarón; Orozco, Eulogio, Measurement of the enthalpies of vaporization and sublimation of solids aromatic hydrocarbons by differential scanning calorimetry, Thermochimica Acta, 2003, 405, 1, 93-107, https://doi.org/10.1016/S0040-6031(03)00139-4 . [all data]

Hinckley, Bidleman, et al., 1990
Hinckley, Daniel A.; Bidleman, Terry F.; Foreman, William T.; Tuschall, Jack R., Determination of vapor pressures for nonpolar and semipolar organic compounds from gas chromatograhic retention data, J. Chem. Eng. Data, 1990, 35, 3, 232-237, https://doi.org/10.1021/je00061a003 . [all data]

Sasse, Jose, et al., 1988
Sasse, Karim; Jose, Jacques; Merlin, Jean-Claude, A static apparatus for measurement of low vapor pressures. Experimental results on high molecular-weight hydrocarbons, Fluid Phase Equilibria, 1988, 42, 287-304, https://doi.org/10.1016/0378-3812(88)80065-7 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Tsypikina and Ya, 1955
Tsypikina, O.; Ya, J., J. Appl. Chem. USSR, 1955, 28, 167. [all data]

Tsypkina, 1955
Tsypkina, O.Y., Study of Vacuum Pressure Influence on Efficiency of Separation of Some Polynuclear Compounds of Coal Tar Rectifications, Zh. Prikl. Khim. (Moscow), 1955, 28, 2, 185-192. [all data]

Oja and Suuberg, 1998
Oja, Vahur; Suuberg, Eric M., Vapor Pressures and Enthalpies of Sublimation of Polycyclic Aromatic Hydrocarbons and Their Derivatives, J. Chem. Eng. Data, 1998, 43, 3, 486-492, https://doi.org/10.1021/je970222l . [all data]

Nass, Lenoir, et al., 1995
Nass, Karen; Lenoir, Dieter; Kettrup, Antonius, Calculation of the Thermodynamic Properties of Polycyclic Aromatic Hydrocarbons by an Incremental Procedure, Angew. Chem. Int. Ed. Engl., 1995, 34, 16, 1735-1736, https://doi.org/10.1002/anie.199517351 . [all data]

Sonnefeld, Zoller, et al., 1983
Sonnefeld, W.J.; Zoller, W.H.; May, W.E., Dynamic coupled-column liquid-chromatographic determination of ambient-temperature vapor pressures of polynuclear aromatic hydrocarbons, Anal. Chem., 1983, 55, 2, 275-280, https://doi.org/10.1021/ac00253a022 . [all data]

Malaspina, Bardi, et al., 1974
Malaspina, L.; Bardi, G.; Gigli, R., Simultaneous determination by knudsen-effusion microcalorimetric technique of the vapor pressure and enthalpy of vaporization of pyrene and 1,3,5-triphenylbenzene, The Journal of Chemical Thermodynamics, 1974, 6, 11, 1053-1064, https://doi.org/10.1016/0021-9614(74)90067-6 . [all data]

Hoyer and Peperle, 1958
Hoyer, H.; Peperle, W., Z. Elektrochem., 1958, 62, 61. [all data]

Bradley and Cleasby, 1953
Bradley, R.S.; Cleasby, T.G., The vapour pressure and lattice energy of some aromatic ring compounds, J. Am. Chem. Soc., 1953, 1690-16. [all data]

Inokuchi, Shiba, et al., 1952
Inokuchi, Hiroo; Shiba, Sukekuni; Handa, Takashi; Akamatu, Hideo, Heats of Sublimation of Condensed Polynuclear Aromatic Hydrocarbons, Bull. Chem. Soc. Jpn., 1952, 25, 5, 299-302, https://doi.org/10.1246/bcsj.25.299 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Wong and Westrum, 1971, 2
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]

Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, References

Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
T_fus	Fusion (melting) point
T_triple	Triple point temperature
ΔH_trs	Enthalpy of phase transition
ΔS_trs	Entropy of phase transition
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_fusS	Entropy of fusion
Δ_subH	Enthalpy of sublimation
Δ_subH°	Enthalpy of sublimation at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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