Phenanthrene

Formula: C₁₄H₁₀
Molecular weight: 178.2292
IUPAC Standard InChI: InChI=1S/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H
IUPAC Standard InChIKey: YNPNZTXNASCQKK-UHFFFAOYSA-N
CAS Registry Number: 85-01-8
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.
Isotopologues:
Other names: Phenanthren; Phenanthrin; Phenantrin
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Other data available:
Data at other public NIST sites:
- Gas Phase Kinetics Database
- NIST Polycyclic Aromatic Hydrocarbon Structure Index
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References, Notes

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	202.2 ± 2.3	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_fH°_gas	201.2 ± 4.7	kJ/mol	Ccb	Steele, Chirico, et al., 1990	Δ Hfusion = 15.96±0.05 kJ/mol; ALS
Δ_fH°_gas	206.9 ± 4.6	kJ/mol	Ccb	Coleman and Pilcher, 1966	Author was aware that data differs from previously reported values; ALS
Δ_fH°_gas	203.8	kJ/mol	N/A	Bender and Farber, 1952	Value computed using Δ_fH_solid° value of 113.0 kj/mol from Bender and Farber, 1952 and Δ_subH° value of 90.8 kj/mol from Bender and Farber, 1952.; DRB
Δ_fH°_gas	163.6	kJ/mol	N/A	Richardson and Parks, 1939	Value computed using Δ_fH_solid° value of 72.8±2.6 kj/mol from Richardson and Parks, 1939 and Δ_subH° value of 90.8 kj/mol from Richardson and Parks, 1939.; DRB

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
41.35	50.	Dorofeeva O.V., 1988	These functions are also reproduced in the reference book [ Frenkel M., 1994]. Recommended values of S(T) and Cp(T) agree with those calculated by [ Kudchadker S.A., 1979] within 1.3 J/mol*K.; GT
62.23	100.
88.70	150.
119.57	200.
168.72	273.15
185.7 ± 1.0	298.15
186.91	300.
250.42	400.
303.40	500.
345.75	600.
379.61	700.
407.06	800.
429.65	900.
448.46	1000.
464.28	1100.
477.68	1200.
489.09	1300.
498.87	1400.
507.29	1500.

Condensed phase thermochemistry data

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

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	110.1 ± 2.2	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_fH°_solid	109.8 ± 1.6	kJ/mol	Ccb	Steele, Chirico, et al., 1990	Δ Hfusion = 15.96±0.05 kJ/mol; ALS
Δ_fH°_solid	116.1 ± 1.4	kJ/mol	Ccb	Coleman and Pilcher, 1966	Author was aware that data differs from previously reported values; ALS
Δ_fH°_solid	113.	kJ/mol	Ccb	Bender and Farber, 1952	ALS
Δ_fH°_solid	72.8 ± 2.6	kJ/mol	Ccb	Richardson and Parks, 1939	High level of uncertainty in the data; Reanalyzed by Cox and Pilcher, 1970, Original value = 70.88 kJ/mol; see Richardson, 1939; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-7040. ± 30.	kJ/mol	AVG	N/A	Average of 7 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	215.06	J/mol*K	N/A	Finke, Messerly, et al., 1977	DH
S°_{solid,1 bar}	211.7	J/mol*K	N/A	Huffman, Parks, et al., 1931	Extrapolation below 90 K, 65.19 J/mol*K.; DH

Constant pressure heat capacity of solid

C_p,solid (J/mol*K)	Temperature (K)	Reference	Comment
220.3	298.15	Steele, Chirico, et al., 1990	DH
220.62	298.15	Finke, Messerly, et al., 1977	T = 10 to 440 K.; DH
267.4	343.	Rastogi and Bassi, 1964	T = 343, 404 K.; DH
134.7	298.15	Ueberreiter and Orthmann, 1950	T = 293 to 368 K. Equation only.; DH
207.1	298.1	Eibert, 1944	T = 20 to 200°C, equations only, in t°C. Cp(c) = 0.2003 + 0.00306t cal/gK (20 to 98°C); Cp(liq) = 0.292 + 0.000923t cal/gK (98 to 200°C).; DH
226.4	298.1	Schmidt, 1941	T = 20 to 200°C, equations only, in t°C. Cp(c) = 0.2440 + 0.002604t - 0.000011t2 cal/gK (20 to 98°C); Cp(liq) = 0.3328 + 0.0006760t cal/gK (98 to 200°C).; DH
233.5	297.5	Huffman, Parks, et al., 1931	T = 93 to 304 K. Value is unsmoothed experimental datum.; DH

Reaction thermochemistry data

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

Data compiled as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

C₁₄H₁₀⁺ + Phenanthrene = (C₁₄H₁₀⁺ • )

By formula: C₁₄H₁₀⁺ + C₁₄H₁₀ = (C₁₄H₁₀⁺ • C₁₄H₁₀)

Bond type: Charge transfer bond (positive ion)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	74.5	kJ/mol	PHPMS	Meot-Ner (Mautner), 1980	gas phase; Entropy change calculated or estimated; M
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; M

Free energy of reaction

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

C₁₄H₁₁⁺ + Phenanthrene = (C₁₄H₁₁⁺ • )

By formula: C₁₄H₁₁⁺ + C₁₄H₁₀ = (C₁₄H₁₁⁺ • C₁₄H₁₀)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	65.7	kJ/mol	PHPMS	Meot-Ner (Mautner), 1980	gas phase; Entropy change calculated or estimated; M
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; M

Free energy of reaction

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

7 + Phenanthrene =

By formula: 7H₂ + C₁₄H₁₀ = C₁₄H₂₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-565.	kJ/mol	Eqk	Frye, 1962	gas phase; ALS

2 + Phenanthrene =

By formula: 2H₂ + C₁₄H₁₀ = C₁₄H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-130.	kJ/mol	Eqk	Frye, 1962	gas phase; ALS

4 + Phenanthrene =

By formula: 4H₂ + C₁₄H₁₀ = C₁₄H₁₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-250.	kJ/mol	Eqk	Frye, 1962	gas phase; ALS

+ Phenanthrene =

By formula: H₂ + C₁₄H₁₀ = C₁₄H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-50.	kJ/mol	Eqk	Frye, 1962	gas phase; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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]

Steele, Chirico, et al., 1990
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Hossenlopp, I.A.; Smith, N.K., Determination of ideal-gas enthalpies of formation for key compounds, Am. Inst. Chem. Eng. Symp. Ser. (AIChE Symp. Ser.), 1990, 138-154. [all data]

Coleman and Pilcher, 1966
Coleman, D.J.; Pilcher, G., Heats of combustion of biphenyl, bibenzyl, naphthalene, anthracene, and phenanthrene, Trans. Faraday Soc., 1966, 62, 821-827. [all data]

Bender and Farber, 1952
Bender, P.; Farber, J., The heats of combustion of anthracene transannular peroxide and dianthracene, J. Am. Chem. Soc., 1952, 74, 1450-1452. [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]

Kudchadker S.A., 1979
Kudchadker S.A., Chemical thermodynamic properties of anthracene and phenathrene, J. Chem. Thermodyn., 1979, 11, 1051-1059. [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]

Finke, Messerly, et al., 1977
Finke, H.L.; Messerly, J.F.; Lee, S.H.; Osborn, A.G.; Douslin, D.R., Comprehensive thermodynamic studies of seven aromatic hydrocarbons, J. Chem. Thermodyn., 1977, 9, 937-956. [all data]

Huffman, Parks, et al., 1931
Huffman, H.M.; Parks, G.S.; Barmore, M., Thermal data on organic compounds. X. Further studies on the heat capacities, entropies and free energies of hydrocarbons, J. Am. Chem. Soc., 1931, 53, 3876-3888. [all data]

Rastogi and Bassi, 1964
Rastogi, R.P.; Bassi, P.S., Mechanism of eutectic crystallization, J. Phys. Chem., 1964, 68, 2398-2406. [all data]

Ueberreiter and Orthmann, 1950
Ueberreiter, K.; Orthmann, H.-J., Specifische Wärme, spezifisches Volumen, Temperatur- und Wärme-leittähigkeit einiger disubstituierter Benzole und polycyclischer Systeme, Z. Natursforsch. 5a, 1950, 101-108. [all data]

Eibert, 1944
Eibert, J., Thesis Washington University (St. Louis), 1944. [all data]

Schmidt, 1941
Schmidt, W.R., Thesis Washington University (St. Louis), 1941. [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]

Frye, 1962
Frye, C.G., Equilibria in the hydrogenation of polycyclic aromatics, J. Chem. Eng. Data, 1962, 7, 592-595. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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
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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