Furan

Formula: C₄H₄O
Molecular weight: 68.0740
IUPAC Standard InChI: InChI=1S/C4H4O/c1-2-4-5-3-1/h1-4H
IUPAC Standard InChIKey: YLQBMQCUIZJEEH-UHFFFAOYSA-N
CAS Registry Number: 110-00-9
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: Divinylene oxide; Furfuran; Oxacyclopentadiene; Oxole; Tetrole; Furane; Furfurane; NCI-C56202; Rcra waste number U124; UN 2389; 1,4-Epoxy-1,3-butadiene
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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	-6.62	kcal/mol	N/A	Zaheeruddin and Lodhi, 1991	Value computed using Δ_fH_liquid° value of -55.4 kj/mol from Zaheeruddin and Lodhi, 1991 and Δ_vapH° value of 27.6 kj/mol from Guthrie, Scott, et al., 1952.; DRB
Δ_fH°_gas	-8.29	kcal/mol	Ccb	Guthrie, Scott, et al., 1952	ALS
Δ_fH°_gas	-7.12	kcal/mol	N/A	Landrieu, Baylocq, et al., 1929	Value computed using Δ_fH_liquid° value of -57.5 kj/mol from Landrieu, Baylocq, et al., 1929 and Δ_vapH° value of 27.6 kj/mol from Guthrie, Scott, et al., 1952.; DRB

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
7.949	50.	Dorofeeva O.V., 1992	p=1 bar. Selected entropies and heat capacities are in good agreement with those obtained in other statistical calculations [ Guthrie G.B., 1952, Bak B., 1955, Rico M., 1967, Soptrajanov B., 1968, Chao J., 1986, Klots T.D., 1994].; GT
8.014	100.
8.697	150.
10.42	200.
14.20	273.15
15.63 ± 0.36	298.15
15.74	300.
21.22	400.
25.770	500.
29.343	600.
32.168	700.
34.448	800.
36.329	900.
37.906	1000.
39.245	1100.
40.385	1200.
41.367	1300.
42.213	1400.
42.947	1500.

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
16.80	317.25	Guthrie G.B., 1952	GT
19.15	358.20
21.51	402.20
23.80	449.20
25.449	487.20

Condensed phase thermochemistry data

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

Data compiled as indicated in comments:
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°_liquid			Ccb	Zaheeruddin and Lodhi, 1991	uncertain value: -13.23 kcal/mol; ALS
Δ_fH°_liquid	-14.90	kcal/mol	Ccb	Guthrie, Scott, et al., 1952	ALS
Δ_fH°_liquid	-13.73	kcal/mol	Ccb	Landrieu, Baylocq, et al., 1929	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid			Ccb	Zaheeruddin and Lodhi, 1991	uncertain value: -499.608 kcal/mol; ALS
Δ_cH°_liquid	-497.97	kcal/mol	Ccb	Guthrie, Scott, et al., 1952	Corresponding Δ_fHº_liquid = -14.86 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-499.1	kcal/mol	Ccb	Landrieu, Baylocq, et al., 1929	Corresponding Δ_fHº_liquid = -13.7 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	42.220	cal/mol*K	N/A	Guthrie, Scott, et al., 1952, 2	DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
27.380	298.15	Guthrie, Scott, et al., 1952, 2	T = 11 to 300 K.; 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
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar

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Individual Reactions

C₄H₅O⁺ + Furan = (C₄H₅O⁺ • Furan )

By formula: C₄H₅O⁺ + C₄H₄O = (C₄H₅O⁺ • C₄H₄O)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	10.	kcal/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; Δ_rH<; M
Δ_rH°	19.	kcal/mol	PHPMS	Meot-Ner (Mautner), Ross, et al., 1985	gas phase; Entropy change calculated or estimated, Δ_rH<; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	32.	cal/mol*K	N/A	Meot-Ner (Mautner), Ross, et al., 1985	gas phase; Entropy change calculated or estimated, Δ_rH<; M

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
6.6	382.	PHPMS	Meot-Ner (Mautner), Ross, et al., 1985	gas phase; Entropy change calculated or estimated, Δ_rH<; M

C₄H₃O^- + = Furan

By formula: C₄H₃O^- + H⁺ = C₄H₄O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	391.07 ± 0.36	kcal/mol	G+TS	Grabowski and Owusu	gas phase; B
Δ_rH°	388.2 ± 3.1	kcal/mol	G+TS	DePuy, Kass, et al., 1988	gas phase; Order:H2O < furan < 2-Me-furan < MeOH. D exchange indicates anion at C-2.; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	382.90 ± 0.20	kcal/mol	IMRE	Grabowski and Owusu	gas phase; B
Δ_rG°	380.0 ± 3.0	kcal/mol	IMRB	DePuy, Kass, et al., 1988	gas phase; Order:H2O < furan < 2-Me-furan < MeOH. D exchange indicates anion at C-2.; B

Furan + 2 =

By formula: C₄H₄O + 2H₂ = C₄H₈O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-36.12 ± 0.12	kcal/mol	Chyd	Dolliver, Gresham, et al., 1938	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -36.63 ± 0.12 kcal/mol; At 355 °K; ALS

C₄H₄O⁺ + Furan = (C₄H₄O⁺ • Furan )

By formula: C₄H₄O⁺ + C₄H₄O = (C₄H₄O⁺ • C₄H₄O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	17.2	kcal/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	23.7	cal/mol*K	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; M

(C₄H₄O⁺ • Furan ) + Furan = (C₄H₄O⁺ • 2 Furan )

By formula: (C₄H₄O⁺ • C₄H₄O) + C₄H₄O = (C₄H₄O⁺ • 2C₄H₄O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	7.	kcal/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; Δ_rH<; M

+ Furan = ( • Furan )

By formula: Na⁺ + C₄H₄O = (Na⁺ • C₄H₄O)

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
11.7	298.	IMRE	McMahon and Ohanessian, 2000	Anchor alanine=39.89; RCD

References

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

Zaheeruddin and Lodhi, 1991
Zaheeruddin, M.; Lodhi, Z.H., Enthalpies of formation of some cyclic compounds, Phys. Chem. (Peshawar Pak.), 1991, 10, 111-118. [all data]

Guthrie, Scott, et al., 1952
Guthrie, G.B., Jr.; Scott, D.W.; Hubbard, W.N.; Katz, C.; McCullough, J.P.; Gross, M.E.; Williamson, K.D.; Waddington, G., Thermodynamic properties of furan, J. Am. Chem. Soc., 1952, 74, 4662-46. [all data]

Landrieu, Baylocq, et al., 1929
Landrieu, P.; Baylocq, F.; Johnson, J.R., Etude thermochimique dans la serie furanique, Bull. Soc. Chim. France, 1929, 45, 36-49. [all data]

Dorofeeva O.V., 1992
Dorofeeva O.V., Ideal gas thermodynamic properties of oxygen heterocyclic compounds. Part 1. Three-membered, four-membered and five-membered rings, Thermochim. Acta, 1992, 194, 9-46. [all data]

Guthrie G.B., 1952
Guthrie G.B., Jr., Thermodynamic properties of furan, J. Am. Chem. Soc., 1952, 74, 4662-4669. [all data]

Bak B., 1955
Bak B., Infrared absorption spectra of alpha and beta monodeutero, and alpha, alpha' dideutero furan vapors. Heat capacity and entropy of furan, Acta Chem. Scand., 1955, 9, 749-762. [all data]

Rico M., 1967
Rico M., Fundamental vibrations of furan and deuterated derivatives, J. Mol. Spectrosc., 1967, 24, 133-148. [all data]

Soptrajanov B., 1968
Soptrajanov B., Thermodynamic functions of furan and deuterated furans, Croat. Chem. Acta, 1968, 40, 241-245. [all data]

Chao J., 1986
Chao J., Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties, J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]

Klots T.D., 1994
Klots T.D., Complete vapor phase assignment for the fundamental vibrations of furan, pyrrole and thiophene, Spectrochim. Acta, 1994, A50, 765-795. [all data]

Guthrie, Scott, et al., 1952, 2
Guthrie, G.B., Jr.; Scott, D.W.; Hubbard, W.N.; Katz, C.; McCullough, J.P.; Gross, M.E.; Williamson, K.D.; Waddington, G., Thermodynamic properties of furan, J. Am. Chem. Soc., 1952, 74, 4662-4669. [all data]

Hiraoka, Takimoto, et al., 1987
Hiraoka, K.; Takimoto, H.; Yamabe, S., Stabilities and Structures in Cluster Ions of Five-Membered Heterocyclic Compounds Containing O, N and S Atoms, J. Am. Chem. Soc., 1987, 109, 24, 7346, https://doi.org/10.1021/ja00258a018 . [all data]

Meot-Ner (Mautner), Ross, et al., 1985
Meot-Ner (Mautner), M.; Ross, M.M.; Campana, J.E., Stable Hydrogen - Bonded Isomers of Covalent Ions, J. Am. Chem. Soc., 1985, 107, 4835. [all data]

Grabowski and Owusu
Grabowski, J.J.; Owusu, D., , as cited in 98CLI/WEN. [all data]

DePuy, Kass, et al., 1988
DePuy, C.H.; Kass, S.R.; Bean, G.P., Formation and Reactions of Heteroaromatic Anions in the Gas Phase, J. Org. Chem., 1988, 53, 19, 4427, https://doi.org/10.1021/jo00254a001 . [all data]

Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E., Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds, J. Am. Chem. Soc., 1938, 60, 440-450. [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]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [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,liquid	Constant pressure heat capacity of liquid
S°_liquid	Entropy of liquid at standard conditions
T	Temperature
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid 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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