Tetrahydrofuran

Formula: C₄H₈O
Molecular weight: 72.1057
IUPAC Standard InChI: InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2
IUPAC Standard InChIKey: WYURNTSHIVDZCO-UHFFFAOYSA-N
CAS Registry Number: 109-99-9
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: Furan, tetrahydro-; Butane α,δ-oxide; Butane, 1,4-epoxy-; Cyclotetramethylene oxide; Furanidine; Oxacyclopentane; Oxolane; Tetramethylene oxide; THF; Hydrofuran; Tetrahydrofuraan; Tetrahydrofuranne; Tetraidrofurano; NCI-C60560; Rcra waste number U213; UN 2056; Diethylene oxide; Dynasolve 150; Tetrahydrofurane; THF (tetrahydrofuran); NSC 57858
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References, Notes

Data compiled as indicated in comments:
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	-44.03 ± 0.17	kcal/mol	Cm	Pell and Pilcher, 1965	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_gas	-605.44 ± 0.16	kcal/mol	Cm	Pell and Pilcher, 1965	Corresponding Δ_fHº_gas = -44.02 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_gas	72.11 ± 0.41	cal/mol*K	N/A	Clegg G.A., 1968	Other third-law entropy values at 298.15 K evaluated from calorimetric data are 299.1 J/molK [ Chao J., 1986] and 288(1) J/molK [ Lebedev B.V., 1978].; GT

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
9.159	50.	Dorofeeva O.V., 1992	p=1 bar. Selected thermodynamic functions agree well with results of other statistical calculations [ Scott D.W., 1970, Chao J., 1986].; GT
9.641	100.
10.67	150.
12.46	200.
16.61	273.15
18.32 ± 0.24	298.15
18.45	300.
25.590	400.
32.130	500.
37.639	600.
42.225	700.
46.071	800.
49.321	900.
52.084	1000.
54.441	1100.
56.458	1200.
58.191	1300.
59.682	1400.
60.973	1500.

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
20.35 ± 0.041	328.15	Hossenlopp I.A., 1981	GT
21.84 ± 0.043	349.15
25.363 ± 0.050	399.15
28.774 ± 0.057	449.15
31.950 ± 0.065	500.15

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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_cH°_liquid	-598.90 ± 0.50	kcal/mol	Ccb	Cass, Fletcher, et al., 1958	Reanalyzed by Cox and Pilcher, 1970, Original value = -598.8 ± 0.5 kcal/mol; Corresponding Δ_fHº_liquid = -50.56 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-597.80 ± 0.20	kcal/mol	Ccb	Skuratov, Strepikheev, et al., 1957	Reanalyzed by Cox and Pilcher, 1970, Original value = -598.0 ± 0.1 kcal/mol; Combustion at 293 K; Corresponding Δ_fHº_liquid = -51.66 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	48.71	cal/mol*K	N/A	Lebedev, Lityagov, et al., 1979	DH
S°_liquid	48.73	cal/mol*K	N/A	Lebedev, Rabinovich, et al., 1978	DH
S°_liquid	48.73	cal/mol*K	N/A	Lebedev and Lityagov, 1977	DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
29.66	298.15	Costas and Patterson, 1985	T = 283.15, 298.15, 313.15 K.; DH
29.66	298.15	Costas and Patterson, 1985, 2	DH
29.379	298.15	Inglese, Castagnolo, et al., 1981	DH
29.532	298.15	Kiyohara, D'Arcy, et al., 1979	DH
29.61	298.15	Lebedev, Rabinovich, et al., 1978	T = 8 to 322 K.; DH
29.61	298.15	Lebedev and Lityagov, 1977	T = 5 to 400 K.; DH
28.7	298.15	Bonner and Cerutti, 1976	DH
28.80	298.	Conti, Gianni, et al., 1976	DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References, Notes

Data compiled as indicated in comments:
DH - Eugene S. Domalski and Elizabeth D. Hearing
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
T_boil	339. ± 1.	K	AVG	N/A	Average of 16 out of 17 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	165.1	K	N/A	Hayduk, Laudie, et al., 1973	Uncertainty assigned by TRC = 0.5 K; TRC
T_fus	164.15	K	N/A	Brooks and Pilcher, 1959	Uncertainty assigned by TRC = 1. K; TRC
T_fus	164.63	K	N/A	Boord, Greenlee, et al., 1946	Uncertainty assigned by TRC = 0.2 K; TRC
T_fus	164.05	K	N/A	Dolliver, Gresham, et al., 1938	Uncertainty assigned by TRC = 0.4 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_triple	164.76	K	N/A	Wilhoit, Chao, et al., 1985	Uncertainty assigned by TRC = 0.05 K; TRC
T_triple	164.76	K	N/A	Lebedev, Lityagov, et al., 1979	Uncertainty assigned by TRC = 0.02 K; TRC
T_triple	164.76	K	N/A	Lebedev, Rabinovich, et al., 1978, 2	Uncertainty assigned by TRC = 0.02 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_c	540.2	K	N/A	Majer and Svoboda, 1985
T_c	540.1	K	N/A	Cheng, McCoubrey, et al., 1962	Uncertainty assigned by TRC = 0.3 K; Visual (5-cm 2-mm bore tubes) in nitrate-nitrite bath, TE or TH cal. vs NPL thermometer.; TRC
T_c	541.	K	N/A	Kobe, Ravicz, et al., 1956	Uncertainty assigned by TRC = 1.5 K; TRC
Quantity	Value	Units	Method	Reference	Comment
P_c	51.22	atm	N/A	Kobe, Ravicz, et al., 1956	Uncertainty assigned by TRC = 0.5000 atm; TRC
Quantity	Value	Units	Method	Reference	Comment
V_c	0.225	l/mol	N/A	Kobe, Ravicz, et al., 1956	Uncertainty assigned by TRC = 0.003 l/mol; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	7.686	kcal/mol	N/A	Majer and Svoboda, 1985
Δ_vapH°	7.6	kcal/mol	C	Hossenlopp and Scott, 1981	AC
Δ_vapH°	7.86	kcal/mol	N/A	Moiseev and Antonova, 1970	Based on data from 224. to 360. K.; AC
Δ_vapH°	7.6	kcal/mol	V	Cass, Fletcher, et al., 1958	ALS

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
7.125	339.1	N/A	Majer and Svoboda, 1985
7.72	305.	N/A	Loras, Aucejo, et al., 2001	Based on data from 290. to 339. K.; AC
7.91	288.	A	Stephenson and Malanowski, 1987	Based on data from 273. to 339. K.; AC
6.9	414.	A	Stephenson and Malanowski, 1987	Based on data from 399. to 479. K.; AC
7.07	482.	A	Stephenson and Malanowski, 1987	Based on data from 467. to 541. K.; AC
7.77 ± 0.05	288.	N/A	Borisov and Chugunova, 1976	Based on data from 235. to 340. K.; AC
7.36	320.	N/A	Rivenq, 1975	Based on data from 302. to 339. K.; AC
7.84	288.	N/A	Koizumi and Ouchi, 1970	Based on data from 273. to 308. K. See also Boublik, Fried, et al., 1984.; AC
7.62	311.	N/A	Scott D.W., 1970	Based on data from 296. to 373. K. See also Boublik, Fried, et al., 1984.; AC
7.8	293.	V	Skuratov, Strepikheev, et al., 1957	Combustion at 293 K; ALS
7.60	313.	N/A	Klages and Möhler, 1948	Based on data from 293. to 313. K. See also Cass, Fletcher, et al., 1958, 2.; AC

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
T_r = reduced temperature (T / T_c)

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Temperature (K)	A (kcal/mol)	β	T_c (K)	Reference	Comment
302. to 339.	11.02	0.2699	540.2	Majer and Svoboda, 1985

Antoine Equation Parameters

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

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Temperature (K)	A	B	C	Reference	Comment
296.29 to 372.8	4.11547	1202.942	-46.818	Scott D.W., 1970	Coefficents calculated by NIST from author's data.

Enthalpy of fusion

Δ_fusH (kcal/mol)	Temperature (K)	Reference	Comment
2.041	164.76	Lebedev, Rabinovich, et al., 1978	DH
2.041	164.76	Lebedev and Lityagov, 1977	DH
2.04	164.8	Acree, 1991	AC

Entropy of fusion

Δ_fusS (cal/mol*K)	Temperature (K)	Reference	Comment
12.4	164.76	Lebedev, Rabinovich, et al., 1978	DH
12.39	164.76	Lebedev and Lityagov, 1977	DH

Enthalpy of phase transition

ΔH_trs (kcal/mol)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
2.041	164.76	crystaline, I	liquid	Lebedev, Lityagov, et al., 1979	DH

Entropy of phase transition

ΔS_trs (cal/mol*K)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
12.39	164.76	crystaline, I	liquid	Lebedev, Lityagov, et al., 1979	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:

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering 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
MS - José A. Martinho Simões

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

C₄H₉O⁺ + Tetrahydrofuran = (C₄H₉O⁺ • )

By formula: C₄H₉O⁺ + C₄H₈O = (C₄H₉O⁺ • C₄H₈O)

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	29.9	kcal/mol	PHPMS	Hiraoka and Takimoto, 1986	gas phase; M
Δ_rH°	32.5	kcal/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	29.1	cal/mol*K	PHPMS	Hiraoka and Takimoto, 1986	gas phase; M
Δ_rS°	32.2	cal/mol*K	N/A	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	22.9	kcal/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M

C₄H₁₁O⁺ + Tetrahydrofuran = (C₄H₁₁O⁺ • )

By formula: C₄H₁₁O⁺ + C₄H₈O = (C₄H₁₁O⁺ • C₄H₈O)

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	30.4	kcal/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	29.5	cal/mol*K	N/A	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	21.6	kcal/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M

C₅H₁₁O⁺ + Tetrahydrofuran = (C₅H₁₁O⁺ • )

By formula: C₅H₁₁O⁺ + C₄H₈O = (C₅H₁₁O⁺ • C₄H₈O)

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	30.1	kcal/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, 86 KEE/CAS; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	29.4	cal/mol*K	N/A	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, 86 KEE/CAS; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	21.3	kcal/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, 86 KEE/CAS; M

(C₄H₉O⁺ • Tetrahydrofuran ) + = (C₄H₉O⁺ • 2)

By formula: (C₄H₉O⁺ • C₄H₈O) + C₄H₈O = (C₄H₉O⁺ • 2C₄H₈O)

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	7.6	kcal/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	18.	cal/mol*K	N/A	Hiraoka, Takimoto, et al., 1987	gas phase; Entropy change calculated or estimated; M

C₆H₅NO₂^- + Tetrahydrofuran = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₄H₈O = (C₆H₅NO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	3.2 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
3.2	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₇H₄N₂O₂^- + Tetrahydrofuran = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₄H₈O = (C₇H₄N₂O₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1.4 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
1.4	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₆H₄FNO₂^- + Tetrahydrofuran = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₄H₈O = (C₆H₄FNO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	3.2 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
3.2	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₆H₄FNO₂^- + Tetrahydrofuran = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₄H₈O = (C₆H₄FNO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	2.9 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
2.9	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₆H₄FNO₂^- + Tetrahydrofuran = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₄H₈O = (C₆H₄FNO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	2.8 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
2.8	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₇H₇NO₂^- + Tetrahydrofuran = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + C₄H₈O = (C₇H₇NO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	3.0 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
3.0	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₇H₇NO₂^- + Tetrahydrofuran = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + C₄H₈O = (C₇H₇NO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	3.1 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
3.1	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₇H₇NO₂^- + Tetrahydrofuran = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + C₄H₈O = (C₇H₇NO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	3.1 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
3.1	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₇H₄N₂O₂^- + Tetrahydrofuran = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₄H₈O = (C₇H₄N₂O₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	3.7 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
3.7	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₇H₄N₂O₂^- + Tetrahydrofuran = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₄H₈O = (C₇H₄N₂O₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	2.1 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
2.1	308.	PHPMS	Chowdhury, 1987	gas phase; M

+ 2 = Tetrahydrofuran

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, 2	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -36.63 ± 0.12 kcal/mol; At 355 °K; ALS

+ Tetrahydrofuran = ( • )

By formula: Mg⁺ + C₄H₈O = (Mg⁺ • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	66. ± 5.	kcal/mol	ICR	Operti, Tews, et al., 1988	gas phase; switching reaction,Thermochemical ladder(Mg+)CH3OH; M

Tetrahydrofuran (solution) + (solution) = C₉H₈O₆W (solution) + (solution)

By formula: C₄H₈O (solution) + C₆O₆W (solution) = C₉H₈O₆W (solution) + CO (solution)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	14.5 ± 1.0	kcal/mol	PC	Nakashima and Adamson, 1982	solvent: Tetrahydrofuran; MS

C₁₄H₂₁MnO₂ (solution) + Tetrahydrofuran (solution) = C₁₁H₁₃MnO₃ (solution) + (solution)

By formula: C₁₄H₂₁MnO₂ (solution) + C₄H₈O (solution) = C₁₁H₁₃MnO₃ (solution) + C₇H₁₆ (solution)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-16.1 ± 1.4	kcal/mol	PAC	Klassen, Selke, et al., 1990	solvent: Heptane; MS

C₁₂H₁₆CrO₅ (solution) + Tetrahydrofuran (solution) = C₉H₈CrO₆ (solution) + (solution)

By formula: C₁₂H₁₆CrO₅ (solution) + C₄H₈O (solution) = C₉H₈CrO₆ (solution) + C₇H₁₆ (solution)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-12.4 ± 1.2	kcal/mol	PAC	Yang, Peters, et al., 1986	solvent: Heptane; MS

+ = Tetrahydrofuran

By formula: C₄H₆O + H₂ = C₄H₈O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-25.57 ± 0.30	kcal/mol	Chyd	Allinger, Glaser, et al., 1981	liquid phase; solvent: Hexane; ALS

+ = Tetrahydrofuran

By formula: H₂ + C₄H₆O = C₄H₈O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-27.98 ± 0.31	kcal/mol	Chyd	Allinger, Glaser, et al., 1981	liquid phase; solvent: Hexane; ALS

Tetrahydrofuran (solution) + C₂₀H₃₀Sm (solution) = C₂₄H₃₈OSm (solution)

By formula: C₄H₈O (solution) + C₂₀H₃₀Sm (solution) = C₂₄H₃₈OSm (solution)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-7.29 ± 0.41	kcal/mol	RSC	Nolan, Stern, et al., 1989	solvent: Toluene; MS

C₂₄H₃₈OSm (solution) + Tetrahydrofuran (solution) = C₂₈H₄₆O₂Sm (solution)

By formula: C₂₄H₃₈OSm (solution) + C₄H₈O (solution) = C₂₈H₄₆O₂Sm (solution)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-4.9 ± 1.0	kcal/mol	RSC	Nolan, Stern, et al., 1989	solvent: Toluene; MS

C₂₄H₃₉Si₃U (solution) + Tetrahydrofuran (solution) = C₂₈H₄₇OSi₃U (solution)

By formula: C₂₄H₃₉Si₃U (solution) + C₄H₈O (solution) = C₂₈H₄₇OSi₃U (solution)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-9.8 ± 0.2	kcal/mol	RSC	Schock, Seyam, et al., 1988	solvent: Toluene; MS

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, References, Notes

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₄H₈O⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	9.40 ± 0.02	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	196.5	kcal/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	189.9	kcal/mol	N/A	Hunter and Lias, 1998	HL

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.38 ± 0.05	EI	Holmes and Lossing, 1991	LL
9.38	PE	Behan, Dean, et al., 1976	LLK
9.41	S	Doucet, Sauvageau, et al., 1972	LLK
9.42 ± 0.01	S	Hernandez, 1963	RDSH
9.54	PI	Watanabe, Nakayama, et al., 1962	RDSH
9.74	PE	Kimura, Katsumata, et al., 1981	Vertical value; LLK
9.71	PE	Gerson, Worley, et al., 1978	Vertical value; LLK
9.65	PE	Schmidt and Schweig, 1974	Vertical value; LLK
9.53	PE	Pignataro and Distefano, 1974	Vertical value; LLK
9.57 ± 0.02	PE	Bain, Bunzli, et al., 1973	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₂H₂⁺	17.3 ± 0.3	?	EI	Gallegos and Kiser, 1962	RDSH
C₂H₃⁺	16.1 ± 0.3	?	EI	Gallegos and Kiser, 1962	RDSH
C₂H₃O⁺	12.8 ± 0.2	?	EI	Gallegos and Kiser, 1962	RDSH
C₂H₄O⁺	12.27	C₂H₄	EI	Collin and Conde-Caprace, 1966	RDSH
C₂H₅⁺	15.8 ± 0.2	?	EI	Gallegos and Kiser, 1962	RDSH
C₃H₃⁺	18.7 ± 0.6	?	EI	Gallegos and Kiser, 1962	RDSH
C₃H₄⁺	15.2 ± 0.3	?	EI	Gallegos and Kiser, 1962	RDSH
C₃H₅⁺	13.72	?	EI	Collin and Conde-Caprace, 1966	RDSH
C₃H₆⁺	11.54	?	EI	Collin and Conde-Caprace, 1966	RDSH
C₄H₇O⁺	10.44	H	EI	Collin and Conde-Caprace, 1966	RDSH

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes

Data compiled as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C₄H₉O⁺ + Tetrahydrofuran = (C₄H₉O⁺ • )

By formula: C₄H₉O⁺ + C₄H₈O = (C₄H₉O⁺ • C₄H₈O)

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	29.9	kcal/mol	PHPMS	Hiraoka and Takimoto, 1986	gas phase; M
Δ_rH°	32.5	kcal/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	29.1	cal/mol*K	PHPMS	Hiraoka and Takimoto, 1986	gas phase; M
Δ_rS°	32.2	cal/mol*K	N/A	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	22.9	kcal/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M

(C₄H₉O⁺ • Tetrahydrofuran ) + = (C₄H₉O⁺ • 2)

By formula: (C₄H₉O⁺ • C₄H₈O) + C₄H₈O = (C₄H₉O⁺ • 2C₄H₈O)

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	7.6	kcal/mol	PHPMS	Hiraoka, Takimoto, et al., 1987	gas phase; Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	18.	cal/mol*K	N/A	Hiraoka, Takimoto, et al., 1987	gas phase; Entropy change calculated or estimated; M

C₄H₁₁O⁺ + Tetrahydrofuran = (C₄H₁₁O⁺ • )

By formula: C₄H₁₁O⁺ + C₄H₈O = (C₄H₁₁O⁺ • C₄H₈O)

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	30.4	kcal/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	29.5	cal/mol*K	N/A	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	21.6	kcal/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M

C₅H₁₁O⁺ + Tetrahydrofuran = (C₅H₁₁O⁺ • )

By formula: C₅H₁₁O⁺ + C₄H₈O = (C₅H₁₁O⁺ • C₄H₈O)

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	30.1	kcal/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, 86 KEE/CAS; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	29.4	cal/mol*K	N/A	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, 86 KEE/CAS; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	21.3	kcal/mol	ICR	Larson and McMahon, 1982	gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, 86 KEE/CAS; M

C₆H₄FNO₂^- + Tetrahydrofuran = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₄H₈O = (C₆H₄FNO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	3.2 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
3.2	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₆H₄FNO₂^- + Tetrahydrofuran = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₄H₈O = (C₆H₄FNO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	2.9 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
2.9	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₆H₄FNO₂^- + Tetrahydrofuran = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₄H₈O = (C₆H₄FNO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	2.8 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
2.8	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₆H₅NO₂^- + Tetrahydrofuran = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₄H₈O = (C₆H₅NO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	3.2 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
3.2	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₇H₄N₂O₂^- + Tetrahydrofuran = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₄H₈O = (C₇H₄N₂O₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	2.1 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
2.1	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₇H₄N₂O₂^- + Tetrahydrofuran = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₄H₈O = (C₇H₄N₂O₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	3.7 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
3.7	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₇H₄N₂O₂^- + Tetrahydrofuran = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₄H₈O = (C₇H₄N₂O₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1.4 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
1.4	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₇H₇NO₂^- + Tetrahydrofuran = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + C₄H₈O = (C₇H₇NO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	3.0 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
3.0	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₇H₇NO₂^- + Tetrahydrofuran = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + C₄H₈O = (C₇H₇NO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	3.1 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
3.1	308.	PHPMS	Chowdhury, 1987	gas phase; M

C₇H₇NO₂^- + Tetrahydrofuran = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + C₄H₈O = (C₇H₇NO₂^- • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	3.1 ± 1.6	kcal/mol	IMRE	Chowdhury, Grimsrud, et al., 1987	gas phase; Free energy affinity at 35°C.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
3.1	308.	PHPMS	Chowdhury, 1987	gas phase; M

+ Tetrahydrofuran = ( • )

By formula: Mg⁺ + C₄H₈O = (Mg⁺ • C₄H₈O)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	66. ± 5.	kcal/mol	ICR	Operti, Tews, et al., 1988	gas phase; switching reaction,Thermochemical ladder(Mg+)CH3OH; M

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Notes

Pell and Pilcher, 1965
Pell, A.S.; Pilcher, G., Measurements of heats of combustion by flame calorimetry. Part 3.-Ethylene oxide, trimethylene oxide, tetrahydrofuran and tetrahydropy, Trans. Faraday Soc., 1965, 61, 71-77. [all data]

Clegg G.A., 1968
Clegg G.A., Thermodynamics of polymerization of heterocyclic compounds. II. The heat capacity, entropy, enthalpy and free energy of polytetrahydrofuran, Polymer, 1968, 9, 501-511. [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]

Lebedev B.V., 1978
Lebedev B.V., Thermodynamic properties of tetrahydrofuran from 8 to 322 K, J. Chem. Thermodyn., 1978, 10, 321-329. [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]

Scott D.W., 1970
Scott D.W., Tetrahydrofuran: vibrational assignment, chemical thermodynamic properties, and vapor pressure, J. Chem. Thermodyn., 1970, 2, 833-837. [all data]

Hossenlopp I.A., 1981
Hossenlopp I.A., Vapor heat capacities and enthalpies of vaporization of six organic compounds, J. Chem. Thermodyn., 1981, 13, 405-414. [all data]

Cass, Fletcher, et al., 1958
Cass, R.C.; Fletcher, S.E.; Mortimer, C.T.; Springall, H.D.; White, T.R., Heats of combustion and molecular structure. Part V. The mean bond energy term for the C-O bond in ethers, and the structures of some cyclic ethers, J. Chem. Soc., 1958, 1406-1410. [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]

Skuratov, Strepikheev, et al., 1957
Skuratov, S.M.; Strepikheev, A.A.; Kozina, M.P., About the reaction activity of five and six-membered heterocyclic compounds, Dokl. Akad. Nauk SSSR, 1957, 117, 452-454. [all data]

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Lebedev, B.V.; Lityagov, V.Ya.; Krentsina, T.I.; Milov, V.I., Thermodynamic properties of tetrahydrofuran in the range 8-322 K, Zhur. Fiz. Khim., 1979, 53, 264-265. [all data]

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Lebedev, B.V.; Lityagov, V.Ya., Calorimetric study of tetrahydrofuran and its polymerization in the temperature range 0-400°K, Vysokomol. Soedin., 1977, A19, 2283-2290. [all data]

Costas and Patterson, 1985
Costas, M.; Patterson, D., Heat capacities of water + organic-solvent mixtures, J. Chem. Soc., Faraday Trans. 1, 1985, 81, 2381-2398. [all data]

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Costas, M.; Patterson, D., Self-association of alcohols in inert solvents, J. Chem. Soc., Faraday Trans. 1, 1985, 81, 635-654. [all data]

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Kiyohara, D'Arcy, et al., 1979
Kiyohara, O.; D'Arcy, P.J.; Benson, G.C., Ultrasonic velocities, compressibilities, and heat capacities of water + tetrahydrofuran mixtures at 298.15K, Can. J. Chem., 1979, 57, 1006-1010. [all data]

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Hayduk, W.; Laudie, H.; Smith, O.H., Viscosity, Freezing Point, Vapor-Liquid Equilibria, and Other Properties of Aqueous-Tetrahydrofuran Solutions, J. Chem. Eng. Data, 1973, 18, 373-6. [all data]

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Cass, R.C.; Fletcher, S.E.; Mortimer, C.T.; Springall, H.D.; White, T.R., 281. Heats of combustion and molecular structure. Part V. The mean bond energy term for the C?O bond in ethers, and the structures of some cyclic ethers, J. Chem. Soc., 1958, 1406, https://doi.org/10.1039/jr9580001406 . [all data]

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Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References

Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
IE (evaluated)	Recommended ionization energy
P_c	Critical pressure
S°_gas	Entropy of gas at standard conditions
S°_liquid	Entropy of liquid at standard conditions
T	Temperature
T_boil	Boiling point
T_c	Critical temperature
T_fus	Fusion (melting) point
T_triple	Triple point temperature
V_c	Critical volume
ΔH_trs	Enthalpy of phase transition
ΔS_trs	Entropy of phase transition
Δ_cH°_gas	Enthalpy of combustion of gas at standard conditions
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_fusS	Entropy of fusion
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
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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