1,4-Dioxane
- Formula: C4H8O2
- Molecular weight: 88.1051
- IUPAC Standard InChI: InChI=1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2
- IUPAC Standard InChIKey: RYHBNJHYFVUHQT-UHFFFAOYSA-N
- CAS Registry Number: 123-91-1
- 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: p-Dioxane; p-Dioxan; Di(ethylene oxide); Diethylene dioxide; Diethylene ether; Dioxan; Dioxane; Dioxyethylene ether; 1,4-Diethylene dioxide; 1,4-Dioxan; 1,4-Dioxacyclohexane; Glycol ethylene ether; Tetrahydro-p-dioxin; Diokan; Dioksan; Diossano-1,4; Dioxaan-1,4; Dioxan-1,4; Dioxane-1,4; Dioxanne; NCI-C03689; Tetrahydro-1,4-dioxin; p-Dioxin, tetrahydro-; Rcra waste number U108; UN 1165; 1,4-Dioxin, tetrahydro-; 1,4-Diethyleneoxide; Glycol ethylene ether 8; NE 220; NSC 8728
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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 |
|---|---|---|---|---|---|
| ΔfH°gas | -75.36 ± 0.19 | kcal/mol | Ccr | Bystrm and Mansson, 1982 | Reanalyzed by Cox and Pilcher, 1970, Original value = -75.6 ± 0.2 kcal/mol; ALS |
| ΔfH°gas | -76.0 ± 0.4 | kcal/mol | Ccb | Snelson and Skinner, 1961 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°gas | 71.680 | cal/mol*K | N/A | Stull D.R., 1969 | GT |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 8.090 | 50. | Dorofeeva O.V., 1992 | p=1 bar. Selected values are in close agreement with statistical values calculated by [ Ellestad O.H., 1971, Thermodynamics Research Center, 1997]. Heat capacities calculated by [ Malherbe F.E., 1952] are 2-3 J/mol*K larger than those given here.; GT |
| 9.814 | 100. | ||
| 12.36 | 150. | ||
| 15.21 | 200. | ||
| 20.15 | 273.15 | ||
| 22.02 ± 0.36 | 298.15 | ||
| 22.16 | 300. | ||
| 29.818 | 400. | ||
| 36.800 | 500. | ||
| 42.696 | 600. | ||
| 47.600 | 700. | ||
| 51.704 | 800. | ||
| 55.158 | 900. | ||
| 58.083 | 1000. | ||
| 60.571 | 1100. | ||
| 62.696 | 1200. | ||
| 64.517 | 1300. | ||
| 66.083 | 1400. | ||
| 67.435 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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 |
|---|---|---|---|---|---|
| ΔfH°liquid | -84.88 ± 0.21 | kcal/mol | Ccr | Bystrm and Mansson, 1982 | ALS |
| ΔfH°liquid | -84.5 ± 0.2 | kcal/mol | Ccb | Snelson and Skinner, 1961 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -564.59 ± 0.24 | kcal/mol | Ccr | Bystrm and Mansson, 1982 | Corresponding ΔfHºliquid = -84.878 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -564.99 ± 0.12 | kcal/mol | Ccb | Snelson and Skinner, 1961 | Corresponding ΔfHºliquid = -84.47 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -560.76 | kcal/mol | Ccb | Roth and Meyer, 1933 | Corrected for pressure and temperature; Corresponding ΔfHºliquid = -88.70 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -522.65 | kcal/mol | Ccb | Herz and Lorentz, 1929 | Corresponding ΔfHºliquid = -126.81 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 46.99 | cal/mol*K | N/A | Jacobs and Parks, 1934 | Extrapolation below 90 K, 11.12 cal/mol*K.; DH |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 35.767 | 298.15 | Grolier, Roux-Desgranges, et al., 1993 | DH |
| 35.987 | 298.15 | Trejo, Costas, et al., 1991 | DH |
| 35.7287 | 298.15 | Barta, Kooner, et al., 1989 | DH |
| 36.006 | 298.15 | Grolier, Inglese, et al., 1984 | DH |
| 36.035 | 298.15 | Inglese, Grolier, et al., 1984 | DH |
| 35.786 | 298.15 | Inglese, Castagnolo, et al., 1981 | DH |
| 35.61 | 298. | Murthy and Subrahmanyam, 1979 | DH |
| 35.6 | 298.15 | Bonner and Cerutti, 1976 | DH |
| 33.51 | 298. | Conti, Gianni, et al., 1976 | DH |
| 37.19 | 298. | Deshpande and Bhatagadde, 1971 | T = 298 to 318 K.; DH |
| 35.35 | 298.15 | Hyder Khan and Subrahmanyam, 1971 | T = 298; 313 K.; DH |
| 35.35 | 298. | Subrahmanyam and Khan, 1969 | DH |
| 36.561 | 298.2 | Jacobs and Parks, 1934 | T = 92 to 299 K. Value is unsmoothed experimental datum.; DH |
| 34.89 | 291. | Roth and Meyer, 1933 | T = 8 to 28°C.; DH |
| 37.00 | 296. | Herz and Lorentz, 1929 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
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
By formula: C3H7O+ + C4H8O2 = (C3H7O+ • C4H8O2)
Bond type: Hydrogen bonds of the type OH-O between organics
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 30.0 | 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 |
| ΔrS° | 30.2 | 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 |
| ΔrG° | 21.0 | 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 |
By formula: C4H9O2+ + C4H8O2 = (C4H9O2+ • C4H8O2)
Bond type: Hydrogen bonds of the type OH-O between organics
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 30.9 | 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 |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 31.5 | 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 |
| ΔrG° | 21.5 | 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 |
+
= (
•
)
By formula: Na+ + C4H8O2 = (Na+ • C4H8O2)
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 24.1 | 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
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Bystrm and Mansson, 1982
Bystrm, K.; Mansson, M.,
Enthalpies of formation of some cyclic 1,3- and 1,4-Di- and poly-ethers: Thermochemical strain in the -O-C-O and -O-C-C-O- groups,
J. Chem. Soc. Perkin Trans. 2, 1982, 565. [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]
Snelson and Skinner, 1961
Snelson, A.; Skinner, H.A.,
Heats of combustion: sec-propanol, 1,4-dioxan, 1,3-dioxan and tetrahydropyran,
Trans. Faraday Soc., 1961, 57, 2125-2131. [all data]
Stull D.R., 1969
Stull D.R., Jr.,
The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]
Dorofeeva O.V., 1992
Dorofeeva O.V.,
Ideal gas thermodynamic properties of oxygen heterocyclic compounds. Part 2. Six-membered, seven-membered and eight-membered rings,
Thermochim. Acta, 1992, 200, 121-150. [all data]
Ellestad O.H., 1971
Ellestad O.H.,
The vibrational spectra of 1,4-dioxan-d0 and 1,4-dioxan-d8,
Spectrochim. Acta, 1971, A27, 1025-1048. [all data]
Thermodynamics Research Center, 1997
Thermodynamics Research Center,
Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]
Malherbe F.E., 1952
Malherbe F.E.,
The infrared and Raman spectra of p-dioxane,
J. Am. Chem. Soc., 1952, 74, 4408-4410. [all data]
Roth and Meyer, 1933
Roth, W.A.; Meyer, I.,
Einige physikalisch-chemische konstanten des dioxans,
Z. Electrochem., 1933, 39, 35-37. [all data]
Herz and Lorentz, 1929
Herz, W.; Lorentz, E.,
Physikalisch-chemische Untersuchungen an Dioxan,
Z. Phys. Chem., 1929, 140, 406-422. [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]
Grolier, Roux-Desgranges, et al., 1993
Grolier, J.-P.E.; Roux-Desgranges, G.; Berkane, M.; Jimenez, E.; Wilhelm, E.,
Heat capacities and densities of mixtures of very polar substances 2. Mixtures containing N,N-dimethylformamide,
J. Chem. Thermodynam., 1993, 25(1), 41-50. [all data]
Trejo, Costas, et al., 1991
Trejo, L.M.; Costas, M.; Patterson, D.,
Excess heat capacity of organic mixtures, Internat. DATA Series,
Selected Data Mixt., 1991, Ser. [all data]
Barta, Kooner, et al., 1989
Barta, L.; Kooner, Z.S.; Hepler, L.G.; Roux-Desgranges, G.; Grolier, J.-P.E.,
Thermodynamics of complex formation in chloroform and 1,4-dioxane,
Can. J. Chem., 1989, 67, 1225-1229. [all data]
Grolier, Inglese, et al., 1984
Grolier, J.-P.E.; Inglese, A.; Wilhelm, E.,
Excess molar heat capacities of (1,4-dioxane + an n-alkane): an unusual composition dependence,
J. Chem. Thermodynam., 1984, 16, 67-71. [all data]
Inglese, Grolier, et al., 1984
Inglese, A.; Grolier, J.-P.E.; Wilhelm, E.,
Excess volumes and excess heat capacities of oxane + cyclohexane and 1,4-dioxane + cyclohexane,
Fluid Phase Equilibria, 1984, 15, 287-294. [all data]
Inglese, Castagnolo, et al., 1981
Inglese, A.; Castagnolo, M.; Dell'Atti, A.; DeGiglio, A.,
Thermochim. Acta, 1981, 77-87. [all data]
Murthy and Subrahmanyam, 1979
Murthy, N.M.; Subrahmanyam, S.V.,
Behavior of excess heat capacity of the water + p-dioxane system,
Indian J. Pure Appl. Phys., 1979, 17(9), 620-622. [all data]
Bonner and Cerutti, 1976
Bonner, O.D.; Cerutti, P.J.,
The partial molar heat capacities of some solutes in water and deuterium oxide,
J. Chem. Thermodynam., 1976, 8, 105-111. [all data]
Conti, Gianni, et al., 1976
Conti, G.; Gianni, P.; Matteoli, E.; Mengheri, M.,
Capacita termiche molari di alcuni composti organici mono- e bifunzionali nel liquido puro e in soluzione acquosa a 25C,
Chim. Ind. (Milan), 1976, 58, 225. [all data]
Deshpande and Bhatagadde, 1971
Deshpande, D.D.; Bhatagadde, L.G.,
Heat capacities at constant volume, free volumes, and rotational freedom in some liquids,
Aust. J. Chem., 1971, 24, 1817-1822. [all data]
Hyder Khan and Subrahmanyam, 1971
Hyder Khan, V.; Subrahmanyam, S.V.,
Excess thermodynamic functions of the systems: benzene + p-xylene and benzene + p-dioxan,
Trans. Faraday Soc., 1971, 67, 2282-2291. [all data]
Subrahmanyam and Khan, 1969
Subrahmanyam, S.V.; Khan, V.H.,
Thermodynamics of the system benzene - p-dioxane,
Curr. Sci., 1969, 38, 510-511. [all data]
Larson and McMahon, 1982
Larson, J.W.; McMahon, T.B.,
Formation, Thermochemistry, and Relative Stabilities of Proton - Bound dimers of Oxygen n - Donor Bases from Ion Cyclotron Resonance Solvent - Exchange Equilibria Measurements,
J. Am. Chem. Soc., 1982, 104, 23, 6255, https://doi.org/10.1021/ja00387a016
. [all data]
Grimsrud and Kebarle, 1973
Grimsrud, E.P.; Kebarle, P.,
Gas Phase Ion Equilibria Studies of the Solvation of the Hydrogen Ion by Methanol, Dimethyl Ether and Water. Effect of Hydrogen Bonding,
J. Am. Chem. Soc., 1973, 95, 24, 7939, https://doi.org/10.1021/ja00805a002
. [all data]
Lias, Liebman, et al., 1984
Lias, S.G.; Liebman, J.F.; Levin, R.D.,
Evaluated gas phase basicities and proton affinities of molecules heats of formation of protonated molecules,
J. Phys. Chem. Ref. Data, 1984, 13, 695. [all data]
Keesee and Castleman, 1986
Keesee, R.G.; Castleman, A.W., Jr.,
Thermochemical data on Ggs-phase ion-molecule association and clustering reactions,
J. Phys. Chem. Ref. Data, 1986, 15, 1011. [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:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°gas Entropy of gas at standard conditions S°liquid Entropy of liquid at standard conditions T Temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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