1,4-Dioxane

• Formula: C₄H₈O₂
• Molecular weight: 88.1051
• IUPAC Standard InChI: InChI=1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2 Copy

  
• IUPAC Standard InChIKey: RYHBNJHYFVUHQT-UHFFFAOYSA-N Copy
• 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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• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Ion clustering data
  • Vibrational and/or electronic energy levels
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
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  • Gas Phase Kinetics Database
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Phase change data

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

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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

Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C₄H₈O₂⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

Ion clustering data

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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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C₃H₇O⁺ +  = (C₃H₇O⁺ • )

By formula: C₃H₇O⁺ + C₄H₈O₂ = (C₃H₇O⁺ • C₄H₈O₂)

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

C₄H₉O₂⁺ +  = (C₄H₉O₂⁺ • )

By formula: C₄H₉O₂⁺ + C₄H₈O₂ = (C₄H₉O₂⁺ • C₄H₈O₂)

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

 +  = ( • )

By formula: Na⁺ + C₄H₈O₂ = (Na⁺ • C₄H₈O₂)

Free energy of reaction

Vibrational and/or electronic energy levels

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Takehiko Shimanouchi

Symmetry:   C_2h     Symmetry Number σ = 2

Source: Shimanouchi, 1972

Notes

References

Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, Vibrational and/or electronic energy levels, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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, 1513-17. [all data]

Cristou, Young, et al., 1991
Cristou, G.; Young, C.L.; Svejda, P., Fluid Phase Equilibria, 1991, 67, 45-53. [all data]

Glaser and Ruland, 1957
Glaser, F.; Ruland, H., Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen, Chem. Ing. Techn., 1957, 29, 772. [all data]

Kobe, Ravicz, et al., 1956
Kobe, K.A.; Ravicz, A.E.; Vohra, S.P., Critical Properties and Vapor Pressures of Some Ethers and Heterocyclic Compounds, J. Chem. Eng. Data, 1956, 1, 50. [all data]

Hojendahl, 1946
Hojendahl, K., Dielectric Constant, Viscosity, Surface Tension, and Critical Data of Boron Tribromide, Dioxane, and Ethylene Dichloride, Mat.-Fys. Medd. - K. Dan. Vidensk. Selsk., 1946, 24, 1. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [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]

Castellari, Comelli, et al., 1984
Castellari, Carlo; Comelli, Fabio; Francesconi, Romolo, Vapor-liquid equilibria in binary systems containing 1,3-dioxolane at isobaric conditions. 4. Binary mixtures of 1,3-dioxolane with 1,4-dioxane and 1,1,2,2-tetrachloroethane, J. Chem. Eng. Data, 1984, 29, 2, 126-128, https://doi.org/10.1021/je00036a008 . [all data]

Vinson and Martin, 1963
Vinson, Carl G.; Martin, Joseph J., Heat of Vaporization and Vapor Pressure of 1,4-Dioxane., J. Chem. Eng. Data, 1963, 8, 1, 74-75, https://doi.org/10.1021/je60016a021 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Gallaugher and Hibbert, 1937
Gallaugher, A.F.; Hibbert, H., Studies on reactions relating to carbohydrates and polysaccharides. LV. Vapor pressures of the polyethylene glycols and their derivatives, J. Am. Chem. Soc., 1937, 59, 2521-2525. [all data]

Hovorka, Schaefer, et al., 1936
Hovorka, Frank; Schaefer, Ralph A.; Dreisbach, Dale, The System Dioxane and Water, J. Am. Chem. Soc., 1936, 58, 11, 2264-2267, https://doi.org/10.1021/ja01302a051 . [all data]

Crenshaw, Cope, et al., 1938
Crenshaw, J.L.; Cope, A.C.; Finkelstein, N.; Rogan, R., The Dioxanates of the Mercuric Halides, J. Am. Chem. Soc., 1938, 60, 10, 2308-2311, https://doi.org/10.1021/ja01277a010 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [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]

Roth and Meyer, 1933
Roth, W.A.; Meyer, I., Einige physikalisch-chemische konstanten des dioxans, Z. Electrochem., 1933, 39, 35-37. [all data]

Jacobs and Parks, 1934, 2
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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Fraser-Monteiro, Fraser-Monteiro, et al., 1982
Fraser-Monteiro, M.L.; Fraser-Monteiro, L.; Butler, J.J.; Baer, T.; Hass, J.R., Thermochemistry and dissociation dynamics of state-selected C₄H₈O₂⁺ ions. 1. 1,4-Dioxane, J. Phys. Chem., 1982, 86, 739. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Kobayashi and Nagakura, 1973
Kobayashi, T.; Nagakura, S., Photoelectron spectra of tetrahydropyran, 1,3-dioxane, and 1,4-dioxane, Bull. Chem. Soc. Jpn., 1973, 46, 1558. [all data]

Gol'denfel'd, Korostyshevskii, et al., 1973
Gol'denfel'd, I.V.; Korostyshevskii, I.Z.; Mischanchuk, B.G.; Pokrovskii, V.A., Determination of ionization potentials of atoms and molecules using a field mass spectrometer equipped with an energy analyzer, Dokl. Akad. Nauk SSSR, 1973, 213, 626. [all data]

Sweigart and Turner, 1972
Sweigart, D.A.; Turner, D.W., Lone pair orbitals and their interactions studied by photoelectron spectroscopy. II. Equivalent orbitals in saturated oxygen and sulfur J. Heterocycl. Chem., J. Am. Chem. Soc., 1972, 94, 5599. [all data]

Collin and Conde, 1966
Collin, J.E.; Conde, G., L'ionisation et la dissociation des polyethers cycliques soumis a l'impact electronique, Bull. Classe Sci. Acad. Roy. Belg., 1966, 52, 978. [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]

Shimanouchi, 1972
Shimanouchi, T., Tables of Molecular Vibrational Frequencies Consolidated Volume II, J. Phys. Chem. Ref. Data, 1972, 6, 3, 993-1102. [all data]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, Vibrational and/or electronic energy levels, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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