1,3-Dioxane
- Formula: C4H8O2
- Molecular weight: 88.1051
- IUPAC Standard InChIKey: VDFVNEFVBPFDSB-UHFFFAOYSA-N
- CAS Registry Number: 505-22-6
- 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: m-Dioxane; m-Dioxin, dihydro-; 1,3-Dioxacyclohexane; 1,3-Propanediol formal
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Gas phase thermochemistry 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -338.4 ± 1.1 | kJ/mol | Ccr | Bystrm and Mansson, 1982 | ALS |
ΔfH°gas | -349.6 | kJ/mol | N/A | Pihlaja and Luoma, 1968 | Value computed using ΔfHliquid° value of -384.6±1.8 kj/mol from Pihlaja and Luoma, 1968 and ΔvapH° value of 35.0 kj/mol from Pihlaja and Heikkila, 1967.; DRB |
ΔfH°gas | -350. ± 2. | kJ/mol | Ccb | Pihlaja and Heikkila, 1967 | ALS |
ΔfH°gas | -341. ± 2. | kJ/mol | Ccb | Snelson and Skinner, 1961 | ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
33.72 | 50. | Dorofeeva O.V., 1992 | p=1 bar. Selected values are in close agreement with statistically calculated values given in [ Thermodynamics Research Center, 1997]. The value of -(G-Ho)/T at 298.15 K obtained from absolute intensity measurements in the microwave spectrum [ Curl R.F., 1973] is 2 J/mol*K higher than that obtained by [ Dorofeeva O.V., 1992].; GT |
40.36 | 100. | ||
50.54 | 150. | ||
61.93 | 200. | ||
81.80 | 273.15 | ||
89.4 ± 1.5 | 298.15 | ||
89.97 | 300. | ||
121.54 | 400. | ||
150.80 | 500. | ||
175.77 | 600. | ||
196.67 | 700. | ||
214.19 | 800. | ||
228.96 | 900. | ||
241.46 | 1000. | ||
252.10 | 1100. | ||
261.17 | 1200. | ||
268.93 | 1300. | ||
275.61 | 1400. | ||
281.37 | 1500. |
Condensed phase thermochemistry 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:
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 | -377.5 ± 1.1 | kJ/mol | Ccr | Bystrm and Mansson, 1982 | ALS |
ΔfH°liquid | -384.6 ± 1.8 | kJ/mol | Ccb | Pihlaja and Luoma, 1968 | ALS |
ΔfH°liquid | -385. ± 1. | kJ/mol | Ccb | Pihlaja and Heikkila, 1967 | ALS |
ΔfH°liquid | -376.6 ± 0.84 | kJ/mol | Ccb | Snelson and Skinner, 1961 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2333. ± 10. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
143.9 | 298. | Conti, Gianni, et al., 1976 | DH |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 378.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 37. ± 4. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
378.2 | 1.01 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
39. | 293. | V | Skuratov, Strepikheev, et al., 1957 | combustion of liq at 293 K; ALS |
Reaction thermochemistry 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 by: 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
By formula: 2C4H8O2 = C8H16O4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -9.9 ± 2.8 | kJ/mol | Eqk | Szymanski, 1991 | solid phase |
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
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 825.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 796.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.33 | EI | Collin and Conde, 1966 | RDSH |
10.12 | PE | Asfandiarov and Zykov, 1983 | Vertical value; LBLHLM |
10.12 | PE | Kobayashi and Nagakura, 1973 | Vertical value; LLK |
10.1 | PE | Sweigart and Turner, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH2O+ | 11.82 | ? | EI | Collin and Conde, 1966 | RDSH |
C2H4+ | 13.16 | ? | EI | Collin and Conde, 1966 | RDSH |
C3H5O+ | 12.17 | ? | EI | Collin and Conde, 1966 | RDSH |
C3H6O+ | 11.12 | CH2O | EI | Collin and Conde, 1966 | RDSH |
C3H7O+ | 12.17 | CHO | EI | Collin and Conde, 1966 | RDSH |
C4H7O2+ | 10.42 | H | EI | Collin and Conde, 1966 | RDSH |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-2853 |
NIST MS number | 228233 |
Gas Chromatography
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apiezon L | 120. | 701. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | Apiezon L | 160. | 720. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apieson L | 120. | 707. | Kurdina, Markovich, et al., 1969 | not specified, not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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]
Pihlaja and Luoma, 1968
Pihlaja, K.; Luoma, S.,
Heats of formation and conformational energies of 1,3-dioxane and its methyl homologues,
Acta Chem. Scand., 1968, 22, 2401-2414. [all data]
Pihlaja and Heikkila, 1967
Pihlaja, K.; Heikkila, J.,
The configurations of isomeric 2,2,4,6-tetramethyl-1,3-dioxanes,
Acta Chem. Scand., 1967, 21, 2430-2434. [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]
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]
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]
Curl R.F., 1973
Curl R.F.,
Determination of thermodynamic functions from absolute intensity measurements in microwave spectroscopy,
J. Am. Chem. Soc., 1973, 95, 6182-6190. [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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Skuratov, Strepikheev, et al., 1957
Skuratov, S.M.; Strepikheev, A.A.; Shtekhter, S.M.; Volokhina, A.V.,
About the enthalpies of polymerization of cyclic formales,
Dokl. Akad. Nauk SSSR, 1957, 117, 263-265. [all data]
Szymanski, 1991
Szymanski, R.,
Equilibrium between 1,3 and its cyclooligomers,
Makromol. Chem., 1991, 192, 2961-2968. [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]
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]
Asfandiarov and Zykov, 1983
Asfandiarov, N.L.; Zykov, B.G.,
Photoelectron spectra of methyl-substituted 1,3-Dioxanes,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1983, 10, 2069, In original 2293. [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]
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]
Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S.,
Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]
Kurdina, Markovich, et al., 1969
Kurdina, Z.G.; Markovich, V.E.; Sakharov, V.M.,
Gas chromatography of cyclic O-containing compounds
in Gas chromatography, Issue # 10, NIITEKhim, Moscow, 1969, 128-133. [all data]
Notes
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- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid Tboil Boiling point 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 ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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