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1,3-Dioxane

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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, IR Spectrum, Mass spectrum (electron ionization), 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas-80.88 ± 0.26kcal/molCcrBystrm and Mansson, 1982ALS
Deltafgas-83.56kcal/molN/APihlaja and Luoma, 1968Value computed using «DELTA»fHliquid° value of -384.6±1.8 kj/mol from Pihlaja and Luoma, 1968 and «DELTA»vapH° value of 35.0 kj/mol from Pihlaja and Heikkila, 1967.; DRB
Deltafgas-83.6 ± 0.5kcal/molCcbPihlaja and Heikkila, 1967ALS
Deltafgas-81.5 ± 0.4kcal/molCcbSnelson and Skinner, 1961ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
8.05950.Dorofeeva O.V., 1992p=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
9.646100.
12.08150.
14.80200.
19.55273.15
21.37 ± 0.36298.15
21.50300.
29.049400.
36.042500.
42.010600.
47.005700.
51.193800.
54.723900.
57.7101000.
60.2531100.
62.4211200.
64.2761300.
65.8721400.
67.2491500.

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
Deltafliquid-90.22 ± 0.26kcal/molCcrBystrm and Mansson, 1982ALS
Deltafliquid-91.92 ± 0.43kcal/molCcbPihlaja and Luoma, 1968ALS
Deltafliquid-92.1 ± 0.3kcal/molCcbPihlaja and Heikkila, 1967ALS
Deltafliquid-90.01 ± 0.20kcal/molCcbSnelson and Skinner, 1961ALS
Quantity Value Units Method Reference Comment
Deltacliquid-558. ± 3.kcal/molAVGN/AAverage of 6 values; Individual data points

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
34.39298.Conti, Gianni, et al., 1976DH

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
Tboil378.7KN/AAldrich Chemical Company Inc., 1990BS
Quantity Value Units Method Reference Comment
Deltavap8.9 ± 0.9kcal/molAVGN/AAverage of 6 values; Individual data points

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
378.20.993Weast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
9.4293.VSkuratov, Strepikheev, et al., 1957combustion 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

21,3-Dioxane = 1,3,7,9 Tetraoxacyclododecane

By formula: 2C4H8O2 = C8H16O4

Quantity Value Units Method Reference Comment
Deltar-2.4 ± 0.67kcal/molEqkSzymanski, 1991solid 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)197.3kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity190.3kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
10.33EICollin and Conde, 1966RDSH
10.12PEAsfandiarov and Zykov, 1983Vertical value; LBLHLM
10.12PEKobayashi and Nagakura, 1973Vertical value; LLK
10.1PESweigart and Turner, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH2O+11.82?EICollin and Conde, 1966RDSH
C2H4+13.16?EICollin and Conde, 1966RDSH
C3H5O+12.17?EICollin and Conde, 1966RDSH
C3H6O+11.12CH2OEICollin and Conde, 1966RDSH
C3H7O+12.17CHOEICollin and Conde, 1966RDSH
C4H7O2+10.42HEICollin and Conde, 1966RDSH

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)

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

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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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

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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), 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]


Notes

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), References