1,2,4-Trioxolane

Formula: C₂H₄O₃
Molecular weight: 76.0514
IUPAC Standard InChI: InChI=1S/C2H4O3/c1-3-2-5-4-1/h1-2H2
IUPAC Standard InChIKey: RZYIPLSVRHWROD-UHFFFAOYSA-N
CAS Registry Number: 289-14-5
Chemical structure:
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Gas phase thermochemistry data

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Data compiled by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
8.196	50.	Dorofeeva O.V., 1992	p=1 bar. Selected Cp(T) values are in good agreement with those calculated by [ Kuhne H., 1976], while S(T) values are about 6 J/mol*K larger. This discrepancy is due to taking into account of optical isomers for C2 conformation by [ Dorofeeva O.V., 1992].
9.379	100.
10.60	150.
12.15	200.
15.25	273.15
16.46 ± 0.96	298.15
16.55	300.
21.44	400.
25.772	500.
29.314	600.
32.189	700.
34.543	800.
36.494	900.
38.124	1000.
39.498	1100.
40.662	1200.
41.656	1300.
42.505	1400.
43.236	1500.

Phase change data

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Data compiled by: William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
8.32	281.	A	Stephenson and Malanowski, 1987	Based on data from 273. to 289. K. See also Garvin and Schubert S.J., 1956.

Gas phase ion energetics data

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Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV)	Method	Reference	Comment
10.1	PE	Brown and Marcinko, 1978	LLK
10.67 ± 0.03	PE	Brown and Marcinko, 1978	Vertical value; LLK

Vibrational and/or electronic energy levels

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Data compiled by: Marilyn E. Jacox

State: X

Vib. sym.	No.	Approximate type of mode	cm^-1		Med.	Method	References


a	1	CH stretch	2973	m	Ar	IR	Kuhne and Gunthard, 1976 Hawkins, Kohlmiller, et al., 1982
	2	CH stretch	2900	m	Ar	IR	Kuhne and Gunthard, 1976 Hawkins, Kohlmiller, et al., 1982
	4	CH₂ bend	1387	m	Ar	IR	Kuhne and Gunthard, 1976 Hawkins, Kohlmiller, et al., 1982
	5		1202	m	Ar	IR	Kuhne and Gunthard, 1976 Hawkins, Kohlmiller, et al., 1982
	6		1143	w	Ar	IR	Kuhne and Gunthard, 1976
	7	C-Op stretch	1037.01		gas	IR	Sablinskas, Hegelund, et al., 2005
	7	C-Op stretch	1029	s	Ar	IR	Kuhne and Gunthard, 1976 Kohlmiller and Andrews, 1981 Hawkins, Kohlmiller, et al., 1982
	7	C-Op stretch	1021		Xe	IR	Kohlmiller and Andrews, 1981
	8	COC s-stretch	956.07		gas	IR	Niki, Maker, et al., 1981 Sablinskas, Hegelund, et al., 2005
	8	COC s-stretch	952	vs	Ar	IR	Kuhne and Gunthard, 1976 Kohlmiller and Andrews, 1981 Hawkins, Kohlmiller, et al., 1982
	8	COC s-stretch	945		Xe	IR	Kohlmiller and Andrews, 1981
	9	O-O stretch	810	w	gas	IR	Niki, Maker, et al., 1981
	9	O-O stretch	808	s	Ar	IR	Kuhne and Gunthard, 1976 Kohlmiller and Andrews, 1981 Hawkins, Kohlmiller, et al., 1982
	9	O-O stretch	802		Xe	IR	Kohlmiller and Andrews, 1981
	10	Ring bend	737	w	Ar	IR	Kuhne and Gunthard, 1976 Hawkins, Kohlmiller, et al., 1982
	11	Ring pucker	352	w	Ar	IR	Kuhne and Gunthard, 1976
b	12	CH stretch	2967	s	Ar	IR	Kuhne and Gunthard, 1976 Hawkins, Kohlmiller, et al., 1982
	13	CH stretch	2894	m	Ar	IR	Kuhne and Gunthard, 1976 Hawkins, Kohlmiller, et al., 1982
	14		1483	w	Ar	IR	Kuhne and Gunthard, 1976
	15	Mixed	1346	m	Ar	IR	Kuhne and Gunthard, 1976 Hawkins, Kohlmiller, et al., 1982
	16		1196	m	Ar	IR	Kuhne and Gunthard, 1976 Hawkins, Kohlmiller, et al., 1982
	17	Mixed	1129	s	Ar	IR	Kuhne and Gunthard, 1976 Kohlmiller and Andrews, 1981 Hawkins, Kohlmiller, et al., 1982
	17	Mixed	1130		Xe	IR	Kohlmiller and Andrews, 1981
	18	COC a-stretch	1082.12		gas	IR	Niki, Maker, et al., 1981 Sablinskas, Hegelund, et al., 2005
	18	COC a-stretch	1078	vs	Ar	IR	Kuhne and Gunthard, 1976 Kohlmiller and Andrews, 1981 Hawkins, Kohlmiller, et al., 1982
	18	COC a-stretch	1072		Xe	IR	Kohlmiller and Andrews, 1981
	19	C-Op stretch	926	w	Ar	IR	Kuhne and Gunthard, 1976 Hawkins, Kohlmiller, et al., 1982
	20	Ring bend	698	m	Ar	IR	Kuhne and Gunthard, 1976 Hawkins, Kohlmiller, et al., 1982
	21		193	m	Ar	IR	Kuhne and Gunthard, 1976

Additional references: Jacox, 1994, page 422; Jacox, 1998, page 367; Gillies and Kuczkowski, 1972; Kuczkowski, Gillies, et al., 1976; Mazur and Kuczkowski, 1977; Samuni and Haas, 1996

Notes

Weak

Medium

Strong

Very strong

References

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

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]

Kuhne H., 1976
Kuhne H., Spectroscopic study of the ozone-ethylene reaction. Matrix-infrared spectra of three isotopic ethylene ozonides., J. Phys. Chem., 1976, 80, 1238-1247. [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]

Garvin and Schubert S.J., 1956
Garvin, David; Schubert S.J., The Vapor Phase Infrared Spectra Of The Ozonides Of Ethylene, Propylene And Isobutylent, J. Phys. Chem., 1956, 60, 6, 807-808, https://doi.org/10.1021/j150540a030 . [all data]

Brown and Marcinko, 1978
Brown, R.S.; Marcinko, R.W., Photoelectron spectra of the ozonides of ethylene, cyclopentene, and cyclohexene. Experimental evidence for the magnitude of the "pure" inductive effect of an ether oxygen on ionization energy, J. Am. Chem. Soc., 1978, 100, 5584. [all data]

Kuhne and Gunthard, 1976
Kuhne, H.; Gunthard, H.H., Spectroscopic study of the ozone-ethylene reaction. Matrix-infrared spectra of three isotopic ethylene ozonides, J. Phys. Chem., 1976, 80, 11, 1238, https://doi.org/10.1021/j100552a025 . [all data]

Hawkins, Kohlmiller, et al., 1982
Hawkins, M.; Kohlmiller, C.K.; Andrews, L., Matrix infrared spectra and photolysis and pyrolysis of isotopic secondary ozonides of ethylene, J. Phys. Chem., 1982, 86, 16, 3154, https://doi.org/10.1021/j100213a019 . [all data]

Sablinskas, Hegelund, et al., 2005
Sablinskas, V.; Hegelund, F.; Ceponkus, J.; Bariseviciute, R.; Aleksa, V.; Nelander, B., A High-Resolution FT-IR Study of the Fundamental Bands ν, J. Phys. Chem. A, 2005, 109, 39, 8719, https://doi.org/10.1021/jp051647e . [all data]

Kohlmiller and Andrews, 1981
Kohlmiller, C.K.; Andrews, L., Infrared spectrum of the primary ozonide of ethylene in solid xenon, J. Am. Chem. Soc., 1981, 103, 10, 2578, https://doi.org/10.1021/ja00400a016 . [all data]

Niki, Maker, et al., 1981
Niki, H.; Maker, P.D.; Savage, C.M.; Breitenbach, L.P., A FT IR study of a transitory product in the gas-phase ozone-ethylene reaction, J. Phys. Chem., 1981, 85, 8, 1024, https://doi.org/10.1021/j150608a020 . [all data]

Jacox, 1994
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules, American Chemical Society, Washington, DC, 1994, 464. [all data]

Jacox, 1998
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules: supplement A, J. Phys. Chem. Ref. Data, 1998, 27, 2, 115-393, https://doi.org/10.1063/1.556017 . [all data]

Gillies and Kuczkowski, 1972
Gillies, C.W.; Kuczkowski, R.L., J. Am. Chem. Soc., 1972, 94, 6337, 7609. [all data]

Kuczkowski, Gillies, et al., 1976
Kuczkowski, R.L.; Gillies, C.W.; Gallaher, K.L., Microwave spectrum and structure of ethylene ozonide: Effects of large axes rotations in structure calculations, J. Mol. Spectrosc., 1976, 60, 1-3, 361, https://doi.org/10.1016/0022-2852(76)90139-9 . [all data]

Mazur and Kuczkowski, 1977
Mazur, U.; Kuczkowski, R.L., Microwave spectrum and structure of ethylene ozonide-D4, J. Mol. Spectrosc., 1977, 65, 1, 84, https://doi.org/10.1016/0022-2852(77)90360-5 . [all data]

Samuni and Haas, 1996
Samuni, U.; Haas, Y., An ab-initio study of the normal modes of the primary and secondary ozonides of ethylene, Spectrochim. Acta A, 1996, 52, 11, 1479, https://doi.org/10.1016/0584-8539(96)01706-0 . [all data]

Notes

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Symbols used in this document:

C_p,gas Constant pressure heat capacity of gas

Δ_vapH Enthalpy of vaporization
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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C_p,gas	Constant pressure heat capacity of gas
Δ_vapH	Enthalpy of vaporization