7-Oxabicyclo[4.1.0]heptane
- Formula: C6H10O
- Molecular weight: 98.1430
- IUPAC Standard InChI: InChI=1S/C6H10O/c1-2-4-6-5(3-1)7-6/h5-6H,1-4H2
- IUPAC Standard InChIKey: ZWAJLVLEBYIOTI-UHFFFAOYSA-N
- CAS Registry Number: 286-20-4
- 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: Cyclohexane, 1,2-epoxy-; Cyclohexene epoxide; Cyclohexene oxide; Cyclohexene 1-oxide; Cyclohexylene oxide; Tetramethyleneoxirane; 1,2-Cyclohexene oxide; 1,2-Epoxycyclohexane; Bicyclo[4.1.0]heptane, 7-oxa-; CCHO; NSC 128074
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -125.5 ± 1.1 | kJ/mol | Ccb | Kozina, Timofeeva, et al., 1988 | See Timofeeva, Lukyanova, et al., 1984 |
| ΔfH°gas | -122.2 ± 2.2 | kJ/mol | Ccb | Andruzzi, Li, et al., 1987 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change 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 | -166.0 ± 1.1 | kJ/mol | Ccb | Kozina, Timofeeva, et al., 1988 | See Timofeeva, Lukyanova, et al., 1984; ALS |
| ΔfH°liquid | -165.3 ± 1.0 | kJ/mol | Ccb | Andruzzi, Li, et al., 1987 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -3624.2 ± 1.0 | kJ/mol | Ccb | Kozina, Timofeeva, et al., 1988 | See Timofeeva, Lukyanova, et al., 1984; Corresponding ΔfHºliquid = -166.0 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -3624.9 ± 0.6 | kJ/mol | Ccb | Andruzzi, Li, et al., 1987 | Corresponding ΔfHºliquid = -165.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 221.98 | J/mol*K | N/A | Nakamura, Suga, et al., 1980 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 166.12 | 300. | Nakamura, Suga, et al., 1980 | T = 13 to 300 K. Unsmoothed experimental datum for Cp at 296.96 K is 164.98 J/mol*K.; 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
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
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 402.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
| Tboil | 404.7 | K | N/A | Weast and Grasselli, 1989 | BS |
| Tboil | 402. to 403. | K | N/A | Frinton Laboratories Inc., 1986 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| Ttriple | 238.14 | K | N/A | Nakamura, Suga, et al., 1980, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 40.5 ± 0.2 | kJ/mol | C | Kozina, Timofeeva, et al., 1988 | See Timofeeva, Lukyanova, et al., 1984; ALS |
| ΔvapH° | 40.5 | kJ/mol | N/A | Kozina, Timofeeva, et al., 1988 | DRB |
| ΔvapH° | 43.2 ± 2.0 | kJ/mol | E | Andruzzi, Li, et al., 1987 | ALS |
| ΔvapH° | 43.1 | kJ/mol | N/A | Andruzzi, Li, et al., 1987 | DRB |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 1.06 | 238.1 | Nakamura, Suga, et al., 1980 | Based on data from 10. to 300. K.; AC |
Entropy of fusion
| ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 49.38 | 193.1 | Nakamura, Suga, et al., 1980, 2 | CAL |
| 4.47 | 238.1 |
Enthalpy of phase transition
| ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 9.5351 | 193.10 | crystaline, II | crystaline, I | Nakamura, Suga, et al., 1980 | DH |
| 1.0645 | 238.14 | crystaline, I | liquid | Nakamura, Suga, et al., 1980 | DH |
Entropy of phase transition
| ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 49.39 | 193.10 | crystaline, II | crystaline, I | Nakamura, Suga, et al., 1980 | DH |
| 4.470 | 238.14 | crystaline, I | liquid | Nakamura, Suga, et al., 1980 | DH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Kozina, Timofeeva, et al., 1988
Kozina, M.P.; Timofeeva, L.P.; Luk'Yanova, V.A.; Pimenova, S.M.; Kas'yan, L.I.,
Enthalpies of formation and some alicyclic epoxy compounds,
Russ. J. Phys. Chem. (Engl. Transl.), 1988, 62, 609-612. [all data]
Timofeeva, Lukyanova, et al., 1984
Timofeeva, L.P.; Lukyanova, V.A.; Kozina, M.P.; Stepanova, N.V.,
Enthalpies of combustion and formation of some epoxides of cyclic alkenes,
Probl. Kalorim. Khim. Termodin., Dokl. Vses. Konf., 10th, 1984, 1, 193-195. [all data]
Andruzzi, Li, et al., 1987
Andruzzi, F.; Li, S.; Pilcher, G.; Heatley, F.,
Enthalpy of polymerisation of 7-oxabicyclo[4.1.0]heptane,
Makromol. Chem., 1987, 188, 2643-2650. [all data]
Nakamura, Suga, et al., 1980
Nakamura, N.; Suga, H.; Seki, S.,
Calorimetric study on orientationally disordered crystals. Cyclohexene oxide and cyclohexanone,
Bull. Chem. Soc. Japan, 1980, 53(10), 2755-2761. [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]
Frinton Laboratories Inc., 1986
Frinton Laboratories Inc.,
Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [all data]
Nakamura, Suga, et al., 1980, 2
Nakamura, N.; Suga, H.; Seki, S.,
Calorimetric study on orientationally disordered crystals. Cyclohexene oxide and cyclohexanone.,
Bull. Chem. Soc. Japan, 1980, 53, 10, 2755, https://doi.org/10.1246/bcsj.53.2755
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition 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 ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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