7-Oxabicyclo[4.1.0]heptane
- Formula: C6H10O
- Molecular weight: 98.1430
- 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, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -30.00 ± 0.26 | kcal/mol | Ccb | Kozina, Timofeeva, et al., 1988 | See Timofeeva, Lukyanova, et al., 1984 |
ΔfH°gas | -29.21 ± 0.53 | kcal/mol | Ccb | Andruzzi, Li, et al., 1987 |
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 | -39.67 ± 0.26 | kcal/mol | Ccb | Kozina, Timofeeva, et al., 1988 | See Timofeeva, Lukyanova, et al., 1984; ALS |
ΔfH°liquid | -39.51 ± 0.24 | kcal/mol | Ccb | Andruzzi, Li, et al., 1987 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -866.20 ± 0.24 | kcal/mol | Ccb | Kozina, Timofeeva, et al., 1988 | See Timofeeva, Lukyanova, et al., 1984; Corresponding ΔfHºliquid = -39.67 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -866.4 ± 0.1 | kcal/mol | Ccb | Andruzzi, Li, et al., 1987 | Corresponding ΔfHºliquid = -39.51 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 53.054 | cal/mol*K | N/A | Nakamura, Suga, et al., 1980 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
39.704 | 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° | 9.68 ± 0.05 | kcal/mol | C | Kozina, Timofeeva, et al., 1988 | See Timofeeva, Lukyanova, et al., 1984; ALS |
ΔvapH° | 9.68 | kcal/mol | N/A | Kozina, Timofeeva, et al., 1988 | DRB |
ΔvapH° | 10.3 ± 0.48 | kcal/mol | E | Andruzzi, Li, et al., 1987 | ALS |
ΔvapH° | 10.3 | kcal/mol | N/A | Andruzzi, Li, et al., 1987 | DRB |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
0.253 | 238.1 | Nakamura, Suga, et al., 1980 | Based on data from 10. to 300. K.; AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.80 | 193.1 | Nakamura, Suga, et al., 1980, 2 | CAL |
1.07 | 238.1 |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
2.2789 | 193.10 | crystaline, II | crystaline, I | Nakamura, Suga, et al., 1980 | DH |
0.25442 | 238.14 | crystaline, I | liquid | Nakamura, Suga, et al., 1980 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
11.80 | 193.10 | crystaline, II | crystaline, I | Nakamura, Suga, et al., 1980 | DH |
1.068 | 238.14 | crystaline, I | liquid | Nakamura, Suga, et al., 1980 | DH |
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
View reactions leading to C6H10O+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 202.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 194.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.82 | EI | Alai and Rye, 1984 | LBLHLM |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H7O+ | 9.90 | CH3 | EI | Alai and Rye, 1984 | LBLHLM |
IR Spectrum
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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
Gas Phase Spectrum
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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center |
State | gas |
Instrument | HP-GC/MS/IRD |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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]
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]
Alai and Rye, 1984
Alai, M.; Rye, R.T.B.,
Fragmentation of selected C6H10O isomers: Evidence for a common [C5H7O]+ ion generated by methyl loss from cyclohexene oxide and 5,6-dihydro-4-methyl-2H-pyran,
Org. Mass Spectrom., 1984, 19, 506. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
AE Appearance energy 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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