Pentalene, octahydro-, cis-
- Formula: C8H14
- Molecular weight: 110.1968
- IUPAC Standard InChIKey: AEBWATHAIVJLTA-OCAPTIKFSA-N
- CAS Registry Number: 1755-05-1
- 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. - Stereoisomers:
- Other names: cis-Bicyclo[3.3.0]octane; cis-Octahydropentalene; Bicyclo[3.3.0]octane (cis); Octahydropentalene, (Z)-; (Z)-Bicyclo[3.3.0]octane; Bicyclo[3.3.0]octane
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Condensed phase thermochemistry data
Go To: Top, Phase change data, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -32.6 ± 0.3 | kcal/mol | Ccb | Chang, McNally, et al., 1970 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1198.1 ± 0.3 | kcal/mol | Ccb | Chang, McNally, et al., 1970 | Corresponding ΔfHºliquid = -32.5 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1198.86 ± 0.66 | kcal/mol | Ccb | Barrett and Linstead, 1936 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1197.7 ± 2.3 kcal/mol; Corresponding ΔfHºliquid = -31.75 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1187.4 ± 0.3 | kcal/mol | Ccb | Barrett and Linstead, 1935 | Corresponding ΔfHºliquid = -43.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
50.76 | 308. | Chang, McNally, et al., 1970 | T = 308, 334 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, 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:
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 410.28 | K | N/A | Mair, Eberly, et al., 1958 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tboil | 408. | K | N/A | Desty and Whyman, 1957 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 409. | K | N/A | Roberts and Gorham, 1952 | Uncertainty assigned by TRC = 3. K; TRC |
Tboil | 409.4 | K | N/A | Cope and Schmitz, 1950 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 409. | K | N/A | Barrett and Linstead, 1936, 2 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 223.82 | K | N/A | Mair, Eberly, et al., 1958 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 224. | K | N/A | Rytina, Schiessler, et al., 1949 | Uncertainty assigned by TRC = 8. K; TRC |
Tfus | 224. | K | N/A | Anonymous, 1948 | Uncertainty assigned by TRC = 8. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 10.3 ± 0.2 | kcal/mol | V | Chang, McNally, et al., 1970 | ALS |
ΔvapH° | 10.3 | kcal/mol | N/A | Chang, McNally, et al., 1970 | DRB |
ΔvapH° | 10.3 ± 0.2 | kcal/mol | N/A | Chang, McNally, et al., 1970 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.0 | 308. | A | Stephenson and Malanowski, 1987 | Based on data from 298. to 318. K.; AC |
9.92 ± 0.1 | 318. | N/A | Chang, McNally, et al., 1970 | AC |
Mass spectrum (electron ionization)
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: 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. |
---|---|
NIST MS number | 20124 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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.
Chang, McNally, et al., 1970
Chang, Sho-ju.; McNally, D.; Shary-Tehrany, S.; Hickey, S.M.J.; Boyd, R.H.,
The heats of combustion and strain energies of bicylo[n.m.O]alkanes,
J. Am. Chem. Soc., 1970, 92, 3109-3118. [all data]
Barrett and Linstead, 1936
Barrett, J.W.; Linstead, R.P.,
Fused carbon rings. Part X. Some fundamental properties of the 0:3:3-bicycloOctane ring,
J. Chem. Soc., 1936, 611-616. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Barrett and Linstead, 1935
Barrett, J.W.; Linstead, R.P.,
Fused carbon rings. Part IV. Further investigation of 0:3:3-bicycloOctanones in relation to the strain theory,
J. Chem. Soc., 1935, 436-442. [all data]
Mair, Eberly, et al., 1958
Mair, B.J.; Eberly; Krouskop, N.C.; Rossini, F.D.,
Anal. Chem., 1958, 30, 393. [all data]
Desty and Whyman, 1957
Desty, D.H.; Whyman, B.H.F.,
Anal. Chem., 1957, 29, 320. [all data]
Roberts and Gorham, 1952
Roberts, J.D.; Gorham, W.F.,
Syntheses of Some Bicyclo[3.3.0]octane Derivatives,
J. Am. Chem. Soc., 1952, 74, 2278. [all data]
Cope and Schmitz, 1950
Cope, A.C.; Schmitz, W.R.,
Cyclic Polyolefins VII. Structure of the Eight-membered Cyclic Dimer of Chloroprene,
J. Am. Chem. Soc., 1950, 72, 3056. [all data]
Barrett and Linstead, 1936, 2
Barrett, J.W.; Linstead, R.P.,
J. Chem. Soc., 1936, 1936, 611. [all data]
Rytina, Schiessler, et al., 1949
Rytina, A.W.; Schiessler, R.W.; Whitmore, F.C.,
The Preparation and Properties of cis-(0.3.3)-Bicyclooctane,
J. Am. Chem. Soc., 1949, 71, 751-2. [all data]
Anonymous, 1948
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 6, Natl. Bur. Stand., 1948. [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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid 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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