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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -93. ± 2. | kJ/mol | Ccb | Chang, McNally, et al., 1970 | ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
129.91 | 298.15 | Chang S., 1970 | These values were calculated by a method of force field; their uncertainties may exceed 5-10 J/mol*K.; GT |
184.14 | 400. | ||
233.17 | 500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, 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 | -136. ± 1. | kJ/mol | Ccb | Chang, McNally, et al., 1970 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -5013. ± 1. | kJ/mol | Ccb | Chang, McNally, et al., 1970 | Corresponding ΔfHºliquid = -136. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -5016.0 ± 2.8 | kJ/mol | Ccb | Barrett and Linstead, 1936 | Reanalyzed by Cox and Pilcher, 1970, Original value = -5011.2 ± 9.6 kJ/mol; Corresponding ΔfHºliquid = -132.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -4968. ± 1. | kJ/mol | Ccb | Barrett and Linstead, 1935 | Corresponding ΔfHºliquid = -181. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
212.4 | 308. | Chang, McNally, et al., 1970 | T = 308, 334 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, 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° | 43.1 ± 0.8 | kJ/mol | V | Chang, McNally, et al., 1970 | ALS |
ΔvapH° | 43.0 | kJ/mol | N/A | Chang, McNally, et al., 1970 | DRB |
ΔvapH° | 43.1 ± 0.8 | kJ/mol | N/A | Chang, McNally, et al., 1970 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
42.0 | 308. | A | Stephenson and Malanowski, 1987 | Based on data from 298. to 318. K.; AC |
41.5 ± 0.4 | 318. | N/A | Chang, McNally, et al., 1970 | AC |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, 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
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
By formula: 2H2 + C8H10 = C8H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -227. ± 2. | kJ/mol | Chyd | Rogers, Loggins, et al., 1990 | liquid phase; solvent: Hexane |
By formula: 2H2 + C8H10 = C8H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -227. ± 2. | kJ/mol | Chyd | Rogers, Loggins, et al., 1990 | liquid phase; solvent: Hexane |
By formula: H2 + C8H12 = C8H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -112. ± 1. | kJ/mol | Chyd | Rogers, Loggins, et al., 1990 | liquid phase; solvent: Hexane |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, 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
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Squalane | 50. | 859.9 | Lunskii and Paizanskaya, 1988 | He; Column length: 50. m; Column diameter: 0.22 mm |
Capillary | Squalane | 70. | 865.2 | Lunskii and Paizanskaya, 1988 | He; Column length: 50. m; Column diameter: 0.22 mm |
Capillary | Squalane | 90. | 870. | Engewald, Epsch, et al., 1976 | N2; Column length: 100. m; Column diameter: 0.23 mm |
Capillary | Vacuum Grease Oil (VM-4) | 35. | 858. | Sidorov, Petrova, et al., 1972 | |
Capillary | Vacuum Grease Oil (VM-4) | 45. | 863. | Sidorov, Petrova, et al., 1972 | |
Capillary | Vacuum Grease Oil (VM-4) | 50. | 865. | Sidorov, Petrova, et al., 1972 | |
Capillary | Vacuum Grease Oil (VM-4) | 58. | 869. | Sidorov, Petrova, et al., 1972 | |
Capillary | Vacuum Grease Oil (VM-4) | 68. | 874. | Sidorov, Petrova, et al., 1972 | |
Packed | Vacuum Grease Oil (VM-4) | 35. | 858. | Sidorov, Ivanova, et al., 1971 | |
Capillary | Squalane | 70. | 870. | Schomburg, 1966 | |
Capillary | Squalane | 70. | 870. | Schomburg, 1966 | |
Packed | Squalane | 150. | 891. | Schomburg, 1964 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, 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]
Chang S., 1970
Chang S.,
The heats of combustion and strain energies of bicyclo[n.m.0]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]
Rogers, Loggins, et al., 1990
Rogers, D.W.; Loggins, S.A.; Samuel, S.D.; Finnerty, M.A.; Liebman, J.F.,
Homoaromaticity and homoconjugation in the quinacenes: biquinacene, triquinacene, and hexaquinacene,
Struct. Chem., 1990, 1, 481-489. [all data]
Lunskii and Paizanskaya, 1988
Lunskii, M.Kh.; Paizanskaya, I.L.,
Identification of hydrocarbons C1-C9 of petrol fractions of oils and condensates in the use of capillary columns with dinonylphthalate,
Zh. Anal. Khim., 1988, 43, 127-135. [all data]
Engewald, Epsch, et al., 1976
Engewald, W.; Epsch, K.; Welsch, Th.; Graefe, J.,
Molekülstruktur und Retentionsverhalten. VI. Retentionsverhalten von bicycle[n.m.0]alkanen bei der gas-adsorptions- und gas-verteilungs-chromatographie,
J. Chromatogr., 1976, 119, 119-128, https://doi.org/10.1016/S0021-9673(00)86776-X
. [all data]
Sidorov, Petrova, et al., 1972
Sidorov, R.I.; Petrova, V.I.; Ivanova, M.P.,
Qualitative analysis of wide-boiling fraction C5-C10 with capillary chromatography
in Processes in chromatographic columns. Vol.17, 1972, 14-25. [all data]
Sidorov, Ivanova, et al., 1971
Sidorov, R.I.; Ivanova, M.P.; Petrova, V.I.,
Temperature dependence of cycloalkane's retention and its using in identification of structure,
Gazovaya Khromatografiya, 1971, 15, 18-26. [all data]
Schomburg, 1966
Schomburg, G.,
Gaschromatographische Retentionsdaten und struktur chemischer verbindungen. III. Alkylverzweigte und ungesättigte cyclische Kohlenwasserstoffe,
J. Chromatogr., 1966, 23, 18-41, https://doi.org/10.1016/S0021-9673(01)98653-4
. [all data]
Schomburg, 1964
Schomburg, G.,
Gas-Chromatographische Retentionsdaten und Struktur Chemischer Verbindungen. I. Verzweigte Aliphatische und Alicyclische Carbonsäure-Methylester,
J. Chromatogr., 1964, 14, 157-177, https://doi.org/10.1016/S0021-9673(00)86608-X
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas 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°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.