Spiropentane
- Formula: C5H8
- Molecular weight: 68.1170
- IUPAC Standard InChIKey: OGNAOIGAPPSUMG-UHFFFAOYSA-N
- CAS Registry Number: 157-40-4
- 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: Spiro[2.2]pentane
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics 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: Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
S°liquid | 193.68 | J/mol*K | N/A | Scott, Finke, et al., 1950 |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
134.52 | 298.15 | Scott, Finke, et al., 1950 | T = 12 to 312 K. |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics 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
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 312.1 | K | N/A | Majer and Svoboda, 1985 | |
Tboil | 303.18 | K | N/A | Cleaves and Sherrick, 1946 | Uncertainty assigned by TRC = 0.1 K; same as in 1946 sla 1; TRC |
Tboil | 312.18 | K | N/A | Slabey, 1946 | Uncertainty assigned by TRC = 0.1 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 166.10 | K | N/A | Cleaves and Sherrick, 1946 | Uncertainty assigned by TRC = 0.1 K; same as in 1946 sla 1; TRC |
Tfus | 166.10 | K | N/A | Slabey, 1946 | Uncertainty assigned by TRC = 0.1 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 166.14 | K | N/A | Scott, Finke, et al., 1950, 2 | Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 506.4 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 27.7 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 27.5 ± 0.1 | kJ/mol | C | Scott, Finke, et al., 1950 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
26.76 | 312.1 | N/A | Majer and Svoboda, 1985 | |
26.748 | 312.13 | N/A | Scott, Finke, et al., 1950 | P = 101.325 kPa; DH |
28.6 | 291. | A | Stephenson and Malanowski, 1987 | Based on data from 276. to 344. K. See also Scott, Finke, et al., 1950, 3.; AC |
28.3 ± 0.1 | 283. | C | Scott, Finke, et al., 1950 | AC |
26.7 ± 0.1 | 312. | C | Scott, Finke, et al., 1950 | AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kJ/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
283. to 312. | 41.44 | 0.2778 | 506.4 | Majer and Svoboda, 1985 |
Entropy of vaporization
ΔvapS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
85.70 | 312.13 | Scott, Finke, et al., 1950 | P; DH |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
276.78 to 343.98 | 4.04134 | 1089.801 | -42.079 | Scott, Finke, et al., 1950 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
6.4333 | 166.14 | Scott, Finke, et al., 1950 | DH |
6.43 | 166.1 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
38.72 | 166.14 | Scott, Finke, et al., 1950 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, 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 evaluated as indicated in comments:
L - 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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C5H8+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.26 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.26 | PE | Gleiter, Krennrich, et al., 1986 | LBLHLM |
9.26 | EI | Lossing and Traeger, 1975 | LLK |
9.26 | EI | Holmes, 1974 | LLK |
9.37 ± 0.05 | EI | Puttemans and Delvaux, 1973 | LLK |
9.73 | PE | Gleiter, Krennrich, et al., 1986 | Vertical value; LBLHLM |
9.45 | PE | Dewar and Worley, 1969 | Vertical value; RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H3+ | 13.46 ± 0.15 | C2H4+H | EI | Puttemans and Delvaux, 1973 | LLK |
C3H4+ | 11.17 ± 0.08 | C2H4 | EI | Puttemans and Delvaux, 1973 | LLK |
C4H5+ | 10.20 | CH3 | EI | Holmes, 1974 | LLK |
C4H5+ | 10.65 ± 0.08 | CH3 | EI | Puttemans and Delvaux, 1973 | LLK |
C5H7+ | 9.26 | H | EI | Lossing and Traeger, 1975, 2 | LLK |
C5H7+ | 9.53 | H | EI | Lossing and Traeger, 1975 | LLK |
C5H7+ | 9.53 ± 0.03 | H | EI | Holmes, 1974 | LLK |
C5H7+ | 9.93 ± 0.10 | H | EI | Puttemans and Delvaux, 1973 | LLK |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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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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. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118856 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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.
Scott, Finke, et al., 1950
Scott, D.W.; Finke, H.L.; Hubbard, W.N.; McCullough, J.P.; Gross, M.E.; Williamson, K.D.; Waddington, G.; Huffman, H.M.,
Spiropentane: heat capacity, heats of fusion and vaporization, vapor pressure, entropy and thermodynamic functions,
J. Am. Chem. Soc., 1950, 72, 4664-4668. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Cleaves and Sherrick, 1946
Cleaves, A.P.; Sherrick, M.E.,
, Natl. Advis. Comm. Aeronaut., 1946. [all data]
Slabey, 1946
Slabey, V.A.,
, Natl. Advis. Comm. Aeronaut., 1946. [all data]
Scott, Finke, et al., 1950, 2
Scott, D.W.; Finke, H.L.; Hubbard, W.N.; McCullough, J.P.; Gross, M.E.; Williamson, K.D.; Waddington, G.; Huffman, H.M.,
Spiropentane: Heat Capacity, Heats of Fusion and Vaporization, Vapor Pressure, Entropy and Thermodynamic Functions,
J. Am. Chem. Soc. 72, 1950, 4664 1950. [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]
Scott, Finke, et al., 1950, 3
Scott, D.W.; Finke, H.L.; Gross, M.E.; Guthrie, G.B.; Huffman, H.M.,
2,3-Dithiabutane: low temperature heat capacity, heat of fusion, heat of vaporization, vapor pressure, entropy and thermodynamic functions,
J. Am. Chem. Soc., 1950, 72, 2424-2430. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Gleiter, Krennrich, et al., 1986
Gleiter, R.; Krennrich, G.; Brinker, U.H.,
Electronic structure of spiropentane and some derivatives,
J. Org. Chem., 1986, 51, 2899. [all data]
Lossing and Traeger, 1975
Lossing, F.P.; Traeger, J.C.,
Stabilization in cyclopentadienyl, cyclopentenyl, and cyclopentyl cations,
J. Am. Chem. Soc., 1975, 97, 1579. [all data]
Holmes, 1974
Holmes, J.L.,
The mass spectra of isomeric hydrocarbons - II: The C5H8 isomers, spiropentane, cyclopentene, 1,3-pentadiene and isoprene; the mechanisms and energetics of their fragmentations,
Org. Mass Spectrom., 1974, 8, 247. [all data]
Puttemans and Delvaux, 1973
Puttemans, J.-P.; Delvaux, J.C.,
Ionisation et fragmentation d'isomeres C5H8 sous impact electronique. Spiropentane - methylenecyclobutane - isoprene,
Ing. Chim. Brussell, 1973, 55(267-8), 7. [all data]
Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation,
J. Chem. Phys., 1969, 50, 654. [all data]
Lossing and Traeger, 1975, 2
Lossing, F.P.; Traeger, J.C.,
Free radicals by mass spectrometry XLVI. Heats of formation of C5H7 and C5H9 radicals and cations.,
J. Am. Chem. Soc., 1975, 19, 9. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ΔvapS Entropy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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