1,1'-Bicyclopentyl
- Formula: C10H18
- Molecular weight: 138.2499
- IUPAC Standard InChIKey: MAWOHFOSAIXURX-UHFFFAOYSA-N
- CAS Registry Number: 1636-39-1
- 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. - Other names: Bicyclopentyl; Cyclopentane, cyclopentyl-; Cyclopentylcyclopentane; Dicyclopentyl
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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 | -179.3 ± 1.0 | kJ/mol | Ccb | Good and Lee, 1976 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -6328.26 ± 0.84 | kJ/mol | Ccb | Good and Lee, 1976 | Corresponding ΔfHºliquid = -179.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -6205.8 | kJ/mol | Ccb | Gollis, Belenyessy, et al., 1962 | Corresponding ΔfHºliquid = -301.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -6332. ± 3. | kJ/mol | Ccb | Kozina, Skuratov, et al., 1961 | Corresponding ΔfHºliquid = -175. 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 |
---|---|---|---|
238.9 | 298.15 | Good and Lee, 1976 | DH |
229.7 | 311. | Gollis, Belenyessy, et al., 1962, 2 | Temperatures 100, 200, 300°F.; 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 463. | K | N/A | Kharasch, Hancock, et al., 1956 | Uncertainty assigned by TRC = 3. K; TRC |
Tboil | 462. | K | N/A | McBee, Roberts, et al., 1955 | Uncertainty assigned by TRC = 3. K; TRC |
Tboil | 463.6 | K | N/A | Boord, Greenlee, et al., 1950 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tboil | 463.59 | K | N/A | Boord, Greenlee, et al., 1949 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tboil | 463.60 | K | N/A | Anonymous, 1948 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 238. ± 1. | K | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 50.4 ± 0.1 | kJ/mol | EB | Chirico and Steele, 2005 | Based on data from 383. to 509. K.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
44.1 ± 0.1 | 400. | EB | Chirico and Steele, 2004 | Based on data from 384. to 509. K.; AC |
41.6 ± 0.1 | 440. | EB | Chirico and Steele, 2004 | Based on data from 384. to 509. K.; AC |
38.9 ± 0.2 | 480. | EB | Chirico and Steele, 2004 | Based on data from 384. to 509. K.; AC |
43.2 | 365. | A | Stephenson and Malanowski, 1987 | Based on data from 350. to 393. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
13.4 | 237.8 | Chirico and Steele, 2004 | AC |
Reaction 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 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
3 + C10H12 =
By formula: 3H2 + C10H12 = C10H18
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -295. ± 0.4 | kJ/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase |
By formula: 2H2 + C10H14 = C10H18
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -228. ± 0.4 | kJ/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase |
By formula: 2H2 + C10H14 = C10H18
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -228. ± 0.4 | kJ/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase |
IR Spectrum
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
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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
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 | Chemical Concepts |
NIST MS number | 189558 |
Gas Chromatography
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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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Squalane | 100. | 1130. | Mitra, Mohan, et al., 1974 | H2; Column length: 50. m; Column diameter: 0.2 mm |
Capillary | Squalane | 100. | 1086. | Besson and Gäumann, 1973 | Column length: 50. m; Column diameter: 0.25 mm |
Capillary | Apiezon L | 100. | 1113. | Besson and Gäumann, 1973 | Column length: 50. m; Column diameter: 0.25 mm |
Packed | Methyl Silicone | 130. | 1087. | Antheaume and Guiochon, 1965 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1071.8 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1077.6 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1080.9 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1071.8 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1077.6 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1080.9 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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.
Good and Lee, 1976
Good, W.D.; Lee, S.H.,
The enthalpies of formation of selected naphthalenes, diphenylmethanes, and bicyclic hydrocarbons,
J. Chem. Thermodyn., 1976, 8, 643-650. [all data]
Gollis, Belenyessy, et al., 1962
Gollis, M.H.; Belenyessy, L.I.; Gudzinowicz, B.J.; Koch, S.D.; Smith, J.O.; Wineman, R.J.,
Evaluation of pure hydrocarbons as jet fuels,
J. Chem. Eng. Data, 1962, 7, 331-316. [all data]
Kozina, Skuratov, et al., 1961
Kozina, M.P.; Skuratov, S.M.; Shtekher, S.M.; Sosnina, I.E.; Turova-Polyak, M.B.,
Heats of combustion of some bicyclanes,
Russ. J. Phys. Chem. (Engl. Transl.), 1961, 35, 1144-1146. [all data]
Gollis, Belenyessy, et al., 1962, 2
Gollis, M.H.; Belenyessy, L.I.; Gudzinowicz, B.J.; Koch, S.D.; Smith, J.O.; Wineman, R.J.,
Evaluations of pure hydrocarbons as Jet Fuels,
J. Chem. Eng. Data, 1962, 7, 311-316. [all data]
Kharasch, Hancock, et al., 1956
Kharasch, M.S.; Hancock, J.W.; Nudenberg, W.; Tawney, P.O.,
Factors Influencing the COurse and Mechanism of Grignard Reactions XXII. The Reaction of Grignard Reagents with Alkyl Halides and Ketones in the Presence of Manganous Salts,
J. Org. Chem., 1956, 21, 322. [all data]
McBee, Roberts, et al., 1955
McBee, E.T.; Roberts, C.W.; Idol, J.D.,
J. Am. Chem. Soc., 1955, 77, 4943. [all data]
Boord, Greenlee, et al., 1950
Boord, C.E.; Greenlee, K.W.; Derfer, J.M.,
The Synthesis, Purification and Prop. of Hydrocarbons of Low Mol. Wt., Am. Pet. Inst. Res. Proj. 45, Twelfth Annu. Rep., Ohio State Univ., 1950. [all data]
Boord, Greenlee, et al., 1949
Boord, C.E.; Greenlee, K.W.; Perilstein, W.L.; Derfer, J.M.,
The Synthesis, Purification and Prop. of Hydrocarbons of Low Mol. Wt., Am. Pet. Inst. Res. Proj. 45, Eleventh Annu. Rep., Ohio State Univ., 1949. [all data]
Anonymous, 1948
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 6, Natl. Bur. Stand., 1948. [all data]
Chirico and Steele, 2005
Chirico, R.D.; Steele, W.V.,
Thermodynamic Properties of 2-Methylquinoline and 8-Methylquinoline,
J. Chem. Eng. Data, 2005, 50, 2, 697-708, https://doi.org/10.1021/je049595u
. [all data]
Chirico and Steele, 2004
Chirico, R.D.; Steele, W.V.,
High-energy components of "designer gasoline and designer diesel fuel" I. Heat capacities, enthalpy increments, vapor pressures, critical properties, and derived thermodynamic functions for bicyclopentyl between the T=(10 and 600) K,
The Journal of Chemical Thermodynamics, 2004, 36, 8, 633-643, https://doi.org/10.1016/j.jct.2004.04.003
. [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]
Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R.,
Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld,
Chem. Ber., 1991, 124, 2499-2521. [all data]
Mitra, Mohan, et al., 1974
Mitra, G.D.; Mohan, G.; Sinha, A.,
Gas chromatographic analysis of complex hydrocarbon mixtures,
J. Chromatogr. A, 1974, 91, 633-648, https://doi.org/10.1016/S0021-9673(01)97944-0
. [all data]
Besson and Gäumann, 1973
Besson, R.; Gäumann, T.,
Indices de rétention de cycloalcanes, cycloalcènes, bicycloalkyles, cycloalkyl-cycloalcényles et bicycloalcényles en chromatographie en phase gazeuse,
Helv. Chim. Acta, 1973, 56, 3, 1159-1164, https://doi.org/10.1002/hlca.19730560339
. [all data]
Antheaume and Guiochon, 1965
Antheaume, J.; Guiochon, G.,
Application de la chromatographie en phase gazeuse à l'étude de la composition des fractions moyennes d'un brut pétrolier,
Bull. Soc. Chim. Fr., 1965, 2, 298-307. [all data]
Song, Lai, et al., 2003
Song, C.; Lai, W.-C.; Madhusudan Reddy, K.; Wei, B.,
Chapter 7. Temperature-programmed retention indices for GC and GC-MS of hydrocarbon fuels and simulated distillation GC of heavy oils
in Analytical advances for hydrocarbon research, Hsu,C.S., ed(s)., Kluwer Academic/Plenum Publishers, New York, 2003, 147-193. [all data]
Lai and Song, 1995
Lai, W.-C.; Song, C.,
Temperature-programmed retention indices for g.c. and g.c.-m.s. analysis of coal- and petroleum-derived liquid fuels,
Fuel, 1995, 74, 10, 1436-1451, https://doi.org/10.1016/0016-2361(95)00108-H
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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 ΔfusH Enthalpy of fusion 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
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