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1,3-Cyclopentadiene, 5-(1-methylethylidene)-

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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas34.3kcal/molChydRoth, Adamczak, et al., 1991 

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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltacliquid-1115.5 ± 1.2kcal/molCcbDay and Oestreich, 1957Reanalyzed by Cox and Pilcher, 1970, Original value = -1114.5 kcal/mol; Corresponding «DELTA»fliquid = 21.52 kcal/mol (simple calculation by NIST; no Washburn corrections)

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

Quantity Value Units Method Reference Comment
Tfus274.05KN/AMurphy and Duggan, 1949Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Deltavap10.56kcal/molVDay and Oestreich, 1957ALS

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
349.70.066Aldrich Chemical Company Inc., 1990BS
332. - 333.0.033Frinton Laboratories Inc., 1986BS

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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 as indicated in comments:
B - John E. Bartmess
ALS - 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

C8H9- + Hydrogen cation = 1,3-Cyclopentadiene, 5-(1-methylethylidene)-

By formula: C8H9- + H+ = C8H10

Quantity Value Units Method Reference Comment
Deltar354.1 ± 3.2kcal/molG+TSBrickhouse and Squires, 1988gas phase; Acidity between nPrSH, iPrSH; B
Quantity Value Units Method Reference Comment
Deltar347.5 ± 3.0kcal/molIMRBBrickhouse and Squires, 1988gas phase; Acidity between nPrSH, iPrSH; B

3Hydrogen + 1,3-Cyclopentadiene, 5-(1-methylethylidene)- = Cyclopentane, (1-methylethyl)-

By formula: 3H2 + C8H10 = C8H16

Quantity Value Units Method Reference Comment
Deltar-72.2 ± 0.1kcal/molChydRoth, Adamczak, et al., 1991liquid phase; ALS

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 compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C8H10+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
8.03PEHouk, George, et al., 1974Vertical value; LLK

De-protonation reactions

C8H9- + Hydrogen cation = 1,3-Cyclopentadiene, 5-(1-methylethylidene)-

By formula: C8H9- + H+ = C8H10

Quantity Value Units Method Reference Comment
Deltar354.1 ± 3.2kcal/molG+TSBrickhouse and Squires, 1988gas phase; Acidity between nPrSH, iPrSH; B
Quantity Value Units Method Reference Comment
Deltar347.5 ± 3.0kcal/molIMRBBrickhouse and Squires, 1988gas phase; Acidity between nPrSH, iPrSH; B

IR Spectrum

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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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Mass 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.
Origin NIST Mass Spectrometry Data Center, 1994
NIST MS number 135249

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Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-5858.Wu, Zorn, et al., 200530. m/0.32 mm/0.25 «mu»m, He, 40. C @ 2. min, 5. K/min, 250. C @ 5. min

Van Den Dool and Kratz RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryZB-Wax1170.Wu, Zorn, et al., 200530. m/0.32 mm/0.25 «mu»m, He, 40. C @ 2. min, 5. K/min, 250. C @ 5. min

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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.

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]

Day and Oestreich, 1957
Day, J.H.; Oestreich, C., Fulvenes: III. Heat of combustion and resonance energy, J. Org. Chem., 1957, 22, 214-216. [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]

Murphy and Duggan, 1949
Murphy, M.T.; Duggan, A.C., Pyrolysis of Butadiene, J. Am. Chem. Soc., 1949, 71, 3347. [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]

Frinton Laboratories Inc., 1986
Frinton Laboratories Inc., Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [all data]

Brickhouse and Squires, 1988
Brickhouse, M.D.; Squires, R.R., Gas Phase Bronsted vs. Lewis Acid-Base Reactions of 6,6-Dimethylfulvene. A Sensitive Probe of the Electronic Structures of Organic Anions, J. Am. Chem. Soc., 1988, 110, 9, 2706, https://doi.org/10.1021/ja00217a002 . [all data]

Houk, George, et al., 1974
Houk, K.N.; George, J.K.; Duke, R.E., Jr., A frontier molecular orbital treatment of fulvene cycloadditions. Molecular orbital calculations and photoelectron spectra of substituted fulvenes, Tetrahedron, 1974, 30, 523. [all data]

Wu, Zorn, et al., 2005
Wu, S.; Zorn, H.; Krings, U.; Berger, R.G., Characteristic Volatiles from Young and Aged Fruiting Bodies of Wild Polyporus sulfureus (Bull.:Fr.) Fr., J. Agric. Food Chem., 2005, 53, 11, 4524-4528, https://doi.org/10.1021/jf0478511 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References