Benzene, 1,1'-(1,4-butanediyl)bis-

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

Quantity Value Units Method Reference Comment
Δcsolid-8858.7 ± 2.0kJ/molCcbCoops, Hoijtink, et al., 1953Reanalyzed by Cox and Pilcher, 1970, Original value = -8858. ± 2. kJ/mol; Corresponding Δfsolid = -9.93 kJ/mol (simple calculation by NIST; no Washburn corrections)
Δcsolid-8912.kJ/molCcbSerijan and Wise, 1952Corresponding Δfsolid = 42. kJ/mol (simple calculation by NIST; no Washburn corrections)
Δcsolid-9121.1kJ/molCcbWise, Serijan, et al., 1951Corresponding Δfsolid = 252. kJ/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

Quantity Value Units Method Reference Comment
Tboil590.2KN/AWeast and Grasselli, 1989BS
Tboil589.06KN/ASerijan and Wise, 1952, 2Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tfus326. ± 3.KAVGN/AAverage of 9 values; Individual data points

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 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

2Hydrogen + 1,3-Butadiene, 1,4-diphenyl-, (E,E)- = Benzene, 1,1'-(1,4-butanediyl)bis-

By formula: 2H2 + C16H14 = C16H18

Quantity Value Units Method Reference Comment
Δr-184.26 ± 0.62kJ/molChydWilliams, 1942liquid phase; solvent: Acetic acid; At 302 K

4Hydrogen + Benzene, 1,1'-(1,3-butadiyne-1,4-diyl)bis- = Benzene, 1,1'-(1,4-butanediyl)bis-

By formula: 4H2 + C16H10 = C16H18

Quantity Value Units Method Reference Comment
Δr-495.8 ± 4.1kJ/molChydDavis, Allinger, et al., 1985liquid phase; solvent: Hexane

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 evaluated by: Edward P. Hunter and Sharon G. Lias

Quantity Value Units Method Reference Comment
Proton affinity (review)822.0kJ/molN/AHunter and Lias, 1998 
Quantity Value Units Method Reference Comment
Gas basicity779.8kJ/molN/AHunter and Lias, 1998 

IR Spectrum

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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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 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
State gas
Instrument HP-GC/MS/IRD

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


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 Japan AIST/NIMC Database- Spectrum MS-IW-4247
NIST MS number 244331

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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

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Column type Active phase Temperature (C) I Reference Comment
PackedApiezon L170.1780.Kríz, Popl, et al., 1974 
PackedApiezon L185.1793.Kríz, Popl, et al., 1974 

Kovats' RI, polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillarySP-1000185.2398.Kríz, Popl, et al., 1974N2; Column length: 50. m; Column diameter: 0.25 mm
CapillarySP-1000200.2355.Kríz, Popl, et al., 1974N2; Column length: 50. m; Column diameter: 0.25 mm

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

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Column type Active phase I Reference Comment
CapillarySE-541742.9Shapi and Hesso, 199025. m/0.32 mm/0.15 μm, He, 40. C @ 1. min, 5. K/min, 280. C @ 15. min

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryDB-11756.Hathcock and Bertsch, 1993100. m/0.25 mm/0.5 μm; Program: not specified

References

Go To: Top, 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.

Coops, Hoijtink, et al., 1953
Coops, J.; Hoijtink, G.J.; Kramer, TH.J.E., Thermochemical investigations on arylethanes. II. Heats of combustion of some para and ortho tolylthanes and phenylbutanes., Rec. Trav. Chim. Pays/Bas, 1953, 72, 793. [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]

Serijan and Wise, 1952
Serijan, K.T.; Wise, P.H., Dicyclic hydrocarbons. V. Synthesis and physical properties of the diphenyl- and dicyclohexylbutanes, J. Am. Chem. Soc., 1952, 74, 365-368. [all data]

Wise, Serijan, et al., 1951
Wise, C.H.; Serijan, K.T.; Goodman, I.A., NACA Technical Report 1003, NACA Technical Report 1003, 1951, 1-10. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Serijan and Wise, 1952, 2
Serijan, K.T.; Wise, P.H., Dicyclic hydrocarbons. V. Synthesis and physical properties of the diphenyl - and dicyclohexylbutanes, J. Am. Chem. Soc., 1952, 74, 365-8. [all data]

Williams, 1942
Williams, R.B., Heats of catalytic hydrogenation in solution. I. Apparatus, technique, and the heats of hydrogenation of certain pairs of stereoisomers, J. Am. Chem. Soc., 1942, 64, 1395-1404. [all data]

Davis, Allinger, et al., 1985
Davis, H.E.; Allinger, N.L.; Rogers, D.W., Enthalpies of hydrogenation of phenylalkynes: indirect determination of the enthalpy of formation of diphenylcyclopropenone, J. Org. Chem., 1985, 50, 3601-3604. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Kríz, Popl, et al., 1974
Kríz, J.; Popl, M.; Mostecký, J., Retention indices of biphenyls and diphenylalkanes, J. Chromatogr., 1974, 97, 1, 3-13, https://doi.org/10.1016/S0021-9673(01)97577-6 . [all data]

Shapi and Hesso, 1990
Shapi, M.M.; Hesso, A., Thermal decomposition of polystyrene volatile compounds from large-scale pyrolysis, J. Anal. Appl. Pyrolysis, 1990, 18, 2, 143-161, https://doi.org/10.1016/0165-2370(90)80004-8 . [all data]

Hathcock and Bertsch, 1993
Hathcock, S.; Bertsch, W., Analysis of volatiles associated with industrial scale processing of expanded polystyrene. Part II: Identification and quantitation, J. Hi. Res. Chromatogr., 1993, 16, 11, 651-659, https://doi.org/10.1002/jhrc.1240161106 . [all data]


Notes

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