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1,3-Butadiyne

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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 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
Deltafgas464.kJ/molKinKiefer, Sidhu, et al., 1992ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
30.3050.Dorofeeva O.V., 1991Recommended values are in good agreement with other statistically calculated values [52FER/WER]. There is an appreciable difference with values calculated by [ Dessau L., 1988] because these authors used the estimated values of vibrational frequencies instead of experimental ones.; GT
37.87100.
47.35150.
57.50200.
70.17273.15
73.7 ± 1.0298.15
73.92300.
84.43400.
91.51500.
96.86600.
101.26700.
105.05800.
108.38900.
111.331000.
113.931100.
116.241200.
118.271300.
120.061400.
121.641500.
123.041600.
124.271700.
125.371800.
126.341900.
127.202000.

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
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil284. ± 3.KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus263.KN/APauling, Springall, et al., 1939Uncertainty assigned by TRC = 2. K; TRC
Tfus237.7KN/AStraus and Kollek, 1926Uncertainty assigned by TRC = 2.5 K; TRC
Tfus237.KN/AMueller, 1925Uncertainty assigned by TRC = 3. K; TRC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
25.4258.N/AStraus and Kollek, 2006Based on data from 195. - 273. K. See also Boublik, Fried, et al., 1984.; AC
33.4219.N/ATanneberger, 2006Based on data from 188. - 234. K. See also Boublik, Fried, et al., 1984.; AC
26.1268.AStephenson and Malanowski, 1987Based on data from 237. - 283. K. See also Dykyj, 1971.; AC
26.4267.N/AStull, 1947Based on data from 191. - 282. K.; AC

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
190.7 - 282.93.05288570.271-95.334Stull, 1947Coefficents calculated by NIST from author's data.
195.0 - 273.2.64407460.684-108.556Straus and Kollek, 1926, 2Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
36.3188. - 234.N/ATanneberger, 2006AC
36.2211.AStull, 1947Based on data from 190. - 232. K.; AC

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: John E. Bartmess

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

C4H- + Hydrogen cation = 1,3-Butadiyne

By formula: C4H- + H+ = C4H2

Quantity Value Units Method Reference Comment
Deltar1507. ± 13.kJ/molD-EAPino, Tulej, et al., 2002gas phase
Deltar1508. ± 12.kJ/molEndoShi and Ervin, 2000gas phase
Quantity Value Units Method Reference Comment
Deltar1473. ± 14.kJ/molH-TSPino, Tulej, et al., 2002gas phase
Deltar1474. ± 13.kJ/molH-TSShi and Ervin, 2000gas phase

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/kg*bar)
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/kg*bar) d(ln(kH))/d(1/T) (K) Method Reference Comment
0.19 QN/A missing citation give several references for the Henry's law constants but don't assign them to specific species.

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 as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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 C4H2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)737.2kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity712.8kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
10.17PEBieri, Schmelzer, et al., 1980LLK
10.17 ± 0.02PEBieri, Burger, et al., 1977LLK
10.1 ± 0.1EIReeher, Flesch, et al., 1976LLK
10.17PEBrogli, Heilbronner, et al., 1973LLK
10.180 ± 0.003SSmith, 1967RDSH
10.17 ± 0.01PEBaker and Turner, Commun. 1967RDSH
10.30PEBieri and Asbrink, 1980Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H+20.1 ± 0.5C2HEICoats and Anderson, 1957RDSH
C4H+12.1 ± 0.3HEICoats and Anderson, 1957RDSH

De-protonation reactions

C4H- + Hydrogen cation = 1,3-Butadiyne

By formula: C4H- + H+ = C4H2

Quantity Value Units Method Reference Comment
Deltar1507. ± 13.kJ/molD-EAPino, Tulej, et al., 2002gas phase; B
Deltar1508. ± 12.kJ/molEndoShi and Ervin, 2000gas phase; B
Quantity Value Units Method Reference Comment
Deltar1473. ± 14.kJ/molH-TSPino, Tulej, et al., 2002gas phase; B
Deltar1474. ± 13.kJ/molH-TSShi and Ervin, 2000gas phase; B

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.
NIST MS number 87

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Fihtengolts, et al., 1969
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 20172
Instrument SF-4
Melting point 10

Vibrational and/or electronic energy levels

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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: Takehiko Shimanouchi

Symmetry:   Dinftyh     Symmetry Number sigma = 2


 Sym.   No   Approximate   Selected Freq.  Infrared   Raman   Comments 
 Species   type of mode   Value   Rating   Value  Phase  Value  Phase

«sigma»g+ 1 CH str 3293  D  ia 3293 VW liq.
«sigma»g+ 2 C«equiv»C str 2184  C  ia 2184 VS gas
«sigma»g+ 3 C-C str 874  C  ia 874 W gas
«sigma»u+ 4 CH str 3329  C 3329 VS gas  ia
«sigma»u+ 5 C«equiv»C str 2020  C 2020 M gas  ia
«pi»g 6 CH bend 627  C  ia 627 M gas
«pi»g 7 CCC bend 482  C  ia 482 S gas
«pi»u 8 CH bend 630  B 630 VS gas  ia
«pi»u 9 CCC bend 231  E  ia 231 VW liq.

Source: Shimanouchi, 1972

Notes

VSVery strong
SStrong
MMedium
WWeak
VWVery weak
iaInactive
B1~3 cm-1 uncertainty
C3~6 cm-1 uncertainty
D6~15 cm-1 uncertainty
E15~30 cm-1 uncertainty

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
CapillaryCP Sil 5 CB20.431.Do and Raulin, 199225. m/0.15 mm/2. «mu»m, H2

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

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-1445.Kaiser and Siegl, 199460. m/0.32 mm/1. «mu»m, -50. C @ 4. min, 6. K/min; Tend: 180. C

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxane: CP-Sil 5 CB428.Bramston-Cook, 201360. m/0.25 mm/1.0 «mu»m, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min
CapillaryOV-101430.Zenkevich, 200525. m/0.20 mm/0.10 «mu»m, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Vibrational and/or electronic energy levels, Gas Chromatography, NIST Free Links, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Kiefer, Sidhu, et al., 1992
Kiefer, J.H.; Sidhu, S.S.; Kern, R.D.; Xie, K.; Chen, H.; Harding, L.B., The homogeneous pyrolysis of acetylene II: the high temperature radical chain mechanism, Combust. Sci. Technol., 1992, 82, 101-130. [all data]

Dorofeeva O.V., 1991
Dorofeeva O.V., Thermodynamic properties of linear carbon chain molecules with conjugated triple bonds. Part I. Polyacetylenes, H(CC)nH (n=2-6), cyanopolyacetylenes, H(CC)nCN (n=1-5), and dicyanopolyacetylenes, NC(CC)nCN (n=1-4), Thermochim. Acta, 1991, 178, 273-286. [all data]

Dessau L., 1988
Dessau L., Vibrations and thermodynamic functions of long-chain acetylenes, Z. Phys. Chem. (Leipzig), 1988, 269, 187-190. [all data]

Pauling, Springall, et al., 1939
Pauling, L.; Springall, H.D.; Palmer, K.J., The Electron Diffraction Investigation of Methylacetylene, Dimethyl- acetylene, Dimethyldiacetylene, Methyl Cyanide, Diacetylene and Cyanogen cyanogen, J. Am. Chem. Soc., 1939, 61, 927-8. [all data]

Straus and Kollek, 1926
Straus, F.; Kollek, L., About Diacetylene, Ber. Dtsch. Chem. Ges., 1926, 59, 1664-81. [all data]

Mueller, 1925
Mueller, F.G., Diacetylene (1,3-butadiyne), Helv. Chim. Acta, 1925, 8, 826-32. [all data]

Straus and Kollek, 2006
Straus, Fritz; Kollek, Leo, Über Diacetylen, Ber. dtsch. Chem. Ges. A/B, 2006, 59, 8, 1664-1681, https://doi.org/10.1002/cber.19260590804 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Tanneberger, 2006
Tanneberger, H., Einige Bemerkungen über die Dampfdruck-Kurve des Diacetylens (Butadiins)., Ber. dtsch. Chem. Ges. A/B, 2006, 66, 4, 484-486, https://doi.org/10.1002/cber.19330660408 . [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]

Dykyj, 1971
Dykyj, J., Petrochemia, 1971, 11, 2, 27. [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Straus and Kollek, 1926, 2
Straus, F.; Kollek, L., Uber Diacetylen, Ber. Dtsch. Chem. Ges., 1926, 59, 8, 1664-1681, https://doi.org/10.1002/cber.19260590804 . [all data]

Pino, Tulej, et al., 2002
Pino, T.; Tulej, M.; Guthe, F.; Pachkov, M.; Maier, J.P., Photodetachment spectroscopy of the C2nH- (n=2-4) anions in the vicinity of their electron detachment threshold, J. Chem. Phys., 2002, 116, 14, 6126-6131, https://doi.org/10.1063/1.1451248 . [all data]

Shi and Ervin, 2000
Shi, Y.; Ervin, K.M., Gas-phase acidity and C-H bond energy of diacetylene, Chem. Phys. Lett., 2000, 318, 1-3, 149-154, https://doi.org/10.1016/S0009-2614(00)00023-3 . [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]

Bieri, Schmelzer, et al., 1980
Bieri, G.; Schmelzer, A.; Asbrink, L.; Jonsson, M., Fluorine and the fluoroderivatives of acetylene and diacetylene studied by 30.4 nm He(II) photoelectron spectroscopy, Chem. Phys., 1980, 49, 213. [all data]

Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P., Valence ionization enrgies of hydrocarbons, Helv. Chim. Acta, 1977, 60, 2213. [all data]

Reeher, Flesch, et al., 1976
Reeher, J.R.; Flesch, G.D.; Svec, H.J., The mass spectra and ionization potentials of the neutral fragments produced during the electron bombardment of aromatic compounds, Org. Mass Spectrom., 1976, 11, 154. [all data]

Brogli, Heilbronner, et al., 1973
Brogli, F.; Heilbronner, E.; Hornung, V.; Kloster-Jensen, E., 230. Die photoelektronen-spektren methyl-substituierter Acetylene, Helv. Chim. Acta, 1973, 56, 2171. [all data]

Smith, 1967
Smith, W.L., The absorption spectrum of diacetylene in the vacuum ultraviolet, Proc. Roy. Soc. (London), 1967, A300, 519. [all data]

Baker and Turner, Commun. 1967
Baker, C.; Turner, D.W., Photoelectron spectra of acetylene, diacetylene, and their deutero-derivatives, Chem., Commun. 1967, 797. [all data]

Bieri and Asbrink, 1980
Bieri, G.; Asbrink, L., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1980, 20, 149. [all data]

Coats and Anderson, 1957
Coats, F.H.; Anderson, R.C., Thermodynamic data from electron-impact measurements on acetylene and substituted acetylenes, J. Am. Chem. Soc., 1957, 79, 1340. [all data]

Fihtengolts, et al., 1969
Fihtengolts, V.S., et al., Atlas of UV Absorption Spectra of Substances Used in Synthetic Rubber Manufacture, 1969, 172. [all data]

Shimanouchi, 1972
Shimanouchi, T., Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [all data]

Do and Raulin, 1992
Do, L.; Raulin, F., Gas chromatography of Titan's atmosphere. III. Analysis of low-molecular-weight hydrocarbons and nitriles with a CP-Sil-5 CB WCOT capillary column, J. Chromatogr., 1992, 591, 1-2, 297-301, https://doi.org/10.1016/0021-9673(92)80247-R . [all data]

Kaiser and Siegl, 1994
Kaiser, E.W.; Siegl, W.O., High resolution gas chromatographic determination of the atmospheric reactivity of engine-out hydrocarbon emissions from a spark-ignited engine, J. Hi. Res. Chromatogr., 1994, 17, 4, 264-270, https://doi.org/10.1002/jhrc.1240170414 . [all data]

Bramston-Cook, 2013
Bramston-Cook, R., Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Vibrational and/or electronic energy levels, Gas Chromatography, NIST Free Links, References