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2,4-Hexadiyne

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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
Deltafgas90.20kcal/molCcbLuk'yanova, Pimenova, et al., 1992 

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
Deltafliquid80.1 ± 1.2kcal/molCcbLuk'yanova, Pimenova, et al., 1992ALS
Quantity Value Units Method Reference Comment
Deltacliquid-849.4 ± 1.2kcal/molCcbLuk'yanova, Pimenova, et al., 1992Corresponding «DELTA»fliquid = 80.11 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar42.576cal/mol*KN/ABatley, Mraw, et al., 1982DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
31.924298.15Batley, Mraw, et al., 1982T = 3 to 300 K.; 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:
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
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil402. - 403.KN/AFarchan Laboratories, 1990BS
Tboil402.7KN/AWeast and Grasselli, 1989BS
Tboil403.KN/APrevost, 1926Uncertainty assigned by TRC = 3. K; not clear whether this compound or 1,3-hexadiyne; TRC
Quantity Value Units Method Reference Comment
Tfus337.KN/APauling, Springall, et al., 1939Uncertainty assigned by TRC = 2. K; TRC
Tfus338.KN/APrevost, 1926Uncertainty assigned by TRC = 3. K; not clear whether this compound or 1,3-hexadiyne; TRC
Quantity Value Units Method Reference Comment
Ttriple337.84KN/AMeyer and Meyer, 1986Uncertainty assigned by TRC = 0.15 K; TRC
Quantity Value Units Method Reference Comment
Deltavap10.1kcal/molELuk'yanova, Pimenova, et al., 1992ALS
Deltavap10.2kcal/molEBMeyer and Meyer, 1986, 2Based on data from 364. - 408. K.; AC

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
11. ± 0.5307.MMBatley, Mraw, et al., 1982Based on data from 282. - 333. K.; AC

Enthalpy of phase transition

DeltaHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.2382117.9crystaline, IIcrystaline, IBatley, Mraw, et al., 1982DH

Entropy of phase transition

DeltaStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
2.01117.9crystaline, IIcrystaline, IBatley, Mraw, et al., 1982DH

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:


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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman

View reactions leading to C6H6+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
8.90 ± 0.05PIRosenstock, McCulloh, et al., 1977LLK
8.92PEHeilbronner, Jones, et al., 1977LLK
8.92 ± 0.02PEBieri, Burger, et al., 1977LLK
9.0 ± 0.1EIReeher, Flesch, et al., 1976LLK
8.91PEBrogli, Heilbronner, et al., 1973LLK
9.20EIMomigny, Brakier, et al., 1962RDSH
11.51 ± 0.02SPrice and Walsh, 1945RDSH
9.08PEBieri and Asbrink, 1980Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH3+25.70?EIMomigny, Brakier, et al., 1962RDSH
C3H3+11.99?EIMomigny, Brakier, et al., 1962RDSH
C4H2+14.6 ± 0.1C2H4PIPECODannacher, Stadelmann, et al., 1981LLK
C4H2+14.6 ± 0.1C2H4PIDannacher, 1978LLK
C4H3+14.1 ± 0.1C2H3PIDannacher, 1978LLK
C4H3+15.04?EIMomigny, Brakier, et al., 1962RDSH
C4H4+11.3 ± 0.2C2H2PIRosenstock, McCulloh, et al., 1977LLK
C4H4+12.12C2H2EIMomigny, Brakier, et al., 1962RDSH
C5H3+12.3 ± 0.1CH3PIKompe, Peel, et al., 1993LL
C5H3+13.55CH3EIMomigny, Brakier, et al., 1962RDSH
C6H3+17.99H2+HEIMomigny, Brakier, et al., 1962RDSH
C6H4+11.35H2EIMomigny, Brakier, et al., 1962RDSH
C6H5+9.85HPIOhmichi, Malinovich, et al., 1989LL
C6H5+10.55 ± 0.09HPIRosenstock, McCulloh, et al., 1977LLK
C6H5+11.57HEIMomigny, Brakier, et al., 1962RDSH

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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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

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Download spectrum in JCAMP-DX format.

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)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, NIST Free Links, 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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Mass spectrum
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1.) Enter the desired X axis range (e.g., 100, 200)
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Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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 392

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.


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

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryOV-101891.Zenkevich, 200525. m/0.20 mm/0.10 «mu»m, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C

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

View large format table.

Column type Active phase I Reference Comment
CapillaryMethyl Silicone831.Zenkevich, 1998Program: not specified

References

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

Luk'yanova, Pimenova, et al., 1992
Luk'yanova, V.A.; Pimenova, S.M.; Timofeeva, L.P.; Kozina, M.P.; Kolesov, V.P.; Tarakanova, A.V., Standard enthalpies of formation of some derivatives of diacetylene, Russ. J. Phys. Chem. (Engl. Transl.), 1992, 66, 1083-1085. [all data]

Batley, Mraw, et al., 1982
Batley, M.; Mraw, S.; Staveley, L.A.K.; Overs, A.H.; Owen, M.C.; Thomas, R.K.; White, J.W., The structure and dynamics of crystalline 2,4-hexadiyne. I. Crystal structure, thermodynamics, and model calculations, Mol. Phys., 1982, 45(5), 1015-1034. [all data]

Farchan Laboratories, 1990
Farchan Laboratories, Research Chemicals Catalog, Farchan Laboratories, Gainesville, FL, 1990, 91. [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]

Prevost, 1926
Prevost, C., The Catalytic Dehydrogenation of Vinylalcoylcarbinols, C. R. Hebd. Seances Acad. Sci., 1926, 183, 853. [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]

Meyer and Meyer, 1986
Meyer, E.F.; Meyer, J.J., Vapor Pressure of 2,4-Hexadiyne: Solid(0-21 deg C) and Liquid (91-135 deg C), J. Chem. Eng. Data, 1986, 31, 273. [all data]

Meyer and Meyer, 1986, 2
Meyer, Edwin F.; Meyer, John J., Vapor pressure of 2,4-hexadiyne: solid (0-21.degree.C) and liquid (91-135.degree.C), J. Chem. Eng. Data, 1986, 31, 3, 273-274, https://doi.org/10.1021/je00045a004 . [all data]

Rosenstock, McCulloh, et al., 1977
Rosenstock, H.M.; McCulloh, K.E.; Lossing, F.P., On the mechanisms of C6H6 ionization fragmentation, Int. J. Mass Spectrom. Ion Phys., 1977, 25, 327. [all data]

Heilbronner, Jones, et al., 1977
Heilbronner, E.; Jones, T.B.; Maier, J.P., 170. The ionization energies of di-n-alkyl diacetylenes, Helv. Chim. Acta, 1977, 60, 1697. [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]

Momigny, Brakier, et al., 1962
Momigny, J.; Brakier, L.; D'Or, L., Comparaison entre les effets de l'impact electronique sur le benzene et sur les isomeres du benzene en chaine ouverte, Bull. Classe Sci. Acad. Roy. Belg., 1962, 48, 1002. [all data]

Price and Walsh, 1945
Price, W.C.; Walsh, A.D., The absorption spectra of triple bond molecules in the vacuum ultra violet, J. Chem. Soc. Faraday Trans., 1945, 41, 381. [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]

Dannacher, Stadelmann, et al., 1981
Dannacher, J.; Stadelmann, J.P.; Vogt, J., Competition between dissociative and nondissociative decay of excited perdeutero-2,4-hexadiyne cations, J. Chem. Phys., 1981, 74, 2094. [all data]

Dannacher, 1978
Dannacher, J., Photoelectron-photoion-coincidence measurements on 2,4-hexadiyne, Chem. Phys., 1978, 29, 339. [all data]

Kompe, Peel, et al., 1993
Kompe, B.; Peel, J.B.; Traeger, J.C., A theoretical and experimental study of the structures and stabilities of the [C5H3]+ cation, Org. Mass Spectrom., 1993, 28, 1253. [all data]

Ohmichi, Malinovich, et al., 1989
Ohmichi, N.; Malinovich, Y.; Ziesel, J.P.; Lifshitz, C., Time-dependent mass spectra and breakdown graphs. 12. Competitive dissociative isomerizations of the 2,4-hexadiyne cation, J. Phys. Chem., 1989, 93, 2491. [all data]

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

Zenkevich, 1998
Zenkevich, I.G., Non-Traditional Criteria for Gas-Chromatographic and Chromato-Mass-Spectrometric Identification of Organic Compounds, Zh. Anal. Khim., 1998, 53, 8, 828-835. [all data]


Notes

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