2,4-Hexadiyne
- Formula: C6H6
- Molecular weight: 78.1118
- IUPAC Standard InChIKey: PCTCNWZFDASPLA-UHFFFAOYSA-N
- CAS Registry Number: 2809-69-0
- 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: Dimethylbutadiyne; Dimethyldiacetylene; CH3C≡CC≡CCH3; Hexa-2,4-diyne
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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 |
---|---|---|---|---|---|
ΔfH°gas | 90.20 | kcal/mol | Ccb | Luk'yanova, Pimenova, et al., 1992 |
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 |
---|---|---|---|---|---|
Tboil | 402. to 403. | K | N/A | Farchan Laboratories, 1990 | BS |
Tboil | 402.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 403. | K | N/A | Prevost, 1926 | Uncertainty assigned by TRC = 3. K; not clear whether this compound or 1,3-hexadiyne; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 337. | K | N/A | Pauling, Springall, et al., 1939 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 338. | K | N/A | Prevost, 1926 | Uncertainty assigned by TRC = 3. K; not clear whether this compound or 1,3-hexadiyne; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 337.84 | K | N/A | Meyer and Meyer, 1986 | Uncertainty assigned by TRC = 0.15 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 10.1 | kcal/mol | E | Luk'yanova, Pimenova, et al., 1992 | ALS |
ΔvapH° | 10.2 | kcal/mol | EB | Meyer and Meyer, 1986, 2 | Based on data from 364. to 408. K.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11. ± 0.5 | 307. | MM | Batley, Mraw, et al., 1982 | Based on data from 282. to 333. K.; AC |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.2382 | 117.9 | crystaline, II | crystaline, I | Batley, Mraw, et al., 1982 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
2.01 | 117.9 | crystaline, II | crystaline, I | Batley, Mraw, et al., 1982 | DH |
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 ± 0.05 | PI | Rosenstock, McCulloh, et al., 1977 | LLK |
8.92 | PE | Heilbronner, Jones, et al., 1977 | LLK |
8.92 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.0 ± 0.1 | EI | Reeher, Flesch, et al., 1976 | LLK |
8.91 | PE | Brogli, Heilbronner, et al., 1973 | LLK |
9.20 | EI | Momigny, Brakier, et al., 1962 | RDSH |
11.51 ± 0.02 | S | Price and Walsh, 1945 | RDSH |
9.08 | PE | Bieri and Asbrink, 1980 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH3+ | 25.70 | ? | EI | Momigny, Brakier, et al., 1962 | RDSH |
C3H3+ | 11.99 | ? | EI | Momigny, Brakier, et al., 1962 | RDSH |
C4H2+ | 14.6 ± 0.1 | C2H4 | PIPECO | Dannacher, Stadelmann, et al., 1981 | LLK |
C4H2+ | 14.6 ± 0.1 | C2H4 | PI | Dannacher, 1978 | LLK |
C4H3+ | 14.1 ± 0.1 | C2H3 | PI | Dannacher, 1978 | LLK |
C4H3+ | 15.04 | ? | EI | Momigny, Brakier, et al., 1962 | RDSH |
C4H4+ | 11.3 ± 0.2 | C2H2 | PI | Rosenstock, McCulloh, et al., 1977 | LLK |
C4H4+ | 12.12 | C2H2 | EI | Momigny, Brakier, et al., 1962 | RDSH |
C5H3+ | 12.3 ± 0.1 | CH3 | PI | Kompe, Peel, et al., 1993 | LL |
C5H3+ | 13.55 | CH3 | EI | Momigny, Brakier, et al., 1962 | RDSH |
C6H3+ | 17.99 | H2+H | EI | Momigny, Brakier, et al., 1962 | RDSH |
C6H4+ | 11.35 | H2 | EI | Momigny, Brakier, et al., 1962 | RDSH |
C6H5+ | 9.85 | H | PI | Ohmichi, Malinovich, et al., 1989 | LL |
C6H5+ | 10.55 ± 0.09 | H | PI | Rosenstock, McCulloh, et al., 1977 | LLK |
C6H5+ | 11.57 | H | EI | Momigny, Brakier, et al., 1962 | RDSH |
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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---|---|
NIST MS number | 392 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 891. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 831. | Zenkevich, 1998 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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.
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]
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]
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]
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, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfH°gas Enthalpy of formation of gas at standard conditions ΔsubH Enthalpy of sublimation ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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