2,4-Hexadiyne
- Formula: C6H6
- Molecular weight: 78.1118
- IUPAC Standard InChI: InChI=1S/C6H6/c1-3-5-6-4-2/h1-2H3
- 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 | 377.4 | kJ/mol | Ccb | Luk'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 |
|---|---|---|---|---|---|
| ΔfH°liquid | 335.2 ± 5.0 | kJ/mol | Ccb | Luk'yanova, Pimenova, et al., 1992 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -3553.7 ± 4.9 | kJ/mol | Ccb | Luk'yanova, Pimenova, et al., 1992 | Corresponding ΔfHºliquid = 335.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 178.14 | J/mol*K | N/A | Batley, Mraw, et al., 1982 | DH |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 133.57 | 298.15 | Batley, Mraw, et al., 1982 | T = 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 |
|---|---|---|---|---|---|
| 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° | 42.2 | kJ/mol | E | Luk'yanova, Pimenova, et al., 1992 | ALS |
| ΔvapH° | 42.5 | kJ/mol | EB | Meyer and Meyer, 1986, 2 | Based on data from 364. to 408. K.; AC |
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 47. ± 2. | 307. | MM | Batley, Mraw, et al., 1982 | Based on data from 282. to 333. K.; AC |
Enthalpy of phase transition
| ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 0.9966 | 117.9 | crystaline, II | crystaline, I | Batley, Mraw, et al., 1982 | DH |
Entropy of phase transition
| ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 8.42 | 117.9 | crystaline, II | crystaline, I | Batley, Mraw, et al., 1982 | DH |
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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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 |
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
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
| 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 |
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
| 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, Condensed phase thermochemistry data, Phase change 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.
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]
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, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid 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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