1,5-Hexadiyne
- Formula: C6H6
- Molecular weight: 78.1118
- IUPAC Standard InChIKey: YFIBSNDOVCWPBL-UHFFFAOYSA-N
- CAS Registry Number: 628-16-0
- 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: Bipropargyl; Dipropargyl; HCCCH2CH2CCH; hexa-1,5-diyne
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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 |
---|---|---|---|---|---|
Tboil | 359. | K | N/A | Farchan Laboratories, 1990 | BS |
Tboil | 359.15 | K | N/A | Skinner and Snelson, 1959 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tboil | 361. | K | N/A | Pomerantz, Fookson, et al., 1954 | Uncertainty assigned by TRC = 0.15 K; TRC |
Tboil | 358.6 | K | N/A | Perkin, 1895 | Uncertainty assigned by TRC = 3. K; TRC |
Tboil | 360. | K | N/A | Griner, 1892 | Uncertainty assigned by TRC = 6. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 267. | K | N/A | Griner, 1892 | Uncertainty assigned by TRC = 4. K; TRC |
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
By formula: 4H2 + C6H6 = C6H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -582.8 ± 4.2 | kJ/mol | Chyd | Skinner and Snelson, 1959, 2 | liquid phase; solvent: Acetic acid; Reanalyzed by Cox and Pilcher, 1970, Original value = -583.2 ± 4.2 kJ/mol |
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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 |
---|---|---|---|
9.93 ± 0.05 | EI | Rosenstock, McCulloh, et al., 1977 | LLK |
9.98 ± 0.05 | PI | Rosenstock, McCulloh, et al., 1977 | LLK |
9.90 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.87 ± 0.03 | EI | Gross and Aerni, 1973 | LLK |
10.35 | EI | Momigny, Brakier, et al., 1962 | RDSH |
10.0 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
10.48 | PE | Bischof, Gleiter, et al., 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H3+ | 12.17 | ? | EI | Momigny, Brakier, et al., 1962 | RDSH |
C4H2+ | 15.02 | ? | EI | Momigny, Brakier, et al., 1962 | RDSH |
C4H3+ | 15.45 | ? | EI | Momigny, Brakier, et al., 1962 | RDSH |
C4H4+ | 10.42 ± 0.08 | C2H2 | PI | Rosenstock, McCulloh, et al., 1977 | LLK |
C4H4+ | 10.5 ± 0.1 | C2H2 | EI | Rosenstock, McCulloh, et al., 1977 | LLK |
C4H4+ | 11.4 | C2H2 | EI | Momigny, Brakier, et al., 1962 | RDSH |
C5H3+ | 11.9 ± 0.2 | ? | PI | Kompe, Peel, et al., 1993 | LL |
C6H4+ | 11.17 | H2 | EI | Momigny, Brakier, et al., 1962 | RDSH |
C6H5+ | 10.16 ± 0.08 | H | PI | Rosenstock, McCulloh, et al., 1977 | LLK |
C6H5+ | 10.21 ± 0.03 | H | EI | Gross and Aerni, 1973 | LLK |
C6H5+ | 11.47 | H | EI | Momigny, Brakier, et al., 1962 | RDSH |
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. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-4647 |
NIST MS number | 231272 |
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, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 680. | Zenkevich, 1998 | Program: not specified |
References
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Farchan Laboratories, 1990
Farchan Laboratories,
Research Chemicals Catalog, Farchan Laboratories, Gainesville, FL, 1990, 91. [all data]
Skinner and Snelson, 1959
Skinner, H.A.; Snelson, A.,
Heats of Hydrogenation. Part 3,
Trans. Faraday Soc., 1959, 55, 404. [all data]
Pomerantz, Fookson, et al., 1954
Pomerantz, P.; Fookson, A.; Mears, T.W.; Rothberg, S.; Howard, F.L.,
Synthesis and Physical Properties of Several Acetylenic Hydrocarbons,
J. Res. Natl. Bur. Stand. (U. S.), 1954, 52, 51. [all data]
Perkin, 1895
Perkin, W.H.,
J. Chem. Soc., 1895, 67, 255-64. [all data]
Griner, 1892
Griner, G.,
Ann. Chim., 1892, 26, 347. [all data]
Skinner and Snelson, 1959, 2
Skinner, H.A.; Snelson, A.,
Heats of hydrogenation Part 3.,
Trans. Faraday Soc., 1959, 55, 405-407. [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]
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]
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]
Gross and Aerni, 1973
Gross, M.L.; Aerni, R.J.,
The unusual loss of hydrogen from ionized 1,5-hexadiyne,
J. Am. Chem. Soc., 1973, 95, 7875. [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]
Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W.,
30.4-nm He(II) photoelectron spectra of organic molecules,
J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]
Bischof, Gleiter, et al., 1975
Bischof, P.; Gleiter, R.; Hopf, H.; Lenich, F.T.,
Photoelectron spectra of open chain C6H6 isomers,
J. Am. Chem. Soc., 1975, 97, 5467. [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]
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
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- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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