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
Go To: Top, Gas phase ion energetics data, References, Notes
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 |
Gas phase ion energetics data
Go To: Top, Phase change data, References, Notes
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 |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Notes
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]
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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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