Phenylethyne
- Formula: C8H6
- Molecular weight: 102.1332
- IUPAC Standard InChI: InChI=1S/C8H6/c1-2-8-6-4-3-5-7-8/h1,3-7H
- IUPAC Standard InChIKey: UEXCJVNBTNXOEH-UHFFFAOYSA-N
- CAS Registry Number: 536-74-3
- 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. - Isotopologues:
- Other names: Benzene, ethynyl-; Ethyne, phenyl-; Ethynylbenzene; Phenylacetylene; 1-Phenylethyne; Acetylene, phenyl-; Ethinylbenzene
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase ion energetics data
Go To: Top, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LL - Sharon G. Lias and Joel F. Liebman
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
View reactions leading to C8H6+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 832.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 801.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
| Proton affinity (kJ/mol) | Reference | Comment |
|---|---|---|
| 828.9 | Aue, Guidoni, et al., 2000 | Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM |
Gas basicity at 298K
| Gas basicity (review) (kJ/mol) | Reference | Comment |
|---|---|---|
| 798.7 | Aue, Guidoni, et al., 2000 | Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.82 ± 0.02 | PE | Lichtenberger, Renshaw, et al., 1993 | LL |
| 8.825 ± 0.001 | TE | Dyke, Ozeki, et al., 1992 | LL |
| 8.82 ± 0.08 | PE | Elbel, Lienert, et al., 1981 | LLK |
| 8.9 | EI | Koppel, Schwarz, et al., 1974 | LLK |
| 8.75 | PE | Rabalais and Colton, 1973 | LLK |
| 8.815 ± 0.005 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
| 9.56 ± 0.02 | PE | Deshmukh, Dutta, et al., 1982 | Vertical value; LBLHLM |
| 8.78 | PE | Palmer, Moyes, et al., 1980 | Vertical value; LLK |
| 8.80 | PE | Bock, Aygen, et al., 1980 | Vertical value; LLK |
| 8.82 ± 0.02 | PE | Carlier and Mouvier, 1979 | Vertical value; LLK |
| 8.78 | PE | Griebel, Hohlneicher, et al., 1974 | Vertical value; LLK |
| 8.88 ± 0.02 | PE | Maier and Turner, 1973 | Vertical value; LLK |
De-protonation reactions
C8H5- + =
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1551. ± 9.6 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1518. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, 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.
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Aue, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D.,
Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons,
Int. J. Mass Spectrom., 2000, 201, 283. [all data]
Lichtenberger, Renshaw, et al., 1993
Lichtenberger, D.L.; Renshaw, S.K.; Bullock, R.M.,
Metal-acetylide bonding in (η<5>-C5H5)Fe(CO)2C≡CR compounds. Measures of metal-dπ-acetylide-π interactions from photoelectron spectroscopy,
J. Am. Chem. Soc., 1993, 115, 3276. [all data]
Dyke, Ozeki, et al., 1992
Dyke, J.M.; Ozeki, H.; Takahashi, M.; Cockett, M.C.R.; Kimura, K.,
A study of phenylacetylene and styrene, and their argon complexes PA-Ar and ST-Ar with laser threshold photoelectron spectroscopy,
J. Chem. Phys., 1992, 97, 8926. [all data]
Elbel, Lienert, et al., 1981
Elbel, S.; Lienert, K.; Krebs, A.; tom Dieck, H.,
Phenylethin - mustersonde fur substituenteneffekte,
Liebigs Ann. Chem., 1981, 1785. [all data]
Koppel, Schwarz, et al., 1974
Koppel, C.; Schwarz, H.; Bohlmann, F.,
Elektronenstossinduzierte fragmentierung von acetylenverbindungen,
Org. Mass Spectrom., 1974, 9, 324. [all data]
Rabalais and Colton, 1973
Rabalais, J.W.; Colton, R.J.,
Electronic interaction between the phenyl group and its unsaturated substituents,
J. Electron Spectrosc. Relat. Phenom., 1973, 1, 83. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Deshmukh, Dutta, et al., 1982
Deshmukh, P.; Dutta, T.K.; Hwang, J.L.-S.; Housecroft, C.E.; Fehlner, T.P.,
Photoelectron spectroscopic measurements of the relative charge on carbyne fragments bound to polynuclear cobalt carbonyl clusters,
J. Am. Chem. Soc., 1982, 104, 1740. [all data]
Palmer, Moyes, et al., 1980
Palmer, M.H.; Moyes, W.; Spiers, M.,
The electronic structure of substituted benzenes: Ab initio calculations and photoelectron spectra for benzonitrile, the tolunitriles, fluorobenzonitriles, dicyanobenzenes and ethynylbenzene,
J. Mol. Struct., 1980, 62, 165. [all data]
Bock, Aygen, et al., 1980
Bock, H.; Aygen, S.; Rosmus, P.; Solouki, B.,
Analyse und optimierung von gasphasen-reaktionen. XVII. Selenoketen,
Chem. Ber., 1980, 113, 3187. [all data]
Carlier and Mouvier, 1979
Carlier, P.; Mouvier, G.,
Etude par spectrometrie de photoelectrons de la structure electronique des phenyl-alcynes conjugues,
J. Electron Spectrosc. Relat. Phenom., 1979, 16, 169-181. [all data]
Griebel, Hohlneicher, et al., 1974
Griebel, R.; Hohlneicher, G.; Dorr, F.,
A photoelectron spectroscopic study of benzonitrile, ethynylbenzene and some of its substituted derivatives,
J. Electron Spectrosc. Relat. Phenom., 1974, 4, 185. [all data]
Maier and Turner, 1973
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part 2. Phenylethylenes,
J. Chem. Soc. Faraday Trans. 2, 1973, 69, 196. [all data]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [all data]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.