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Phenylethyne

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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 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)832.0kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity801.3kJ/molN/AHunter and Lias, 1998HL

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
828.9Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
798.7Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Ionization energy determinations

IE (eV) Method Reference Comment
8.82 ± 0.02PELichtenberger, Renshaw, et al., 1993LL
8.825 ± 0.001TEDyke, Ozeki, et al., 1992LL
8.82 ± 0.08PEElbel, Lienert, et al., 1981LLK
8.9EIKoppel, Schwarz, et al., 1974LLK
8.75PERabalais and Colton, 1973LLK
8.815 ± 0.005PIWatanabe, Nakayama, et al., 1962RDSH
9.56 ± 0.02PEDeshmukh, Dutta, et al., 1982Vertical value; LBLHLM
8.78PEPalmer, Moyes, et al., 1980Vertical value; LLK
8.80PEBock, Aygen, et al., 1980Vertical value; LLK
8.82 ± 0.02PECarlier and Mouvier, 1979Vertical value; LLK
8.78PEGriebel, Hohlneicher, et al., 1974Vertical value; LLK
8.88 ± 0.02PEMaier and Turner, 1973Vertical value; LLK

De-protonation reactions

C8H5- + Hydrogen cation = Phenylethyne

By formula: C8H5- + H+ = C8H6

Quantity Value Units Method Reference Comment
Deltar1551. ± 9.6kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1518. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas 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 («eta»<5>-C5H5)Fe(CO)2C«equiv»CR compounds. Measures of metal-d«pi»-acetylide-«pi» 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

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