Silane, phenyl-


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: John E. Bartmess

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Individual Reactions

C6H7Si- + Hydrogen cation = Silane, phenyl-

By formula: C6H7Si- + H+ = C6H8Si

Quantity Value Units Method Reference Comment
Δr369.2 ± 2.1kcal/molG+TSGal, Decouzon, et al., 2001gas phase
Δr368.1 ± 2.1kcal/molG+TSWetzel, Salomon, et al., 1989gas phase; 1.2 kcal/mol stronger than tBuCH(iPr)OH; value altered from reference due to change in acidity scale
Δr368.7 ± 3.0kcal/molD-EAWetzel, Salomon, et al., 1989gas phase; D-EA cycle give BDE=87.7±2.2 kcal/mol
Δr370.7 ± 4.1kcal/molG+TSDamrauer, Kass, et al., 1988gas phase; Between HF and acetone
Quantity Value Units Method Reference Comment
Δr362.1 ± 2.0kcal/molIMREGal, Decouzon, et al., 2001gas phase
Δr361.0 ± 2.0kcal/molIMREWetzel, Salomon, et al., 1989gas phase; 1.2 kcal/mol stronger than tBuCH(iPr)OH; value altered from reference due to change in acidity scale
Δr361.5 ± 3.1kcal/molH-TSWetzel, Salomon, et al., 1989gas phase; D-EA cycle give BDE=87.7±2.2 kcal/mol
Δr363.6 ± 4.0kcal/molIMRBDamrauer, Kass, et al., 1988gas phase; Between HF and acetone

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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV) Method Reference Comment
9.25PEPitt, 1973LLK
9.09PEMcLean, 1973LLK

De-protonation reactions

C6H7Si- + Hydrogen cation = Silane, phenyl-

By formula: C6H7Si- + H+ = C6H8Si

Quantity Value Units Method Reference Comment
Δr369.2 ± 2.1kcal/molG+TSGal, Decouzon, et al., 2001gas phase; B
Δr368.1 ± 2.1kcal/molG+TSWetzel, Salomon, et al., 1989gas phase; 1.2 kcal/mol stronger than tBuCH(iPr)OH; value altered from reference due to change in acidity scale; B
Δr368.7 ± 3.0kcal/molD-EAWetzel, Salomon, et al., 1989gas phase; D-EA cycle give BDE=87.7±2.2 kcal/mol; B
Δr370.7 ± 4.1kcal/molG+TSDamrauer, Kass, et al., 1988gas phase; Between HF and acetone; B
Quantity Value Units Method Reference Comment
Δr362.1 ± 2.0kcal/molIMREGal, Decouzon, et al., 2001gas phase; B
Δr361.0 ± 2.0kcal/molIMREWetzel, Salomon, et al., 1989gas phase; 1.2 kcal/mol stronger than tBuCH(iPr)OH; value altered from reference due to change in acidity scale; B
Δr361.5 ± 3.1kcal/molH-TSWetzel, Salomon, et al., 1989gas phase; D-EA cycle give BDE=87.7±2.2 kcal/mol; B
Δr363.6 ± 4.0kcal/molIMRBDamrauer, Kass, et al., 1988gas phase; Between HF and acetone; B

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.

Gal, Decouzon, et al., 2001
Gal, J.F.; Decouzon, M.; Maria, P.C.; Gonzalez, A.I.; Mo, O.; Yanez, M.; El Chaouch, S.; Guillemin, J.C., Acidity trends in alpha,beta-unsaturated alkanes, silanes, germanes, and stannanes, J. Am. Chem. Soc., 2001, 123, 26, 6353-6359, https://doi.org/10.1021/ja004079j . [all data]

Wetzel, Salomon, et al., 1989
Wetzel, D.M.; Salomon, K.E.; Berger, S.; Brauman, J.I., Gas-Phase Acidities of Organosilanes and Electron Affinities of Organosilyl Radicals, J. Am. Chem. Soc., 1989, 111, 11, 3835, https://doi.org/10.1021/ja00193a013 . [all data]

Damrauer, Kass, et al., 1988
Damrauer, R.; Kass, S.R.; DePuy, C.H., Gas-Phase Acidities of Methylsilanes: C-H versus Si-H, Organomet., 1988, 7, 3, 637, https://doi.org/10.1021/om00093a011 . [all data]

Pitt, 1973
Pitt, C.G., Hyperconjugation and its role in group IV chemistry, J. Organomet. Chem., 1973, 61, 49. [all data]

McLean, 1973
McLean, R.A.N., The bonding of a silicon atom with a phenyl ring: The photoelectron spectrum of phenylsilane, Can. J. Chem., 1973, 51, 2089. [all data]


Notes

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