Silane, phenyl-

Formula: C₆H₈Si
Molecular weight: 108.2132
IUPAC Standard InChI: InChI=1S/C6H8Si/c7-6-4-2-1-3-5-6/h1-5H,7H3
IUPAC Standard InChIKey: PARWUHTVGZSQPD-UHFFFAOYSA-N
CAS Registry Number: 694-53-1
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: Benzene, silyl-; Phenylsilane; Phenylsilane, silyl-; Silylbenzene; Fenylsilan
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- Gas Phase Kinetics Database
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Gas phase ion energetics data

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
9.25	PE	Pitt, 1973	LLK
9.09	PE	McLean, 1973	LLK

De-protonation reactions

C₆H₇Si^- + = Silane, phenyl-

By formula: C₆H₇Si^- + H⁺ = C₆H₈Si

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	369.2 ± 2.1	kcal/mol	G+TS	Gal, Decouzon, et al., 2001	gas phase; B
Δ_rH°	368.1 ± 2.1	kcal/mol	G+TS	Wetzel, Salomon, et al., 1989	gas phase; 1.2 kcal/mol stronger than tBuCH(iPr)OH; value altered from reference due to change in acidity scale; B
Δ_rH°	368.7 ± 3.0	kcal/mol	D-EA	Wetzel, Salomon, et al., 1989	gas phase; D-EA cycle give BDE=87.7±2.2 kcal/mol; B
Δ_rH°	370.7 ± 4.1	kcal/mol	G+TS	Damrauer, Kass, et al., 1988	gas phase; Between HF and acetone; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	362.1 ± 2.0	kcal/mol	IMRE	Gal, Decouzon, et al., 2001	gas phase; B
Δ_rG°	361.0 ± 2.0	kcal/mol	IMRE	Wetzel, Salomon, et al., 1989	gas phase; 1.2 kcal/mol stronger than tBuCH(iPr)OH; value altered from reference due to change in acidity scale; B
Δ_rG°	361.5 ± 3.1	kcal/mol	H-TS	Wetzel, Salomon, et al., 1989	gas phase; D-EA cycle give BDE=87.7±2.2 kcal/mol; B
Δ_rG°	363.6 ± 4.0	kcal/mol	IMRB	Damrauer, Kass, et al., 1988	gas phase; Between HF and acetone; B

References

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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]

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]

Notes

Go To: Top, Gas phase ion energetics data, References

Symbols used in this document:

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions