Thioacetone

Formula: C₃H₆S
Molecular weight: 74.145
IUPAC Standard InChI: InChI=1S/C3H6S/c1-3(2)4/h1-2H3
IUPAC Standard InChIKey: JTNXQVCPQMQLHK-UHFFFAOYSA-N
CAS Registry Number: 4756-05-2
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Species with the same structure:
- 2-thioxo-propane
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Reaction thermochemistry data

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Data compiled by: John E. Bartmess

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Individual Reactions

C₃H₅S^- + = Thioacetone

By formula: C₃H₅S^- + H⁺ = C₃H₆S

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1469. ± 14.	kJ/mol	G+TS	Zhang and Grabowski, 1989	gas phase; Between H2S, PhOH (Acid = Me2C=S)
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1439. ± 13.	kJ/mol	IMRB	Zhang and Grabowski, 1989	gas phase; Between H2S, PhOH (Acid = Me2C=S)

Gas phase ion energetics data

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Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₃H₆S⁺ (ion structure unspecified)

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.6	PE	Rao, 1975	Vertical value; LLK
8.60 ± 0.05	PE	Kroto, Landsberg, et al., 1974	Vertical value; LLK

De-protonation reactions

C₃H₅S^- + = Thioacetone

By formula: C₃H₅S^- + H⁺ = C₃H₆S

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1469. ± 14.	kJ/mol	G+TS	Zhang and Grabowski, 1989	gas phase; Between H2S, PhOH (Acid = Me2C=S); B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1439. ± 13.	kJ/mol	IMRB	Zhang and Grabowski, 1989	gas phase; Between H2S, PhOH (Acid = Me2C=S); B

Vibrational and/or electronic energy levels

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Data compiled by: Marilyn E. Jacox

State: E

Energy (cm^-1)	Med.	Transition	λ_min (nm)	λ_max (nm)	References


T_o = 52329	gas	E-X	189	191	Judge, Moule, et al., 1983

Vib. sym.	No.	Approximate type of mode	cm^-1	Med.	Method	References


a₁	8	C₃ deform.	259 ± 5	gas	AB	Paone, Moule, et al., 1984

State: D

Energy (cm^-1)	Med.	Transition	λ_min (nm)	λ_max (nm)	References


T_o = 51520	gas	D-X	192	194	Judge, Moule, et al., 1983

Vib. sym.	No.	Approximate type of mode	cm^-1	Med.	Method	References


a₁	8	C₃ deform.	310 ± 7	gas	AB	Paone, Moule, et al., 1984

State: C

Energy (cm^-1)	Med.	Transition	λ_min (nm)	λ_max (nm)	References


T_o = 44256	gas	C-X	212	228	Judge, Moule, et al., 1983

Vib. sym.	No.	Approximate type of mode	cm^-1	Med.	Method	References


a₁	1	CH₃ stretch	2785	gas	AB	Paone, Moule, et al., 1984
	3	C=S stretch	1308	gas	AB	Paone, Moule, et al., 1984
	5	CH₃ deform.	1192	gas	AB	Paone, Moule, et al., 1984
	6	C₃ deform.	323	gas	AB	Judge, Moule, et al., 1983 Paone, Moule, et al., 1984
		Torsion	117	gas	AB	Paone, Moule, et al., 1984

State: B

Energy (cm^-1)	Med.	Transition	λ_min (nm)	λ_max (nm)	References


T_x = 45500 ± 100	gas	B-X	200	250	Judge, Moule, et al., 1983

State: A

Energy (cm^-1)	Med.	Transition	λ_min (nm)	λ_max (nm)	References


T_o = 18800 ± 100	gas	A-X	410	510	Judge, Moule, et al., 1983

Vib. sym.	No.	Approximate type of mode	cm^-1		Med.	Method	References


a₁	3	CS stretch	633		gas	AB	Paone, Moule, et al., 1984
a₂	9	CH₃ stretch	2960	T	gas	AB	Paone, Moule, et al., 1984

State: a

Energy (cm^-1)	Med.	Transition	λ_min (nm)	λ_max (nm)	References


T_o = 17327.8	gas	a-X	510	587	Judge, Moule, et al., 1983

Vib. sym.	No.	Approximate type of mode	cm^-1	Med.	Method	References


a'	10	CS stretch	642.5	gas	AB LF	Judge, Moule, et al., 1983 Paone, Moule, et al., 1984 Moule, Smeyers, et al., 1991
	11	C₃ deform.	318.3	gas	LF	Moule, Smeyers, et al., 1991
	12	S wag	195.0	gas	LF	Moule, Smeyers, et al., 1991
	13	CH₃ torsion	127.0	gas	LF	Moule, Smeyers, et al., 1991

State: X

Vib. sym.	No.	Approximate type of mode	cm^-1	Med.	Method	References


a₁	8	C₃ deform.	363	gas	AB	Judge, Moule, et al., 1983 Paone, Moule, et al., 1984
b₁	17	S wag	153.2	gas	LF	Moule, Smeyers, et al., 1991

Additional references: Jacox, 1994, page 415; Kroto, Landsberg, et al., 1974; Bruno, Moule, et al., 1989

Notes

Tentative assignment or approximate value

Energy separation between the v = 0 levels of the excited and electronic ground states.

Energy separation between the band maximum of the excited electronic state and the v = 0 level of the ground state.

References

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Zhang and Grabowski, 1989
Zhang, L.; Grabowski, J.J., The Gas-Phase Basicity and H/D Exchange Characteristics of the Parent Thiocarbonyl Enolate Anions, J. Chem. Soc. Chem. Comm. 1819, 1989. [all data]

Rao, 1975
Rao, C.N.R., Lone-pair ionization bands of chromophores in the photoelectron spectra of organic molecules, Indian J. Chem., 1975, 13, 950. [all data]

Kroto, Landsberg, et al., 1974
Kroto, H.W.; Landsberg, B.M.; Suffolk, R.J.; Vodden, A., The photoelectron and microwave spectra of the unstable species thioacetaldehyde, CH₃CHS, and thioacetone, (CH₃)₂CS, Chem. Phys. Lett., 1974, 29, 265. [all data]

Judge, Moule, et al., 1983
Judge, R.H.; Moule, D.C.; Bruno, A.E.; Steer, R.P., Thioketone spectroscopy: An analysis of the lower electronic transitions in thioacetone and thioacetaldehyde, Chem. Phys. Lett., 1983, 102, 4, 385, https://doi.org/10.1016/0009-2614(83)87061-4 . [all data]

Paone, Moule, et al., 1984
Paone, S.; Moule, D.C.; Bruno, A.E.; Steer, R.P., Vibronic analyses of the Rydberg and lower intravalence electronic transitions in thioacetone, J. Mol. Spectrosc., 1984, 107, 1, 1, https://doi.org/10.1016/0022-2852(84)90260-1 . [all data]

Moule, Smeyers, et al., 1991
Moule, D.C.; Smeyers, Y.G.; Senent, M.L.; Clouthier, D.J.; Karolczak, J.; Judge, R.H., An analysis of the methyl rotation dynamics in the S0 (X 1A1) and T1 (a 3A2) states of thioacetone, (CH3)2CS and (CD3)2CS from pyrolysis jet spectra, J. Chem. Phys., 1991, 95, 5, 3137, https://doi.org/10.1063/1.460871 . [all data]

Jacox, 1994
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules, American Chemical Society, Washington, DC, 1994, 464. [all data]

Bruno, Moule, et al., 1989
Bruno, A.E.; Moule, D.C.; Steer, R.P., Decay dynamics of the lowest triplet and lowest excited singlet states of thioacetaldehyde and thioacetone, J. Photochem. Photobiol. A: Chem., 1989, 46, 2, 169, https://doi.org/10.1016/1010-6030(89)80003-6 . [all data]

Notes

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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