(Trifluoromethyl)acetylene
- Formula: C3HF3
- Molecular weight: 94.0352
- IUPAC Standard InChI: InChI=1S/C3HF3/c1-2-3(4,5)6/h1H
- IUPAC Standard InChIKey: PRDFNJUWGIQQBW-UHFFFAOYSA-N
- CAS Registry Number: 661-54-1
- 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. - Other names: 1-Propyne, 3,3,3-trifluoro-; Propyne, 3,3,3-trifluoro-; 1,1,1-Trifluoropropyne; 3,3,3-Trifluoro-1-propyne; 3,3,3-Trifluoropropyne; CF3C≡CH
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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
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
C3F3- + =
By formula: C3F3- + H+ = C3HF3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 355.1 ± 2.1 | kcal/mol | G+TS | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 347.4 ± 2.0 | kcal/mol | IMRE | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, Vibrational and/or electronic energy levels, References, Notes
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 |
|---|---|---|---|
| 11.96 ± 0.02 | PE | Bieri, Heilbronner, et al., 1979 | LLK |
| 11.83 | PE | Cullen, Frost, et al., 1972 | LLK |
De-protonation reactions
C3F3- + =
By formula: C3F3- + H+ = C3HF3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 355.1 ± 2.1 | kcal/mol | G+TS | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 347.4 ± 2.0 | kcal/mol | IMRE | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Vibrational and/or electronic energy levels
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Takehiko Shimanouchi
Symmetry: C3ν Symmetry Number σ = 3
| Sym. | No | Approximate | Selected Freq. | Infrared | Raman | Comments | ||||
|---|---|---|---|---|---|---|---|---|---|---|
| Species | type of mode | Value | Rating | Value | Phase | Value | Phase | |||
| a1 | 1 | CH str | 3327 | B | 3327.3 S | gas | 3316 p | liq. | ||
| a1 | 2 | C≡C str | 2165 | C | 2165.4 S | gas | 2156 p | liq. | FR(ν4+ν6+ν10) | |
| a1 | 3 | CF3 s-str | 1253 | B | 1253.2 VS | gas | 1250 | liq. | ||
| a1 | 4 | C-C str | 812 | B | 811.9 W | gas | 810 p | liq. | ||
| a1 | 5 | CF3 s-deform | 536 | B | 536.1 M | gas | 537 p | liq. | ||
| e | 6 | CF3 d-str | 1179 | B | 1179.2 VS | gas | 1155 dp | liq. | ||
| e | 7 | CH bend | 686 | B | 685.5 S | gas | 696 dp | liq. | ||
| e | 8 | CF3 d-deform | 612 | B | 611.9 M | gas | 606 dp | liq. | ||
| e | 9 | CF3 rock | 453 | B | 453.0 M | gas | 445 dp | liq. | ||
| e | 10 | CCC bend | 171 | B | 171 M | gas | 170 dp | liq. | ||
Source: Shimanouchi, 1972
Notes
| VS | Very strong |
| S | Strong |
| M | Medium |
| W | Weak |
| p | Polarized |
| dp | Depolarized |
| FR | Fermi resonance with an overtone or a combination tone indicated in the parentheses. |
| B | 1~3 cm-1 uncertainty |
| C | 3~6 cm-1 uncertainty |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D.,
The Nature and Analysis of Substituent Effects,
Prog. Phys. Org. Chem., 1987, 16, 1. [all data]
Bieri, Heilbronner, et al., 1979
Bieri, G.; Heilbronner, E.; Hornung, V.; Kloster-Jensen, E.; Maier, J.P.; Thommen, F.; von Niessen, W.,
Electronic states of substituted haloacetylene and cyanoacetylene radical cations,
Chem. Phys., 1979, 36, 1. [all data]
Cullen, Frost, et al., 1972
Cullen, W.R.; Frost, D.C.; Leeder, W.R.,
The ultraviolet and photoelectron spectra of some unsaturated fluorocarbon derivatives,
J. Fluorine Chem., 1972, 1, 227. [all data]
Shimanouchi, 1972
Shimanouchi, T.,
Tables of Molecular Vibrational Frequencies Consolidated Volume II,
J. Phys. Chem. Ref. Data, 1972, 6, 3, 993-1102. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, 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
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