1-Propyne, 3-chloro-
- Formula: C3H3Cl
- Molecular weight: 74.509
- IUPAC Standard InChI: InChI=1S/C3H3Cl/c1-2-3-4/h1H,3H2
- IUPAC Standard InChIKey: LJZPPWWHKPGCHS-UHFFFAOYSA-N
- CAS Registry Number: 624-65-7
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Propyne, 3-chloro-; Propargyl chloride; 2-Propynyl chloride; 3-Chloro-1-propyne; 3-Chloropropyne; CH2ClC≡CH
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Gas phase ion energetics data
Go To: Top, 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
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
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.68 | EI | Holmes and Lossing, 1979 | LLK |
| 10.7 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
| 10.76 | PE | Zverev and Ermolaeva, 1981 | Vertical value; LLK |
| 10.76 | PE | Andreocci, Bitchev, et al., 1979 | Vertical value; LLK |
| 10.76 | PE | Botter, Gounelle, et al., 1977 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C3H3+ | 11.00 | Cl | EI | Holmes and Lossing, 1979 | LLK |
De-protonation reactions
C3H2Cl- + =
By formula: C3H2Cl- + H+ = C3H3Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 368.0 ± 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° | 360.3 ± 2.0 | kcal/mol | IMRE | Taft and Topsom, 1987 | gas 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.
Holmes and Lossing, 1979
Holmes, J.L.; Lossing, F.P.,
The reactivity of [C3H3+] ions; a thermochemical study,
Can. J. Chem., 1979, 57, 249. [all data]
Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W.,
30.4-nm He(II) photoelectron spectra of organic molecules,
J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]
Zverev and Ermolaeva, 1981
Zverev, V.V.; Ermolaeva, L.V.,
Ionization potentials and intramolecular charge transfer. II. The photoelectron spectrum and electronic structure of trichloromethylbenzene,
Zh. Strukt. Khim., 1981, 22, 22. [all data]
Andreocci, Bitchev, et al., 1979
Andreocci, M.V.; Bitchev, P.; Carusi, P.; Furlani, A.,
Valence shell photoionization spectra of some substituted hydroxy-acetylenes. A tentative correlation with their cyclotrimerization reactions,
J. Electron Spectrosc. Relat. Phenom., 1979, 16, 25. [all data]
Botter, Gounelle, et al., 1977
Botter, R.; Gounelle, Y.; Henry, Y.; Jullien, J.; Menes, F.; Solgadi, D.,
Photoelectron spectra of halogeno-3-propynes (XCH2≡CH) and halogeno- methylcyanides (XCH2C≡N) and comments on the attribution of fluorine IP,
J. Electron Spectrosc. Relat. Phenom., 1977, 10, 393. [all data]
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]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy 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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