Chloromethyl cyanide
- Formula: C2H2ClN
- Molecular weight: 75.497
- IUPAC Standard InChIKey: RENMDAKOXSCIGH-UHFFFAOYSA-N
- CAS Registry Number: 107-14-2
- 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: Chloroacetonitrile; Acetonitrile, chloro-; α-Chloroacetonitrile; Chloracetonitrile; Monochloroacetonitrile; Monochloromethyl cyanide; 2-Chloroacetonitrile; CH2ClCN; Chloroethanenitrile; USAF KF-5; UN 2668; Acetonitrile, 2-chloro-; NSC 6180
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Gas phase ion energetics data
Go To: Top, Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 745.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 715.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
11.95 ± 0.01 | PE | Staley, Kleckner, et al., 1976 | LLK |
11.98 | PE | Botter, Gounelle, et al., 1977 | Vertical value; LLK |
12.05 | PE | Lake and Thompson, 1970 | Vertical value; RDSH |
De-protonation reactions
C2HClN- + =
By formula: C2HClN- + H+ = C2H2ClN
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1497. ± 9.2 | kJ/mol | G+TS | Poutsma, Upshaw, et al., 2002 | gas phase; B |
ΔrH° | 1457. ± 29. | kJ/mol | EIAE | Hacaloglu, Suzer, et al., 1988 | gas phase; From ClCH2CN. ΔGacid more likely to be ca. 360 - JEB.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1464. ± 8.4 | kJ/mol | IMRB | Poutsma, Upshaw, et al., 2002 | gas phase; B |
ΔrG° | 1429. ± 33. | kJ/mol | H-TS | Hacaloglu, Suzer, et al., 1988 | gas phase; From ClCH2CN. ΔGacid more likely to be ca. 360 - JEB.; B |
Gas Chromatography
Go To: Top, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apiezon L | 100. | 606. | Brown, Chapman, et al., 1968 | N2, DCMS-treated Chromosorb W; Column length: 2.3 m |
References
Go To: Top, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Staley, Kleckner, et al., 1976
Staley, R.H.; Kleckner, J.E.; Beauchamp, J.L.,
Relationship between orbital ionization energies and molecular properties. Proton affinities and photoelectron spectra of nitriles,
J. Am. Chem. Soc., 1976, 98, 2081. [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]
Lake and Thompson, 1970
Lake, R.F.; Thompson, H.,
The photoelectron spectra of some molecules containing the C N group,
Proc. Roy. Soc. (London), 1970, A317, 187. [all data]
Poutsma, Upshaw, et al., 2002
Poutsma, J.C.; Upshaw, S.D.; Squires, R.R.; Wenthold, P.G.,
Absolute heat of formation and singlet-triplet splitting for HCCN,
J. Phys. Chem. A, 2002, 106, 6, 1067-1073, https://doi.org/10.1021/jp013653q
. [all data]
Hacaloglu, Suzer, et al., 1988
Hacaloglu, J.; Suzer, S.; Oster, T.; Illenberger, E.,
Negative Ion Formation in Fluoroacetonitrile and Chloroacetonitrile following Low Energy Electron Impact,
Chem. Phys. Lett., 1988, 153, 2-3, 268, https://doi.org/10.1016/0009-2614(88)85224-2
. [all data]
Brown, Chapman, et al., 1968
Brown, I.; Chapman, I.L.; Nicholson, G.J.,
Gas chromatography of polar solutes in electron acceptor stationary phases,
Aust. J. Chem., 1968, 21, 5, 1125-1141, https://doi.org/10.1071/CH9681125
. [all data]
Notes
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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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