Chloromethyl cyanide

• Formula: C₂H₂ClN
• Molecular weight: 75.497
• IUPAC Standard InChI: InChI=1S/C2H2ClN/c3-1-2-4/h1H2 Copy

  
• IUPAC Standard InChIKey: RENMDAKOXSCIGH-UHFFFAOYSA-N Copy
• 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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• Information on this page:
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase ion energetics 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 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

Ionization energy determinations

De-protonation reactions

C₂HClN^- +  =

By formula: C₂HClN^- + H⁺ = C₂H₂ClN

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.

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]

Notes

Go To: Top, Gas phase ion energetics data, 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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