Chloromethyl cyanide

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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

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Individual Reactions

C2HClN- + Hydrogen cation = Chloromethyl cyanide

By formula: C2HClN- + H+ = C2H2ClN

Quantity Value Units Method Reference Comment
Δr1497. ± 9.2kJ/molG+TSPoutsma, Upshaw, et al., 2002gas phase
Δr1457. ± 29.kJ/molEIAEHacaloglu, Suzer, et al., 1988gas phase; From ClCH2CN. ΔGacid more likely to be ca. 360 - JEB.
Quantity Value Units Method Reference Comment
Δr1464. ± 8.4kJ/molIMRBPoutsma, Upshaw, et al., 2002gas phase
Δr1429. ± 33.kJ/molH-TSHacaloglu, Suzer, et al., 1988gas phase; From ClCH2CN. ΔGacid more likely to be ca. 360 - JEB.

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

Quantity Value Units Method Reference Comment
Proton affinity (review)745.7kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity715.1kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
11.95 ± 0.01PEStaley, Kleckner, et al., 1976LLK
11.98PEBotter, Gounelle, et al., 1977Vertical value; LLK
12.05PELake and Thompson, 1970Vertical value; RDSH

De-protonation reactions

C2HClN- + Hydrogen cation = Chloromethyl cyanide

By formula: C2HClN- + H+ = C2H2ClN

Quantity Value Units Method Reference Comment
Δr1497. ± 9.2kJ/molG+TSPoutsma, Upshaw, et al., 2002gas phase; B
Δr1457. ± 29.kJ/molEIAEHacaloglu, Suzer, et al., 1988gas phase; From ClCH2CN. ΔGacid more likely to be ca. 360 - JEB.; B
Quantity Value Units Method Reference Comment
Δr1464. ± 8.4kJ/molIMRBPoutsma, Upshaw, et al., 2002gas phase; B
Δr1429. ± 33.kJ/molH-TSHacaloglu, Suzer, et al., 1988gas phase; From ClCH2CN. ΔGacid more likely to be ca. 360 - JEB.; B

IR Spectrum

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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: Coblentz Society, Inc.

Condensed Phase Spectrum

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IR spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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Owner Copyright (C) 1987 by the Coblentz Society
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin SOUTHERN RESEARCH INSTITUTE
Source reference COBLENTZ NO. 7886
Date 1966/01/06
Name(s) chloroacetonitrile
State LIQUID (NEAT)
Instrument PERKIN-ELMER 521 (GRATING)
Instrument parameters FILTERS AT 3150, 2500, 2000, 1150, 700, 410. GRATING CHANGES: 2000, 630
Path length CAPILLARY (BETWEEN CsBr PLATES)
Resolution 2
Sampling procedure TRANSMISSION
Data processing DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY (ADJUSTED addcm-115-5-2)

This IR spectrum is from the Coblentz Society's evaluated infrared reference spectra collection.


Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-1496
NIST MS number 230381

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Gas Chromatography

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedApiezon L100.606.Brown, Chapman, et al., 1968N2, DCMS-treated Chromosorb W; Column length: 2.3 m

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

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]

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

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