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Allyl chloride

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Gas phase 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-5.6kJ/molIonTraeger, 1984 

Condensed phase 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: Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
125.1298.von Reis, 1881T = 289 to 334 K.

Phase change 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil318.2 ± 0.7KAVGN/AAverage of 12 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus138.65KN/ATimmermans, 1952Uncertainty assigned by TRC = 0.5 K; TRC
Tfus136.75KN/ATimmermans, 1911Uncertainty assigned by TRC = 0.4 K; TRC
Quantity Value Units Method Reference Comment
Deltavap29.9kJ/molN/ADjkyj, Paulech, et al., 1960Based on data from 276. - 320. K.; AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
33.1218.AStephenson and Malanowski, 1987Based on data from 203. - 318. K.; AC
30.0301.N/AIoffe and Yamp'olskaya, 1944Based on data from 286. - 317. K. See also Boublik, Fried, et al., 1984.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
286.4 - 317.12.24083365.121-154.919Joffe and Jampolskaja, 1944Coefficents calculated by NIST from author's data.

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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 as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

C3H4Cl- + Hydrogen cation = Allyl chloride

By formula: C3H4Cl- + H+ = C3H5Cl

Quantity Value Units Method Reference Comment
Deltar1590. ± 17.kJ/molG+TSDahlke and Kass, 1991gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B
Deltar1571. ± 8.8kJ/molG+TSPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF, near tBuOH; B
Quantity Value Units Method Reference Comment
Deltar1559. ± 17.kJ/molIMRBDahlke and Kass, 1991gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B
Deltar1540. ± 8.4kJ/molIMRBPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF, near tBuOH; B

Allyl chloride + 2Dimethylamine = N-Allyl-N,N-dimethylamine + Dimethylamine hydrochloride

By formula: C3H5Cl + 2C2H7N = C5H11N + C2H8ClN

Quantity Value Units Method Reference Comment
Deltar-82.6 ± 0.4kJ/molCmBeldie, Aelenei, et al., 1982liquid phase; ALS

Allyl chloride = 1-Propene, 1-chloro-

By formula: C3H5Cl = C3H5Cl

Quantity Value Units Method Reference Comment
Deltar-9.96 ± 0.42kJ/molCisoAbell and Adolf, 1969gas phase; HBr catalyst; ALS

1-Propene, 1-chloro-, (Z)- = Allyl chloride

By formula: C3H5Cl = C3H5Cl

Quantity Value Units Method Reference Comment
Deltar15. ± 0.8kJ/molEqkAlfassi, Golden, et al., 1973liquid phase; ALS

1-Propene, 1-chloro- = Allyl chloride

By formula: C3H5Cl = C3H5Cl

Quantity Value Units Method Reference Comment
Deltar11. ± 0.8kJ/molEqkAlfassi, Golden, et al., 1973liquid phase; ALS

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/kg*bar)
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/kg*bar) d(ln(kH))/d(1/T) (K) Method Reference Comment
0.11 QN/A missing citation give several references for the Henry's law constants but don't assign them to specific species.
0.092 VN/A 
0.11 VN/A 

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:
L - Sharon G. Lias

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

Quantity Value Units Method Reference Comment
IE (evaluated)10.05 ± 0.01eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
10.05PITraeger, 1984, 2LBLHLM
9.9PEBieri, Asbrink, et al., 1982LBLHLM
10.04 ± 0.01PIBuff, Parr, et al., 1981LLK
10.05PEMines and Thompson, 1973LLK
10.05PEBieri, Asbrink, et al., 1982Vertical value; LBLHLM
10.34PEZverev and Ermolaeva, 1981Vertical value; LLK
10.20PEWorrell, 1974Vertical value; LLK
10.34PESchmidt and Schweig, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+13.37 ± 0.08?PIBuff, Parr, et al., 1981LLK
C3H5+11.04ClPITraeger, 1984, 2LBLHLM
C3H5+11.05 ± 0.04ClPIBuff, Parr, et al., 1981LLK

De-protonation reactions

C3H4Cl- + Hydrogen cation = Allyl chloride

By formula: C3H4Cl- + H+ = C3H5Cl

Quantity Value Units Method Reference Comment
Deltar1590. ± 17.kJ/molG+TSDahlke and Kass, 1991gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B
Deltar1571. ± 8.8kJ/molG+TSPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF, near tBuOH; B
Quantity Value Units Method Reference Comment
Deltar1559. ± 17.kJ/molIMRBDahlke and Kass, 1991gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B
Deltar1540. ± 8.4kJ/molIMRBPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF, near tBuOH; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


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 NIST Mass Spectrometry Data Center, 1998.
NIST MS number 291300

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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

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryPetrocol DH516.White, Hackett, et al., 1992100. m/0.25 mm/0.5 «mu»m, He, 1. K/min; Tstart: 30. C; Tend: 220. C

Normal alkane RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedSynachrom150.495.Dufka, Malinsky, et al., 1971Helium, Synachrom (60-80 mesh); Column length: 1.5 m
PackedSynachrom150.500.Dufka, Malinsky, et al., 1971Helium, Synachrom (60-80 mesh); Column length: 1.5 m

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryOV-101526.Zenkevich, 200525. m/0.20 mm/0.10 «mu»m, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C
CapillarySE-54498.Huang, Liang, et al., 199636. m/0.25 mm/0.25 «mu»m, 5. K/min; Tstart: 35. C; Tend: 240. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxanes526.Zenkevich and Chupalov, 1996Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, Notes

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

Traeger, 1984
Traeger, J.C., A study of the allyl cation thermochemistry by photoionization mass spectrometry, Int. J. Mass Spectrom. Ion Processes, 1984, 58, 259-271. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Timmermans, 1952
Timmermans, J., Freezing points of organic compounds. VVI New determinations., Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]

Timmermans, 1911
Timmermans, J., Researches on the freezing point of organic liquid compounds, Bull. Soc. Chim. Belg., 1911, 25, 300. [all data]

Djkyj, Paulech, et al., 1960
Djkyj, J.; Paulech, J.; Seprakova, M., Chem. Zvesti, 1960, 14, 327. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Ioffe and Yamp'olskaya, 1944
Ioffe, I.I.; Yamp'olskaya, E.S., Zh. Prikl. Khim. (S.-Peterburg), 1944, 17, 527. [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Joffe and Jampolskaja, 1944
Joffe, J.J.; Jampolskaja, E.S., On the Pressure of the Saturated Vapour of Allyl Chloride, Zh. Prikl. Khim. (Leningrad), 1944, 17, 527-528. [all data]

Dahlke and Kass, 1991
Dahlke, G.D.; Kass, S.R., Substituent Effects in the Gas Phase - 1-Substituted Allyl Anions, J. Am. Chem. Soc., 1991, 113, 15, 5566, https://doi.org/10.1021/ja00015a008 . [all data]

Poutsma, Nash, et al., 1997
Poutsma, J.C.; Nash, J.J.; Paulino, J.A.; Squires, R.R., Absolute Heats of Formation of Phenylcarbene and Vinylcarbene, J. Am. Chem. Soc., 1997, 119, 20, 4686, https://doi.org/10.1021/ja963918s . [all data]

Beldie, Aelenei, et al., 1982
Beldie, C.; Aelenei, N.; Onu, A.; Nemtoi, G., Thermochemical characterization of the reactions involved in the allyldimethylamine synthesis, Rev. Chim. (Bucharest), 1982, 33, 917-919. [all data]

Abell and Adolf, 1969
Abell, P.I.; Adolf, P.K., HBr catalyzed photoisomerization of allyl halides, J. Chem. Thermodyn., 1969, 1, 333-338. [all data]

Alfassi, Golden, et al., 1973
Alfassi, Z.B.; Golden, D.M.; Benson, S.W., The thermochemistry of the isomerization of 3-halopropenes (allyl halides) to 1-halopropenes; entropy and enthalpy of formation contribution of the Cd-(H)(X) group, J. Chem. Thermodyn., 1973, 5, 411-420. [all data]

Traeger, 1984, 2
Traeger, J.C., A study of the allyl cation thermochemistry by photoionization mass spectrometry, Int. J. Mass Spectrom. Ion Processes, 1984, 58, 259. [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]

Buff, Parr, et al., 1981
Buff, R.D.; Parr, A.C.; Jason, A.J., The photoionization of allyl chloride from onset to 20 eV, Int. J. Mass Spectrom. Ion Phys., 1981, 40, 31. [all data]

Mines and Thompson, 1973
Mines, G.W.; Thompson, H.W., Photoelectron spectra of vinyl and allyl halides, Spectrochim. Acta Part A, 1973, 29, 1377. [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]

Worrell, 1974
Worrell, C.W., The photoelectron and absorption spectra of allyl halides, J. Electron Spectrosc. Relat. Phenom., 1974, 3, 359. [all data]

Schmidt and Schweig, 1973
Schmidt, H.; Schweig, A., Semiquantitative proof of hyperconjugation, Angew. Chem. Int. Ed. Engl., 1973, 12, 307. [all data]

White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S., Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane, J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211 . [all data]

Dufka, Malinsky, et al., 1971
Dufka, O.; Malinsky, J.; Vladyka, J., Sorpcni materialy pro plynovou chromatographii - III, Chemicky promysl., 1971, 21/46, 9, 459-463. [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Huang, Liang, et al., 1996
Huang, C.; Liang, H.; Han, S., The analysis of organic compounds in waste water by gas extraction/thermal desorption/gas chromatography-mass spectrometry, Chin. J. Chromatogr., 1996, 14, 6, 421-424. [all data]

Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A., New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments, Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References