Allyl radical

• Formula: C₃H₅
• Molecular weight: 41.0718
• IUPAC Standard InChI: InChI=1S/C3H5/c1-3-2/h3H,1-2H2 Copy

  
• IUPAC Standard InChIKey: RMRFFCXPLWYOOY-UHFFFAOYSA-N Copy
• CAS Registry Number: 1981-80-2
• 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.
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• Information on this page:
  • Gas phase thermochemistry data
  • Gas phase ion energetics data
  • Vibrational and/or electronic energy levels
  • References
  • Notes
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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.

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:
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

View reactions leading to C₃H₅⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

Vibrational and/or electronic energy levels

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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: Marilyn E. Jacox

State:   8s

State:   7s

State:   6s

State:   5s

State:   4s

State:   3d

State:   D

State:   C

State:   B

State:   A

State:   X

Additional references: Jacox, 1994, page 372; Jacox, 1998, page 334; Jacox, 2003, page 356; Liu, Getty, et al., 1993; Schultz and Fischer, 1998

Notes

References

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, NIST Free Links, NIST Subscription Links, Notes

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

Tsang, 1996
Tsang, W., Heats of Formation of Organic Free Radicals by Kinetic Methods in Energetics of Organic Free Radicals, Martinho Simoes, J.A.; Greenberg, A.; Liebman, J.F., eds., Blackie Academic and Professional, London, 1996, 22-58. [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]

Wenthold, Polak, et al., 1996
Wenthold, P.G.; Polak, M.L.; Lineberger, W.C., Photoelectron Spectroscopy of the Allyl and 2-Methylallyl Anions, J. Phys. Chem., 1996, 100, 17, 6920, https://doi.org/10.1021/jp953401n . [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Oakes and Ellison, 1984
Oakes, J.M.; Ellison, G.B., Photoelectron spectroscopy of the allylic anion, J. Am. Chem. Soc., 1984, 106, 7734. [all data]

Zimmerman and Brauman, 1977
Zimmerman, A.H.; Brauman, J.I., Electron photodetachment from negative ions of C_2v symmetry. Electron affinities of allyl and cyanomethyl radicals, J. Am. Chem. Soc., 1977, 99, 3565. [all data]

Kagramanov, Ujszaszy, et al., 1983
Kagramanov, N.D.; Ujszaszy, K.; Tamas, J.; Mal'tsev, A.K.; Nefedov, O.M., Mass spectrometric detection of allylic and perfluorallylic free radicals and the determination of their ionization potentials, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1983, 7, 1531, In original 1683. [all data]

Griller and Lossing, 1981
Griller, D.; Lossing, F.P., On the thermochemistry of α-aminoalkyl radicals, J. Am. Chem. Soc., 1981, 103, 1586. [all data]

Houle and Beauchamp, 1978
Houle, F.A.; Beauchamp, J.L., Detection and investigation of allyl and benzyl radicals by photoelectron spectroscopy, J. Am. Chem. Soc., 1978, 100, 3290. [all data]

Lossing, 1971
Lossing, F.P., Free radicals by mass spectrometry. XLIII. Ionization potentials and ionic heats of formation for vinyl, allyl, and benzyl radicals, Can. J. Chem., 1971, 49, 357. [all data]

Pottie, Harrison, et al., 1961
Pottie, R.F.; Harrison, A.G.; Lossing, F.P., Free radicals by mass spectrometry. XXIV. Ionization potentials of cycloalkyl free radicals and cycloalkanes, J. Am. Chem. Soc., 1961, 83, 3204. [all data]

Wu, Li, et al., 2000
Wu, J.-C.; Li, R.; Chang, J.-L.; Chen, Y.-T., Rydberg states of the allyl radical observed by two-photon resonant ionization spectroscopy, J. Chem. Phys., 2000, 113, 17, 7286, https://doi.org/10.1063/1.1313560 . [all data]

Liang, Chen, et al., 2002
Liang, C.-W.; Chen, C.-C.; Wei, C.-Y.; Chen, Y.-T., Two-photon resonant ionization spectroscopy of the allyl-h[sub 5] and allyl-d[sub 5] radicals: Rydberg states and ionization energies, J. Chem. Phys., 2002, 116, 10, 4162, https://doi.org/10.1063/1.1450553 . [all data]

Blush, Minsek, et al., 1992
Blush, J.A.; Minsek, D.W.; Chen, P., Electronic spectrum of allyl and allyl-d5 radicals: the B[12A1] .rarw. X[12A2], C[22B1] .rarw. X[12A2], and D[12B2] .rarw. X[12A2] band systems, J. Phys. Chem., 1992, 96, 25, 10150, https://doi.org/10.1021/j100204a013 . [all data]

Getty, Liu, et al., 1992
Getty, J.D.; Liu, X.; Kelly, P.B., Vibronic coupling of the allyl radical excited states, J. Phys. Chem., 1992, 96, 25, 10155, https://doi.org/10.1021/j100204a014 . [all data]

Callear and Lee, 1968
Callear, A.B.; Lee, H.K., Electronic spectra of the free allyl radical and some of its simple derivatives, Trans. Faraday Soc., 1968, 64, 308, https://doi.org/10.1039/tf9686400308 . [all data]

Minsek, Blush, et al., 1992
Minsek, D.W.; Blush, J.A.; Chen, P., The 1 + 1 resonant multiphoton ionization spectrum of the allyl radical. Rotational structure in the ~C[22B1] .fwdarw. ~X[12A2] origin band, J. Phys. Chem., 1992, 96, 5, 2025, https://doi.org/10.1021/j100184a003 . [all data]

Minsek and Chen, 1993
Minsek, D.W.; Chen, P., The 1 + 1 and 2 + 2 resonant multiphoton ionization of allyl and allyl-dn (C3H5, C3H4D, C3HD4, and C3D5) radicals, J. Phys. Chem., 1993, 97, 50, 13375, https://doi.org/10.1021/j100152a050 . [all data]

Maier, Reisenauer, et al., 1983
Maier, G.; Reisenauer, H.P.; Rohde, B.; Dehnicke, K., IR-, UV- und ESR-Spektrum des Allylradikals in einer Argon-Matrix, Chem. Ber., 1983, 16, 2, 732, https://doi.org/10.1002/cber.19831160230 . [all data]

Hudgens and Dulcey, 1985
Hudgens, J.W.; Dulcey, C.S., Observation of the 3s 2A1 Rydberg states of allyl and 2-methylallyl radicals with multiphoton ionization spectroscopy, J. Phys. Chem., 1985, 89, 8, 1505, https://doi.org/10.1021/j100254a039 . [all data]

Sappey and Weisshaar, 1987
Sappey, A.D.; Weisshaar, J.C., Vibronic spectrum of cold, gas-phase allyl radicals by multiphoton ionization, J. Phys. Chem., 1987, 91, 14, 3731, https://doi.org/10.1021/j100298a004 . [all data]

Currie and Ramsay, 1966
Currie, C.L.; Ramsay, D.A., Electronic Absorption Spectrum and Dissociation Energy of the Allyl Radical, J. Chem. Phys., 1966, 45, 2, 488, https://doi.org/10.1063/1.1727594 . [all data]

Tonokura and Koshi, 2000
Tonokura, K.; Koshi, M., Absorption Spectrum and Cross Sections of the Allyl Radical Measured Using Cavity Ring-Down Spectroscopy: The à ← X Band, J. Phys. Chem. A, 2000, 104, 37, 8456, https://doi.org/10.1021/jp001129y . [all data]

Achkasova, Araki, et al., 2005
Achkasova, E.; Araki, M.; Denisov, A.; Maier, J.P., Rotational analysis of the electronic spectrum of the allyl radical, Mol. Phys., 2005, 103, 11-12, 1555, https://doi.org/10.1080/00268970500044830 . [all data]

Castiglione, Bach, et al., 2006
Castiglione, L.; Bach, A.; Chen, P., Spectroscopy and dynamics of A [2B1] allyl radical, Phys. Chem. Chem. Phys., 2006, 8, 22, 2591, https://doi.org/10.1039/b602412b . [all data]

Kim, Araki, et al., 2006
Kim, E.; Araki, M.; Chauhan, R.; Birza, P.; Maier, J.P., Electronic spectrum of the hydrocarbon cation, Mol. Phys.104, 2006, 104, 18, 2885, https://doi.org/10.1080/00268970600866694 . [all data]

Uy, Davis, et al., 1998
Uy, D.; Davis, S.; Nesbitt, D.J., High-resolution infrared spectroscopy of jet-cooled allyl radical (CH[sub 2]--CH--CH[sub 2]): In-phase (ν[sub 1]) and out-of-phase (ν[sub 13]) antisymmetric CH[sub 2] stretching vibrations, J. Chem. Phys., 1998, 109, 18, 7793, https://doi.org/10.1063/1.477425 . [all data]

DeSain, Thompson, et al., 1998
DeSain, J.D.; Thompson, R.I.; Sharma, S.D.; Curl, R.F., The rotationally resolved infrared spectrum of the ν[sub 1] stretch of the allyl radical, J. Chem. Phys., 1998, 109, 18, 7803, https://doi.org/10.1063/1.477426 . [all data]

Mal'tsev, Korolov, et al., 1982
Mal'tsev, A.K.; Korolov, V.A.; Nefedov, O.M., Izv. Akad. Nauk SSSR, 1982, Ser. Khim., 2415. [all data]

Mal'tsev, Korolev, et al., 1984
Mal'tsev, A.K.; Korolev, V.A.; Nefedov, O.M., Izv. Akad. Naul SSSR, 1984, Ser. Khim., 555. [all data]

Nandi, Arnold, et al., 2001
Nandi, S.; Arnold, P.A.; Carpenter, B.K.; Nimlos, M.R.; Dayton, D.C.; Ellison, G.B., Polarized Infrared Absorption Spectra of Matrix-Isolated Allyl Radicals, J. Phys. Chem. A, 2001, 105, 32, 7514, https://doi.org/10.1021/jp011163s . [all data]

Han, Utkin, et al., 2002
Han, J.-X.; Utkin, Yu.G.; Chen, H.-B.; Hunt, N.T.; Curl, R.F., High-resolution infrared spectra of jet-cooled allyl radical (CH[sub 2]--CH--CH[sub 2]): ν[sub 2], ν[sub 3], and ν[sub 14] C--H stretch vibrations, J. Chem. Phys., 2002, 116, 15, 6505, https://doi.org/10.1063/1.1459417 . [all data]

Getty, Burmeister, et al., 1991
Getty, J.D.; Burmeister, M.J.; Westre, S.G.; Kelly, P.B., Examination of allyl radical excited-state dynamics and ground-state vibrational frequencies by ultraviolet resonance Raman spectroscopy, M. Am. Chem. Soc., 1991, 113, 3, 801, https://doi.org/10.1021/ja00003a011 . [all data]

Getty and Kelly, 1992
Getty, J.D.; Kelly, P.B., Vibrational analysis of the X 2A2 state of the allyl radical, Chem. Phys., 1992, 168, 2-3, 357, https://doi.org/10.1016/0301-0104(92)87169-A . [all data]

Getty, Liu, et al., 1993
Getty, J.D.; Liu, X.; Kelly, P.B., Anomalous polarization: evidence for vibronic coupling in the allyl radical, Chem. Phys. Lett., 1993, 201, 1-4, 236, https://doi.org/10.1016/0009-2614(93)85062-S . [all data]

Holtzhauer, Cometta-Morini, et al., 1990
Holtzhauer, K.; Cometta-Morini, C.; Oth, J.F.M., Photochemical electrocyclization of the allyl radical into the cyclopropyl radical, J. Phys. Org. Chem., 1990, 3, 4, 219, https://doi.org/10.1002/poc.610030403 . [all data]

Hirota, Yamada, et al., 1992
Hirota, E.; Yamada, C.; Okunishi, M., Infrared diode laser spectroscopy of the allyl radical. The ν11 band, J. Chem. Phys., 1992, 97, 5, 2963, https://doi.org/10.1063/1.463037 . [all data]

Jacox and Milligan, 1974
Jacox, M.E.; Milligan, D.E., Matrix isolation study of the vacuum ultraviolet photolysis of allene and methylacetylene. Vibrational and electronic spectra of the species C3, C3H, C3H2, and C3H3, Chem. Phys., 1974, 4, 1, 45, https://doi.org/10.1016/0301-0104(74)80047-9 . [all data]

Huang and Graham, 1990
Huang, J.W.; Graham, W.R.M., Fourier transform infrared study of tricarbon hydride radicals trapped in Ar at 10 K, J. Chem. Phys., 1990, 93, 3, 1583, https://doi.org/10.1063/1.459137 . [all data]

DeSain and Curl, 1999
DeSain, J.D.; Curl, R.F., Rotational Analysis of ν13 of Allyl Radical, J. Mol. Spectrosc., 1999, 196, 2, 324, https://doi.org/10.1006/jmsp.1999.7868 . [all data]

Jacox, 1994
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules, American Chemical Society, Washington, DC, 1994, 464. [all data]

Jacox, 1998
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules: supplement A, J. Phys. Chem. Ref. Data, 1998, 27, 2, 115-393, https://doi.org/10.1063/1.556017 . [all data]

Jacox, 2003
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules: supplement B, J. Phys. Chem. Ref. Data, 2003, 32, 1, 1-441, https://doi.org/10.1063/1.1497629 . [all data]

Liu, Getty, et al., 1993
Liu, X.; Getty, J.D.; Kelly, P.B., Resonance Raman spectrum of the allyl-d5 radical and the force field analysis of the allyl radical, J. Chem. Phys., 1993, 99, 3, 1522, https://doi.org/10.1063/1.465320 . [all data]

Schultz and Fischer, 1998
Schultz, T.; Fischer, I., Time-resolved photoelectron spectroscopy of the allyl radical: The lifetimes of the ultraviolet bands, J. Chem. Phys., 1998, 109, 14, 5812, https://doi.org/10.1063/1.477203 . [all data]

Notes

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• Symbols used in this document:
  

  EA	Electron affinity
  ΔfH(+) ion,0K	Enthalpy of formation of positive ion at 0K
  ΔfH°gas	Enthalpy of formation of gas at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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