Dichloromethylene

• Formula: CCl₂
• Molecular weight: 82.917
• IUPAC Standard InChI: InChI=1S/CCl2/c2-1-3 Copy

  
• IUPAC Standard InChIKey: PFBUKDPBVNJDEW-UHFFFAOYSA-N Copy
• CAS Registry Number: 1605-72-7
• 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.
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Gas phase ion energetics data
  • Vibrational and/or electronic energy levels
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Gas phase ion energetics data, Vibrational and/or electronic energy levels, References, Notes

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

Gas Phase Heat Capacity (Shomate Equation)

C_p° = A + B*t + C*t² + D*t³ + E/t²
H° − H°_298.15= A*t + B*t²/2 + C*t³/3 + D*t⁴/4 − E/t + F − H
S° = A*ln(t) + B*t + C*t²/2 + D*t³/3 − E/(2*t²) + G
    C_p = heat capacity (J/mol*K)
    H° = standard enthalpy (kJ/mol)
    S° = standard entropy (J/mol*K)
    t = temperature (K) / 1000.

View plot Requires a JavaScript / HTML 5 canvas capable browser.

View table.

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Vibrational and/or electronic energy levels, 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:
LL - Sharon G. Lias and Joel F. Liebman
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

View reactions leading to CCl₂⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

Vibrational and/or electronic energy levels

Go To: Top, Gas phase thermochemistry data, 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: Marilyn E. Jacox

State:   A

State:   a

State:   X

Additional references: Jacox, 1994, page 99; Jacox, 2003, page 138; Ibuki, Hiraya, et al., 1989; Fujitake and Hirota, 1989; Hansen, Mader, et al., 2001; Pancur, Brendel, et al., 2005

Notes

References

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

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

Chase, 1998
Chase, M.W., Jr., NIST-JANAF Themochemical Tables, Fourth Edition, J. Phys. Chem. Ref. Data, Monograph 9, 1998, 1-1951. [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]

Wren, Vogelhuber, et al., 2009
Wren, S.W.; Vogelhuber, K.M.; Ervin, K.M.; Lineberger, W.C., The photoelectron spectrum of CCl2-: the convergence of theory and experiment after a decade of debate, Phys. Chem. Chem. Phys., 2009, 11, 23, 4745-4753, https://doi.org/10.1039/b822690c . [all data]

Born, Ingemann, et al., 2000
Born, M.; Ingemann, S.; Nibbering, N.M.M., Thermochemical properties of halogen-substituted methanes, methyl radicals, and carbenes in the gas phase, Int. J. Mass Spectrom., 2000, 194, 2-3, 103-113, https://doi.org/10.1016/S1387-3806(99)00125-6 . [all data]

Schwartz, Davico, et al., 1999
Schwartz, R.L.; Davico, G.E.; Ramond, T.M.; Lineberger, W.C., Singlet-triplet splittings in CX2 (X = F, Cl, Br, I) dihalocarbenes via negative ion photoelectron spectroscopy, J. Phys. Chem. A, 1999, 103, 41, 8213-8221, https://doi.org/10.1021/jp992214c . [all data]

Barden and Schaeffer, 2000
Barden, C.J.; Schaeffer, H.F., III, The Singlet-Triplet Energy Separation in Dichlorocarbene: a Surprising Difference Between Theory and Experiment, J. Chem. Phys., 2000, 112, 15, 6515-6516, https://doi.org/10.1063/1.481601 . [all data]

Dyke, Lee, et al., 2005
Dyke, J.M.; Lee, E.P.F.; Mok, D.K.W.; Chau, F.T., A combined ab initio/Franck-Condon study of the A-X single-vibronic-level emission spectrum of CCl2 and the photodetachment spectrum of CCl2-, ChemPhysChem, 2005, 6, 10, 2046-2059, https://doi.org/10.1002/cphc.200500194 . [all data]

Murray, Leopold, et al., 1988
Murray, K.K.; Leopold, D.G.; Miller, T.M.; Lineberger, W.C., Photoelectron Spectroscopy of the Halocarbene Anions HCF^-, HCCl^-, HCBr^-, HCI^-, CF₂^-, and CCl₂^-, J. Chem. Phys., 1988, 89, 9, 5442, https://doi.org/10.1063/1.455596 . [all data]

Dispert and Lacmann, 1978
Dispert, H.; Lacmann, K., Negative ion formation in collisions between potassium and fluoro- and chloromethanes: Electron affinities and bond dissociation energies, Int. J. Mass Spectrom. Ion Phys., 1978, 28, 49. [all data]

Scheunemann, Illenberger, et al., 1980
Scheunemann, H.U.; Illenberger, E.; Baumgartel, H., Dissociative electron attachment to CCl₄, CHCl₃, CH₂Cl₂, and CH₃Cl, Ber. Bunsen-Ges. Phys. Chem., 1980, 84, 580. [all data]

Kohn, Robles, et al., 1993
Kohn, D.W.; Robles, E.S.J.; Logan, C.F.; Chen, P., Photoelectron spectrum, ionization potential, and heat of formation of CCl₂, J. Phys. Chem., 1993, 97, 4936. [all data]

Shapiro and Lossing, 1968
Shapiro, J.S.; Lossing, F.P., Free radicals by mass spectrometry. XXXVII. The ionization potential and heat of formation of dichlorocarbene, J. Phys. Chem., 1968, 72, 1552. [all data]

Blanchard and LeGoff, 1957
Blanchard, L.P.; LeGoff, P., Mass spectrometric study of the species CS, SO, and CCl₂ produced in primary heterogeneous reactions, Can. J. Chem., 1957, 35, 89. [all data]

Huie, Long, et al., 1977
Huie, R.E.; Long, N.J.T.; Thrush, B.A., Laser induced fluorescence of CFCl and CCl2 in the gas phase, Chem. Phys. Lett., 1977, 51, 2, 197, https://doi.org/10.1016/0009-2614(77)80383-7 . [all data]

Kiefer, Siegel, et al., 1978
Kiefer, R.; Siegel, A.; Schultz, A., Two chemiluminescence studies of the reaction Ba + CCl4 → BaCl2 + CCl2(Ã), Chem. Phys. Lett., 1978, 59, 2, 298, https://doi.org/10.1016/0009-2614(78)89099-X . [all data]

Tiee, Wampler, et al., 1979
Tiee, J.J.; Wampler, F.B.; Rice, W.W., Laser-induced fluorescence excitation spectra of CCl2 and CFCI radicals in the gas phase, Chem. Phys. Lett., 1979, 65, 3, 425, https://doi.org/10.1016/0009-2614(79)80264-X . [all data]

Predmore, Murray, et al., 1984
Predmore, D.A.; Murray, A.M.; Harmony, M.D., Laser-excitation spectrum of gas-phase CCl2, Chem. Phys. Lett., 1984, 110, 2, 173, https://doi.org/10.1016/0009-2614(84)80170-0 . [all data]

Ibuki, Takahashi, et al., 1986
Ibuki, T.; Takahashi, N.; Hiraya, A.; Shobatake, K., CCl2(A 1B1) radical formation in VUV photolyses of CCl4 and CBrCl3, J. Chem. Phys., 1986, 85, 10, 5717, https://doi.org/10.1063/1.451532 . [all data]

Choe, Tanner, et al., 1989
Choe, J.-I.; Tanner, S.R.; Harmony, M.D., Laser-excitation spectrum and structure of CCl2 in a free-jet expansion from a heated nozzle, J. Mol. Spectrosc., 1989, 138, 2, 319, https://doi.org/10.1016/0022-2852(89)90001-5 . [all data]

Clouthier and Karolczak, 1989
Clouthier, D.J.; Karolczak, J., Pyrolysis jet spectroscopy: rotationally resolved electronic spectrum of dichlorocarbene, J. Phys. Chem., 1989, 93, 22, 7542, https://doi.org/10.1021/j100359a003 . [all data]

Clouthier and Karolczak, 1991
Clouthier, D.J.; Karolczak, J., A pyrolysis jet spectroscopic study of the rotationally resolved electronic spectrum of dichlorocarbene, J. Chem. Phys., 1991, 94, 1, 1, https://doi.org/10.1063/1.460378 . [all data]

Lu, Chen, et al., 1991
Lu, Q.; Chen, Y.; Wang, D.; Zhang, Y.; Yu, S.; Chen, C.; Koshi, M.; Matsui, H.; Koda, S.; Ma, X., Laser-induced fluorescence excitation spectrum of CCl2 cooled in a supersonic free jet, Chem. Phys. Lett., 1991, 178, 5-6, 517, https://doi.org/10.1016/0009-2614(91)87012-Z . [all data]

Liu, Lee, et al., 2003
Liu, M.-L.; Lee, C.-L.; Bezant, A.; Tarczay, G.; Clark, R.J.; Miller, T.A.; Chang, B.-C., Dispersed fluorescence spectra of the CCl2 Ã--X vibronic bands, Phys. Chem. Chem. Phys., 2003, 5, 7, 1352, https://doi.org/10.1039/b300637a . [all data]

Guss, Richmond, et al., 2005
Guss, J.S.; Richmond, C.A.; Nauta, K.; Kable, S.H., Laser-induced fluorescence excitation and dispersed fluorescence spectroscopy of the «65533»(1B1)?X?(1A1) transition of dichlorocarbene, Phys. Chem. Chem. Phys., 2005, 7, 1, 100, https://doi.org/10.1039/b413391a . [all data]

Mukarakate, Mishchenko, et al., 2006
Mukarakate, C.; Mishchenko, Y.; Brusse, D.; Tao, C.; Reid, S.A., Probing spin?orbit mixing and the singlet?triplet gap in dichloromethylene via?Ka-sorted emission spectra, Phys. Chem. Chem. Phys., 2006, 8, 37, 4320, https://doi.org/10.1039/b610582c . [all data]

Richmond, Tao, et al., 2008
Richmond, C.; Tao, C.; Mukarakate, C.; Fan, H.; Nauta, K.; Schmidt, T.W.; Kable, S.H.; Reid, S.A., Unraveling the A, J. Phys. Chem. A, 2008, 112, 45, 11355, https://doi.org/10.1021/jp806944q . [all data]

Milligan and Jacox, 1967
Milligan, D.E.; Jacox, M.E., Matrix-Isolation Study of the Reaction of Carbon Atoms with Chlorine. The Electronic and Vibrational Spectra of the Free Radical CCl2, J. Chem. Phys., 1967, 47, 2, 703, https://doi.org/10.1063/1.1711942 . [all data]

Jacox and Milligan, 1970
Jacox, M.E.; Milligan, D.E., Matrix-Isolation Study of the Vacuum-Ultraviolet Photolysis of Methyl Chloride and Methylene Chloride. Infrared and Ultraviolet Spectra of the Free Radicals CCl, H2CCl, and CCl2, J. Chem. Phys., 1970, 53, 7, 2688, https://doi.org/10.1063/1.1674392 . [all data]

Shirk, 1971
Shirk, J.S., Laser Excited Fluorescence of CCl2, J. Chem. Phys., 1971, 55, 7, 3608, https://doi.org/10.1063/1.1676629 . [all data]

Tevault and Andrews, 1975
Tevault, D.E.; Andrews, L., Laser-induced fluorescence spectrum of argon matrix-isolated dichlorocarbene, J. Mol. Spectrosc., 1975, 54, 1, 110, https://doi.org/10.1016/0022-2852(75)90012-0 . [all data]

Bondybey, 1977
Bondybey, V.E., Emission and excitation spectra of CCl2 in solid argon, J. Mol. Spectrosc., 1977, 64, 2, 180, https://doi.org/10.1016/0022-2852(77)90257-0 . [all data]

Wren, Vogelhuber, et al., 2009, 2
Wren, S.W.; Vogelhuber, K.M.; Ervin, K.M.; Lineberger, W.C., The photoelectron spectrum of CCl2-: the convergence of theory and experiment after a decade of debate, Phys. Chem. Chem. Phys., 2009, 11, 23, 4745, https://doi.org/10.1039/b822690c . [all data]

Schwartz, Davico, et al., 1999, 2
Schwartz, R.L.; Davico, G.E.; Ramond, T.M.; Lineberger, W.C., Singlet-Triplet Splittings in CX, J. Phys. Chem. A, 1999, 103, 41, 8213, https://doi.org/10.1021/jp992214c . [all data]

Lugez, Jacox, et al., 1998
Lugez, C.L.; Jacox, M.E.; Johnson, R.D., III, Matrix isolation study of the interaction of excited neon atoms with CCl[sub 4]: Infrared spectra of the ion products and of Cl[sub 2]CCl••Cl, J. Chem. Phys., 1998, 109, 17, 7147, https://doi.org/10.1063/1.477397 . [all data]

Andrews, 1968
Andrews, L., Infrared Spectrum of Dichlorocarbene in Solid Argon, J. Chem. Phys., 1968, 48, 3, 979, https://doi.org/10.1063/1.1668853 . [all data]

Fridgen, Zhang, et al., 2000
Fridgen, T.D.; Zhang, X.K.; Parnis, J.M.; March, R.E., Isomerization and Fragmentation Products of CH, J. Phys. Chem. A, 2000, 104, 16, 3487, https://doi.org/10.1021/jp993162u . [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, 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]

Ibuki, Hiraya, et al., 1989
Ibuki, T.; Hiraya, A.; Shobatake, K., Photoabsorption spectrum and CCl2(Ã 1B1) radical formation in the VUV excitation of C2Cl6, Chem. Phys. Lett., 1989, 157, 6, 521, https://doi.org/10.1016/S0009-2614(89)87403-2 . [all data]

Fujitake and Hirota, 1989
Fujitake, M.; Hirota, E., The millimeter- and submillimeter-wave spectrum of dichlorocarbene CCl2: Electronic structure estimated from the nuclear quadrupole coupling constants, J. Chem. Phys., 1989, 91, 6, 3426, https://doi.org/10.1063/1.456916 . [all data]

Hansen, Mader, et al., 2001
Hansen, N.; Mader, H.; Temps, F., The rotational spectrum of dichlorocarbene, C35Cl2, observed by molecular beam-Fourier transform microwave spectroscopy, Phys. Chem. Chem. Phys., 2001, 3, 1, 50, https://doi.org/10.1039/b007492f . [all data]

Pancur, Brendel, et al., 2005
Pancur, T.; Brendel, K.; Hansen, N.; Madur, H.; Markov, V.; Temps, F., Microwave spectra of the 35Cl and 37Cl isotopomers of dichloromethylene: Nuclear quadrupole-, spin--rotation-, and nuclear shielding constants from the hyperfine structures of rotational lines, J. Mol. Spectrosc., 2005, 232, 2, 375, https://doi.org/10.1016/j.jms.2005.04.013 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, References

• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  S°gas,1 bar	Entropy of gas at standard conditions (1 bar)
  ΔfH°gas	Enthalpy of formation of gas at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.