Cyanomethylene
- Formula: C2HN
- Molecular weight: 39.0360
- IUPAC Standard InChI: InChI=1S/C2HN/c1-2-3/h1H
- IUPAC Standard InChIKey: SZICEGNEOSKVLO-UHFFFAOYSA-N
- CAS Registry Number: 2612-62-6
- 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: HCCN radical
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Reaction 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.
Data compiled by: John E. Bartmess
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
(CAS Reg. No. 74595-99-6 • 4294967295) +
= CAS Reg. No. 74595-99-6
By formula: (CAS Reg. No. 74595-99-6 • 4294967295C2HN) + C2HN = CAS Reg. No. 74595-99-6
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 43.8 ± 6.7 | kcal/mol | N/A | Poutsma, Upshaw, et al., 2002 | gas phase |
| ΔrH° | 43.7 ± 2.5 | kcal/mol | CIDT | Poutsma, Upshaw, et al., 2002 | gas phase |
Gas phase ion energetics data
Go To: Top, Reaction 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 compiled by: John E. Bartmess
View reactions leading to C2HN+ (ion structure unspecified)
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 2.003 ± 0.014 | LPES | Nimlos, Davico, et al., 2002 | |
| 1.883 ± 0.013 | LPES | Nimlos, Davico, et al., 2002 | |
| 2.01 ± 0.34 | D-EA | Matimba, Crabbendam, et al., 1992 | |
| 1.93 ± 0.34 | D-EA | Grabowski and Melly, 1987 | Between H2O2 and mCl-toluene |
| 0.80 ± 0.40 | EIAE | Heni and Illenberger, 1986 | From MeCN |
| >1.09997 | EIAE | Tsuda, Yokohata, et al., 1971 | From MeCN. G3MP2B3 calculations indicate an EA of ca. 2.0 eV. |
Vibrational and/or electronic energy levels
Go To: Top, Reaction 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: ?
| Energy (cm-1) |
Med. | Transition | λmin (nm) |
λmax (nm) |
References | ||
|---|---|---|---|---|---|---|---|
| Ar | 240 | 340 | Dendramis and Leroi, 1977 | ||||
State: a
| Energy (cm-1) |
Med. | Transition | λmin (nm) |
λmax (nm) |
References | ||
|---|---|---|---|---|---|---|---|
| To = 4115 ± 120 | gas | Nimlos, Davico, et al., 2002, 2 | |||||
| Vogelhuber, Wren, et al., 2011 | |||||||
| Vib. sym. |
No. | Approximate type of mode |
cm-1 | Med. | Method | References | |
|---|---|---|---|---|---|---|---|
| 2 | CN stretch | 1936 ± 40 | gas | PE | Vogelhuber, Wren, et al., 2011 | ||
State: X
| Vib. sym. |
No. | Approximate type of mode |
cm-1 | Med. | Method | References | |
|---|---|---|---|---|---|---|---|
| Σ+ | 1 | CH stretch | 3246.66 | gas | CC | Morter, Farhat, et al., 1993 | |
| 1 | CH stretch | 3229.4 | s | Ar | IR | Dendramis and Leroi, 1977 Maier, Reisenauer, et al., 1998 | |
| 1 | CH stretch | 3213.3 | N2 | IR | Maier, Reisenauer, et al., 1998 | ||
| 2 | CCN a-stretch | 1734.9 | s | Ar | IR | Dendramis and Leroi, 1977 Maier, Reisenauer, et al., 1998 | |
| 2 | CCN a-stretch | 1750.3 | N2 | IR | Maier, Reisenauer, et al., 1998 | ||
| 3 | CCN s-stretch | 1178.6 | w m | Ar | IR | Dendramis and Leroi, 1977 Maier, Reisenauer, et al., 1998 | |
| Π | 4 | H deform. | 383 ± 20 | gas | CC MW | Morter, Farhat, et al., 1993 McCarthy, Gottlieb, et al., 1995 | |
| 5 | Skel. deform. | 128.91 | gas | MW CC | McCarthy, Gottlieb, et al., 1995 Han, Hung, et al., 1999 Allen, Evenson, et al., 2001 Nimlos, Davico, et al., 2002, 2 | ||
Additional references: Jacox, 1994, page 156; Jacox, 1998, page 234; Jacox, 2003, page 185; Bernheim, Kempf, et al., 1965; Merer and Travis, 1965; Merer and Travis, 1966; Saito, Endo, et al., 1984; Brown, Saito, et al., 1990; Endo and Ohshima, 1993; Sun, Kosterev, et al., 1998; Jones, Sun, et al., 2001; Hung, Sun, et al., 2001
Notes
| w | Weak |
| m | Medium |
| s | Strong |
| o | Energy separation between the v = 0 levels of the excited and electronic ground states. |
References
Go To: Top, Reaction 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.
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]
Nimlos, Davico, et al., 2002
Nimlos, M.R.; Davico, G.; Geise, C.M.; Wenthold, P.G.; Lineberger, W.C.; Blanksby, S.J.; Hadad, C.M.; Petersso,
Photoelectron spectroscopy of HCCN- and HCNC- reveals the quasilinear triplet carbenes, HCCN and HCNC,
J. Chem. Phys., 2002, 117, 9, 4323-4339, https://doi.org/10.1063/1.1496473
. [all data]
Matimba, Crabbendam, et al., 1992
Matimba, H.E.K.; Crabbendam, A.M.; Ingemann, S.; Nibbering, N.M.M.,
Gas-phase Bimolecular Chemistry of the .-CHNC and .-CHCN Radical Anions,
Int. J. Mass Spectrom. Ion Proc., 1992, 114, 1-2, 85, https://doi.org/10.1016/0168-1176(92)85024-T
. [all data]
Grabowski and Melly, 1987
Grabowski, J.J.; Melly, S.J.,
Formation of carbene radical anions: Gas phase reaction of the atomic oxygen anion with organic neutrals,
Int. J. Mass Spectrom. Ion Processes, 1987, 81, 147. [all data]
Heni and Illenberger, 1986
Heni, M.; Illenberger, E.,
Electron attachment by saturated nitriles. Acrylonitrile (CH2H3CN), and benzonitrile (C6H5CN),
Int. J. Mass Spectrom. Ion Phys., 1986, 73, 127. [all data]
Tsuda, Yokohata, et al., 1971
Tsuda, S.; Yokohata, A.; Umaba, T.,
Measurement of negative ions formed by electron impact. VIII. Ionization efficiency curves of negative ions from methyl and ethyl cyanides,
Bull. Chem. Soc. Jpn., 1971, 44, 1486. [all data]
Dendramis and Leroi, 1977
Dendramis, A.; Leroi, G.E.,
Matrix isolation spectroscopic study of the free radical HCCN,
J. Chem. Phys., 1977, 66, 10, 4334, https://doi.org/10.1063/1.433724
. [all data]
Nimlos, Davico, et al., 2002, 2
Nimlos, M.R.; Davico, G.; Geise, C.M.; Wenthold, P.G.; Blanksby, W.C. Lineberger.S.J.; Hadad, C.M.; Petersson, G.A.; Ellison, G.B.,
Photoelectron spectroscopy of HCCN[sup -] and HCNC[sup -] reveals the quasilinear triplet carbenes, HCCN and HCNC,
J. Chem. Phys., 2002, 117, 9, 4323, https://doi.org/10.1063/1.1496473
. [all data]
Vogelhuber, Wren, et al., 2011
Vogelhuber, K.M.; Wren, S.W.; Shaffer, C.J.; McMahon, R.J.; McCoy, A.B.; Lineberger, W.C.,
Photoelectron spectroscopy of HC4N-,
J. Chem. Phys., 2011, 135, 20, 204307, https://doi.org/10.1063/1.3663617
. [all data]
Morter, Farhat, et al., 1993
Morter, C.L.; Farhat, S.K.; Curl, R.F.,
The ν1 fundamental of HCCN: evidence for quasilinearity,
Chem. Phys. Lett., 1993, 207, 2-3, 153, https://doi.org/10.1016/0009-2614(93)87007-P
. [all data]
Maier, Reisenauer, et al., 1998
Maier, G.; Reisenauer, H.P.; Rademacher, K.,
Cyanocarbene, Isocyanocarbene, and Azacyclopropenylidene: A Matrix-Spectroscopic Study,
Chem. Eur. J., 1998, 4, 10, 1957, https://doi.org/10.1002/(SICI)1521-3765(19981002)4:10<1957::AID-CHEM1957>3.0.CO;2-1
. [all data]
McCarthy, Gottlieb, et al., 1995
McCarthy, M.C.; Gottlieb, C.A.; Cooksy, A.L.; Thaddeus, P.,
Evidence for nonrigid HCCN,
J. Chem. Phys., 1995, 103, 18, 7779, https://doi.org/10.1063/1.470193
. [all data]
Han, Hung, et al., 1999
Han, J.-X.; Hung, P.Y.; DeSain, J.; Jones, W.E.; Curl, R.F.,
The ν1 + ν5 Band of HCCN: Determination of the ν5 Vibrational Energy,
J. Mol. Spectrosc., 1999, 198, 2, 421, https://doi.org/10.1006/jmsp.1999.7965
. [all data]
Allen, Evenson, et al., 2001
Allen, M.D.; Evenson, K.M.; Brown, J.M.,
High-Resolution Spectroscopic Measurements of the ν5 Bending Vibration--Rotation Band of HCCN in its X3Σ- State at 129 cm-1,
J. Mol. Spectrosc., 2001, 209, 2, 143, https://doi.org/10.1006/jmsp.2001.8387
. [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]
Bernheim, Kempf, et al., 1965
Bernheim, R.A.; Kempf, R.J.; Gramas, J.V.; Skell, P.S.,
Electron Paramagnetic Resonance of Triplet Alternant Methylenes. Propargylene and Homologs,
J. Chem. Phys., 1965, 43, 1, 196, https://doi.org/10.1063/1.1696454
. [all data]
Merer and Travis, 1965
Merer, A.J.; Travis, D.N.,
ABSORPTION SPECTRUM OF THE CCN RADICAL,
Can. J. Phys., 1965, 43, 10, 1795, https://doi.org/10.1139/p65-173
. [all data]
Merer and Travis, 1966
Merer, A.J.; Travis, D.N.,
THE ABSORPTION SPECTRUM OF CNC,
Can. J. Phys., 1966, 44, 2, 353, https://doi.org/10.1139/p66-029
. [all data]
Saito, Endo, et al., 1984
Saito, S.; Endo, Y.; Hirota, E.,
The microwave spectrum of a triplet carbene: HCCN in the X 3Σ- state,
J. Chem. Phys., 1984, 80, 4, 1427, https://doi.org/10.1063/1.446879
. [all data]
Brown, Saito, et al., 1990
Brown, F.X.; Saito, S.; Yamamoto, S.,
Microwave spectroscopy of isotopically substituted HCCN and its molecular structure,
J. Mol. Spectrosc., 1990, 143, 2, 203, https://doi.org/10.1016/0022-2852(91)90084-N
. [all data]
Endo and Ohshima, 1993
Endo, Y.; Ohshima, Y.,
Fourier-transform microwave spectroscopy of the HCCN radical. Determination of the hyperfine coupling constants,
J. Chem. Phys., 1993, 98, 9, 6618, https://doi.org/10.1063/1.464804
. [all data]
Sun, Kosterev, et al., 1998
Sun, F.; Kosterev, A.; Scott, G.; Litosh, V.; Curl, R.F.,
ν[sub 1] and ν[sub 1]+ν[sub 5] of DCCN: Determination of the ν[sub 5] energy and the quasilinearity of DCCN,
J. Chem. Phys., 1998, 109, 20, 8851, https://doi.org/10.1063/1.477556
. [all data]
Jones, Sun, et al., 2001
Jones, W.E.; Sun, F.; Curl, R.F.; Allen, M.D.; Evenson, K.M.; Brown, J.M.,
Can. J. Phys., 2001, 79, 389. [all data]
Hung, Sun, et al., 2001
Hung, P.Y.; Sun, F.; Hunt, N.T.; Burns, L.A.; Curl, R.F.,
High-resolution infrared spectroscopic determination of the nν[sub 5][sup ±n] vibrational energies of HCCN and DCCN,
J. Chem. Phys., 2001, 115, 20, 9331, https://doi.org/10.1063/1.1413981
. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, References
- Symbols used in this document:
EA Electron affinity ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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