CH2CN anion
- Formula: C2H2N-
- Molecular weight: 40.0445
- CAS Registry Number: 21438-99-3
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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, Ion clustering 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
By formula: C2H2N- + H+ = C2H3N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 372.9 ± 2.1 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 369.0 ± 4.5 | kcal/mol | CIDT | Graul and Squires, 1990 | gas phase; B |
ΔrH° | 373.3 ± 2.6 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
ΔrH° | 374.8 ± 2.0 | kcal/mol | D-EA | Zimmerman and Brauman, 1977 | gas phase; B |
ΔrH° | 366.6 ± 4.6 | kcal/mol | EIAE | Heni and Illenberger, 1986 | gas phase; From MeCN; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 365.2 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 365.6 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
ΔrG° | 367.2 ± 2.1 | kcal/mol | H-TS | Zimmerman and Brauman, 1977 | gas phase; B |
By formula: C2H2N- + C2H3N = (C2H2N- • C2H3N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 12.8 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase; B,M |
ΔrH° | 15.70 | kcal/mol | TDAs | Hiraoka, Mizure, et al., 1988 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 22.8 | cal/mol*K | PHPMS | Hiraoka, Mizure, et al., 1988 | gas phase; M |
ΔrS° | 13.4 | cal/mol*K | PHPMS | Meot-ner, 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 8.8 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase; B |
ΔrG° | 8.90 | kcal/mol | TDAs | Hiraoka, Mizure, et al., 1988 | gas phase; B |
By formula: C2H2N- + H2O = (C2H2N- • H2O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 13.2 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 17.6 | cal/mol*K | PHPMS | Meot-ner, 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 7.9 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase; B |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, Ion clustering 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
Protonation reactions
By formula: C2H2N- + H+ = C2H3N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 372.9 ± 2.1 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale |
ΔrH° | 369.0 ± 4.5 | kcal/mol | CIDT | Graul and Squires, 1990 | gas phase |
ΔrH° | 373.3 ± 2.6 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase |
ΔrH° | 374.8 ± 2.0 | kcal/mol | D-EA | Zimmerman and Brauman, 1977 | gas phase |
ΔrH° | 366.6 ± 4.6 | kcal/mol | EIAE | Heni and Illenberger, 1986 | gas phase; From MeCN |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 365.2 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale |
ΔrG° | 365.6 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase |
ΔrG° | 367.2 ± 2.1 | kcal/mol | H-TS | Zimmerman and Brauman, 1977 | gas phase |
Ion clustering data
Go To: Top, Reaction thermochemistry data, 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: C2H2N- + C2H3N = (C2H2N- • C2H3N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 12.8 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase; B,M |
ΔrH° | 15.70 | kcal/mol | TDAs | Hiraoka, Mizure, et al., 1988 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 22.8 | cal/mol*K | PHPMS | Hiraoka, Mizure, et al., 1988 | gas phase; M |
ΔrS° | 13.4 | cal/mol*K | PHPMS | Meot-ner, 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 8.8 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase; B |
ΔrG° | 8.90 | kcal/mol | TDAs | Hiraoka, Mizure, et al., 1988 | gas phase; B |
By formula: C2H2N- + H2O = (C2H2N- • H2O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 13.2 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 17.6 | cal/mol*K | PHPMS | Meot-ner, 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 7.9 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase; B |
Vibrational and/or electronic energy levels
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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: Dip
Energy (cm-1) |
Med. | Transition | λmin (nm) |
λmax (nm) |
References | ||
---|---|---|---|---|---|---|---|
To = 12428.665 ± 0.002 | gas | Lykke, Neumark, et al., 1987 | |||||
Wetzel and Brauman, 1989 | |||||||
Vib. sym. |
No. | Approximate type of mode |
cm-1 | Med. | Method | References | |
---|---|---|---|---|---|---|---|
951 ± 10 | gas | PD | Wetzel and Brauman, 1989 | ||||
b1 | 5 | H2CC deform. | 692 ± 10 | gas | PD | Wetzel and Brauman, 1989 | |
State: X
Vib. sym. |
No. | Approximate type of mode |
cm-1 | Med. | Method | References | |
---|---|---|---|---|---|---|---|
a' | 5 | H2CC deform. | 424.77 | gas | PD PE | Marks, Wetzel, et al., 1986 Moran, Ellis, et al., 1987 Lykke, Neumark, et al., 1987 | |
Additional references: Jacox, 1994, page 252
Notes
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, Ion clustering 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.
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]
Graul and Squires, 1990
Graul, S.T.; Squires, R.R.,
Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions,
J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007
. [all data]
Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P.,
Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A),
Can. J. Chem., 1978, 56, 1. [all data]
Zimmerman and Brauman, 1977
Zimmerman, A.H.; Brauman, J.I.,
Electron photodetachment from negative ions of C2v symmetry. Electron affinities of allyl and cyanomethyl radicals,
J. Am. Chem. Soc., 1977, 99, 3565. [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]
Meot-ner, 1988
Meot-ner, M.,
The Ionic Hydrogen Bond and Solvation. 7. Interaction Energies of Carbanions with Solvent Molecules,
J. Am. Chem. Soc., 1988, 110, 12, 3858, https://doi.org/10.1021/ja00220a022
. [all data]
Hiraoka, Mizure, et al., 1988
Hiraoka, K.; Mizure, S.; Yamabe, S.; Nakatsuji, Y.,
Gas Phase Clustering Reactions of CN- and CH2CN- with MeCN,
Chem. Phys. Lett., 1988, 148, 6, 497, https://doi.org/10.1016/0009-2614(88)80320-8
. [all data]
Lykke, Neumark, et al., 1987
Lykke, K.R.; Neumark, D.M.; Andersen, T.; Trapa, V.J.; Lineberger, W.C.,
Autodetachment spectroscopy and dynamics of CH2CN- and CD2CN-,
J. Chem. Phys., 1987, 87, 12, 6842, https://doi.org/10.1063/1.453379
. [all data]
Wetzel and Brauman, 1989
Wetzel, D.M.; Brauman, J.I.,
Rotational structure in an excited vibronic band of the dipole-supported state of cyanomethyl anion, CH2CN-,
J. Chem. Phys., 1989, 90, 1, 68, https://doi.org/10.1063/1.456468
. [all data]
Marks, Wetzel, et al., 1986
Marks, J.; Wetzel, D.M.; Comita, P.B.; Brauman, J.I.,
A dipole supported state in cyanomethyl anion, the conjugate base of acetonitrile. Rotational band assignments in the electron photodetachment spectrum of -CH2CN,
J. Chem. Phys., 1986, 84, 5284. [all data]
Moran, Ellis, et al., 1987
Moran, S.; Ellis, H.B., Jr.; DeFrees, D.J.; McLean, A.D.; Ellison, G.B.,
Carbanion spectroscopy: CH2CN-,
J. Am. Chem. Soc., 1987, 109, 5996. [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]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Vibrational and/or electronic energy levels, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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