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, 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
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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, 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 |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, 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]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, 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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