Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

NOTICE: Due to scheduled maintenance at our Gaithersburg campus, this site will not be available from 5:00 pm EDT (21:00 UTC) on Friday October 25 until 5:00 pm (21:00 UTC) on Sunday October 27. We apologize for any inconvenience this outage may cause.

CH2CN anion


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

C2H2N- + Hydrogen cation = Acetonitrile

By formula: C2H2N- + H+ = C2H3N

Quantity Value Units Method Reference Comment
Deltar372.9 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar369.0 ± 4.5kcal/molCIDTGraul and Squires, 1990gas phase; B
Deltar373.3 ± 2.6kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Deltar374.8 ± 2.0kcal/molD-EAZimmerman and Brauman, 1977gas phase; B
Deltar366.6 ± 4.6kcal/molEIAEHeni and Illenberger, 1986gas phase; From MeCN; B
Quantity Value Units Method Reference Comment
Deltar365.2 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar365.6 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B
Deltar367.2 ± 2.1kcal/molH-TSZimmerman and Brauman, 1977gas phase; B

C2H2N- + Acetonitrile = (C2H2N- bullet Acetonitrile)

By formula: C2H2N- + C2H3N = (C2H2N- bullet C2H3N)

Quantity Value Units Method Reference Comment
Deltar12.8 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Deltar15.70kcal/molTDAsHiraoka, Mizure, et al., 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar22.8cal/mol*KPHPMSHiraoka, Mizure, et al., 1988gas phase; M
Deltar13.4cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar8.8 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B
Deltar8.90kcal/molTDAsHiraoka, Mizure, et al., 1988gas phase; B

C2H2N- + Water = (C2H2N- bullet Water)

By formula: C2H2N- + H2O = (C2H2N- bullet H2O)

Quantity Value Units Method Reference Comment
Deltar13.2 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar17.6cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar7.9 ± 1.0kcal/molTDAsMeot-ner, 1988gas 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

C2H2N- + Hydrogen cation = Acetonitrile

By formula: C2H2N- + H+ = C2H3N

Quantity Value Units Method Reference Comment
Deltar372.9 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar369.0 ± 4.5kcal/molCIDTGraul and Squires, 1990gas phase
Deltar373.3 ± 2.6kcal/molG+TSCumming and Kebarle, 1978gas phase
Deltar374.8 ± 2.0kcal/molD-EAZimmerman and Brauman, 1977gas phase
Deltar366.6 ± 4.6kcal/molEIAEHeni and Illenberger, 1986gas phase; From MeCN
Quantity Value Units Method Reference Comment
Deltar365.2 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar365.6 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase
Deltar367.2 ± 2.1kcal/molH-TSZimmerman and Brauman, 1977gas 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

C2H2N- + Acetonitrile = (C2H2N- bullet Acetonitrile)

By formula: C2H2N- + C2H3N = (C2H2N- bullet C2H3N)

Quantity Value Units Method Reference Comment
Deltar12.8 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Deltar15.70kcal/molTDAsHiraoka, Mizure, et al., 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar22.8cal/mol*KPHPMSHiraoka, Mizure, et al., 1988gas phase; M
Deltar13.4cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar8.8 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B
Deltar8.90kcal/molTDAsHiraoka, Mizure, et al., 1988gas phase; B

C2H2N- + Water = (C2H2N- bullet Water)

By formula: C2H2N- + H2O = (C2H2N- bullet H2O)

Quantity Value Units Method Reference Comment
Deltar13.2 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar17.6cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar7.9 ± 1.0kcal/molTDAsMeot-ner, 1988gas 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   «lambda»min 
 (nm) 
 «lambda»max 
 (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

oEnergy 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