Nitroethylene
- Formula: C2H3NO2
- Molecular weight: 73.0507
- IUPAC Standard InChI: InChI=1S/C2H3NO2/c1-2-3(4)5/h2H,1H2
- IUPAC Standard InChIKey: RPMXALUWKZHYOV-UHFFFAOYSA-N
- CAS Registry Number: 3638-64-0
- Chemical structure:
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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 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
C2H2NO2- + =
By formula: C2H2NO2- + H+ = C2H3NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 362.0 ± 4.6 | kcal/mol | EIAE | Shiga, Yamaoka, et al., 1972 | gas phase; From CH2=CHNO2 |
| ΔrH° | <373.60 | kcal/mol | G+TS | Bartmess, 1980 | gas phase |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 354.4 ± 5.2 | kcal/mol | H-TS | Shiga, Yamaoka, et al., 1972 | gas phase; From CH2=CHNO2 |
| ΔrG° | <366.00 | kcal/mol | IMRB | Bartmess, 1980 | gas phase |
(CAS Reg. No. 25590-58-3 • 4294967295) +
= CAS Reg. No. 25590-58-3
By formula: (CAS Reg. No. 25590-58-3 • 4294967295C2H3NO2) + C2H3NO2 = CAS Reg. No. 25590-58-3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 77.9 ± 3.0 | kcal/mol | N/A | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale |
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 as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| >1.64784 | IMRB | Bartmess, 1980 | Computations indicate HOF(A-) ca. -10, EA ca. 19 kcal/mol; B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 11.0 | EST | Takhistov and Ponomarev, 1994 | LL |
| 10.85 | PE | Pasa-Tolic, Klasine, et al., 1990 | LL |
De-protonation reactions
C2H2NO2- + =
By formula: C2H2NO2- + H+ = C2H3NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 362.0 ± 4.6 | kcal/mol | EIAE | Shiga, Yamaoka, et al., 1972 | gas phase; From CH2=CHNO2; B |
| ΔrH° | <373.60 | kcal/mol | G+TS | Bartmess, 1980 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 354.4 ± 5.2 | kcal/mol | H-TS | Shiga, Yamaoka, et al., 1972 | gas phase; From CH2=CHNO2; B |
| ΔrG° | <366.00 | kcal/mol | IMRB | Bartmess, 1980 | gas phase; B |
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.
Shiga, Yamaoka, et al., 1972
Shiga, T.; Yamaoka, H.; Arakawa, K.; Suguira, T.,
A negative ion-molecule reaction in nitroethylene,
Bull. Chem. Soc. Jpn., 1972, 45, 2065. [all data]
Bartmess, 1980
Bartmess, J.E.,
Solvent effects on ion-molecule reactions. Vinyl anions vs. conjugate addition,
J. Am. Chem. Soc., 1980, 102, 2483. [all data]
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]
Takhistov and Ponomarev, 1994
Takhistov, V.V.; Ponomarev, D.A.,
Isodesmic reactions and thermochemistry of ions,
Org. Mass Spectrom., 1994, 29, 395. [all data]
Pasa-Tolic, Klasine, et al., 1990
Pasa-Tolic, L.; Klasine, L.; McGlynn, S.P.,
The HeI PE spectrum and electronic structure of nitroethene,
Chem. Phys. Lett., 1990, 170, 113. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
EA Electron affinity ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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