pyrrolide anion
- Formula: C4H4N-
- Molecular weight: 66.0818
- IUPAC Standard InChI: InChI=1S/C4H4N/c1-2-4-5-3-1/h1-4H/q-1
- IUPAC Standard InChIKey: KFFMWJLUQMFKOH-UHFFFAOYSA-N
- CAS Registry Number: 23303-09-5
- Chemical structure:
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Reaction thermochemistry data
Go To: Top, 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: C4H4N- + H+ = C4H5N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1504.3 ± 1.0 | kJ/mol | D-EA | Gianola, Ichino, et al., 2004 | gas phase; B |
| ΔrH° | 1500. ± 9.2 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrH° | 1505. ± 12. | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
| ΔrH° | 1500. ± 21. | kJ/mol | EIAE | Muftakhov, Vasil'ev, et al., 1999 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1468. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrG° | 1472. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
+
= (
•
)
By formula: C4H4N- + H2O = (C4H4N- • H2O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 65.7 ± 4.2 | kJ/mol | TDAs | Meot-ner, 1988 | gas phase; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 96.7 | J/mol*K | PHPMS | Meot-ner, 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 37. ± 4.2 | kJ/mol | TDAs | Meot-ner, 1988 | gas phase; B |
+
= (
•
)
By formula: C4H4N- + C4H5N = (C4H4N- • C4H5N)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 111. ± 4.2 | kJ/mol | TDAs | Meot-ner, 1988 | gas phase; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 147. | J/mol*K | PHPMS | Meot-ner, 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 68.2 ± 4.2 | kJ/mol | TDAs | Meot-ner, 1988 | gas phase; B |
+
= (
•
)
By formula: C4H4N- + CH4O = (C4H4N- • CH4O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 77.8 ± 4.2 | kJ/mol | TDAs | Meot-ner, 1988 | gas phase; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 115. | J/mol*K | PHPMS | Meot-ner, 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 43.5 ± 4.2 | kJ/mol | TDAs | Meot-ner, 1988 | gas phase; B |
+
= (
•
)
By formula: C4H4N- + C3H6O = (C4H4N- • C3H6O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 54.8 ± 4.2 | kJ/mol | TDAs | Meot-ner, 1988 | gas phase; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 85.8 | J/mol*K | PHPMS | Meot-ner, 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 29. ± 4.2 | kJ/mol | TDAs | Meot-ner, 1988 | gas phase; B |
+
= (
•
)
By formula: C4H4N- + C2H3N = (C4H4N- • C2H3N)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 66.1 ± 4.2 | kJ/mol | TDAs | Meot-ner, 1988 | gas phase; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 97.9 | J/mol*K | PHPMS | Meot-ner, 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 37. ± 4.2 | kJ/mol | TDAs | Meot-ner, 1988 | gas phase; B |
+
= (
•
)
By formula: C4H4N- + C3H7NO = (C4H4N- • C3H7NO)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 110. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 130. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
Free energy of reaction
| ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 49.8 | 497. | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
( •
) +
= (
• 2
)
By formula: (C4H4N- • H2O) + H2O = (C4H4N- • 2H2O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 50.6 | kJ/mol | PHPMS | Meot-ner, 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 97.1 | J/mol*K | PHPMS | Meot-ner, 1988 | gas phase; M |
( •
) +
= (
• 2
)
By formula: (C4H4N- • C4H5N) + C4H5N = (C4H4N- • 2C4H5N)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 71.5 | kJ/mol | PHPMS | Meot-ner, 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 131. | J/mol*K | PHPMS | Meot-ner, 1988 | gas phase; M |
( •
) +
= (
• 2
)
By formula: (C4H4N- • C3H6O) + C3H6O = (C4H4N- • 2C3H6O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 44.8 | kJ/mol | PHPMS | Meot-ner, 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 79.5 | J/mol*K | PHPMS | Meot-ner, 1988 | gas phase; M |
+
= (
•
)
By formula: C4H4N- + C2H5NO = (C4H4N- • C2H5NO)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 110. ± 8. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 130. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1988 | gas phase; M |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Gianola, Ichino, et al., 2004
Gianola, A.J.; Ichino, T.; Hoenigman, R.L.; Kato, S.; Bierbaum, V.M.; Lineberger, W.C.,
Thermochemistry and electronic structure of the pyrrolyl radical,
J. Phys. Chem. A, 2004, 108, 46, 10326-10335, https://doi.org/10.1021/jp047790+
. [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]
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]
Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Khatymov, R.V.; Mazunov, V.A.; Takhistov, V.V.; Travkin, O.V.; Yakovleva, E.V.,
Thermochemistry of negatively charged ions. II. Energetics of formation of negative ions from acridanone and some of its derivatives,
Rapid Commun. Mass Spectrom., 1999, 13, 10, 912-923, https://doi.org/10.1002/(SICI)1097-0231(19990530)13:10<912::AID-RCM585>3.0.CO;2-W
. [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]
Meot-Ner (Mautner), 1988
Meot-Ner (Mautner), M.,
Models for Strong Interactions in Proteins and Enzymes. 2. Interactions of Ions with the Peptide Link and Imidazole,
J. Am. Chem. Soc., 1988, 110, 10, 3075, https://doi.org/10.1021/ja00218a014
. [all data]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature 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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