1,8-Naphthalenediamine
- Formula: C10H10N2
- Molecular weight: 158.1998
- IUPAC Standard InChI: InChI=1S/C10H10N2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6H,11-12H2
- IUPAC Standard InChIKey: YFOOEYJGMMJJLS-UHFFFAOYSA-N
- CAS Registry Number: 479-27-6
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Naphthalene-1,8-diamine; 1,8-Diaminonaphthalene; 1,8-Naphthylenediamine
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Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C10H10N2+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 944.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 912.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C10H10N2+ | 6.65 ± 0.02 | ? | PE | Maier, 1974 | LLK |
De-protonation reactions
C10H9N2- + =
By formula: C10H9N2- + H+ = C10H10N2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrG° | 1441. ± 8.4 | kJ/mol | IMRE | Arnett, Venkatasubaramanian, et al., 1982 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, 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.
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Maier, 1974
Maier, J.P.,
Photoelectron spectroscopy of peri- amino naphthalenes,
Helv. Chim. Acta, 1974, 57, 994. [all data]
Arnett, Venkatasubaramanian, et al., 1982
Arnett, E.M.; Venkatasubaramanian, K.G.; McIver, R.T.; Fukuda, E.K.; Bordwell, F.G.; Press, F.D.,
Stabilization of the monoanion of 1,8-diaminonaphthalene by intramolecular hydrogen bonding. A novel case of anion homoconjugation in superbase solution,
J. Am. Chem. Soc., 1982, 104, 325. [all data]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy ΔrG° Free energy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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