2-Naphthalenamine
- Formula: C10H9N
- Molecular weight: 143.1852
- IUPAC Standard InChI: InChI=1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2
- IUPAC Standard InChIKey: JBIJLHTVPXGSAM-UHFFFAOYSA-N
- CAS Registry Number: 91-59-8
- 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: 2-Naphthylamine; β-Naphthylamine; C.I. 37270; Fast Scarlet Base B; 2-Aminonaphthalene; 2-Aminonaftalen; β-naftyloamina; β-Naftalamin; β-Naftilamina; 2-Naftylamin; 2-Naftylamine; 2-Naphthalamine; β-Naftylamin; β-Naphthylamin; 2-Naphthylamin; 6-Naphthylamine; RCRA waste number U168; UN 1650; USAF CB-22
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Condensed phase 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | 79.9 | kJ/mol | Ccb | Pushin, 1954 | Author's hf298_condensed=16.6 kcal/mol; ALS |
| ΔfH°solid | 77.8 | kJ/mol | Ccb | Schmidt and Becker, 1933 | ALS |
| ΔfH°solid | 81.6 | kJ/mol | Ccb | Lemoult, 1907 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -5301. | kJ/mol | Ccb | Pushin, 1954 | Author's hf298_condensed=16.6 kcal/mol; ALS |
| ΔcH°solid | -5279.0 ± 4.6 | kJ/mol | Ccb | Willis, 1947 | Reanalyzed by Cox and Pilcher, 1970, Original value = -5273.5 ± 4.6 kJ/mol; ALS |
| ΔcH°solid | -5304.1 | kJ/mol | Ccb | Schmidt and Becker, 1933 | ALS |
| ΔcH°solid | -5284.0 ± 5.4 | kJ/mol | Ccb | Milone and Rossignoli, 1932 | Reanalyzed by Cox and Pilcher, 1970, Original value = -5309.75 kJ/mol; ALS |
| ΔcH°solid | -5303.2 | kJ/mol | Ccb | Lemoult, 1907 | ALS |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 125.9 | 293. | Campbell and Campbell, 1940 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase 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 evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C10H9N+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 7.1 ± 0.1 | eV | N/A | N/A | L |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 7.03 | PE | Klasinc, Kovac, et al., 1983 | LBLHLM |
| 7.10 ± 0.02 | PE | Maier, 1974 | LLK |
| 7.4 ± 0.1 | CTS | Farrell and Newton, 1966 | RDSH |
| 7.2 | PI | Terenin, 1961 | RDSH |
| 7.5 | CTS | Briegleb and Czekalla, 1959 | RDSH |
| 7.55 | PE | Klasinc, Kovac, et al., 1983 | Vertical value; LBLHLM |
| 7.56 | PE | Utsunomiya, Kobayashi, et al., 1975 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C9H7+ | 14.28 | HCN+H | EI | Occolowitz and White, 1968 | RDSH |
| C9H8+ | 12.59 | HCN | EI | Occolowitz and White, 1968 | RDSH |
References
Go To: Top, Condensed phase 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.
Pushin, 1954
Pushin, N.A.,
Heats of combustion and heats of formation of isomeric organic compounds,
Bull. Soc. Chim. Belgrade, 1954, 19, 531-547. [all data]
Schmidt and Becker, 1933
Schmidt, V.A.; Becker, F.,
Die Bildungswarme von Nitrocellulofen, Nitroglycerin und anderen widuigen Beltandteilen von Treibmitteln,
Z. Gesamte Schiess Sprengstoffwes., 1933, 33, 280-282. [all data]
Lemoult, 1907
Lemoult, M.P.,
Recherches theoriques et experimentales sur les chaleurs de combustion et de formation des composes organiques,
Ann. Chim. Phys., 1907, 12, 395-432. [all data]
Willis, 1947
Willis, J.B.,
The heats of combustion of some organic bases and their salts. The resonance energies of acridine and phenazine,
Trans. Faraday Soc., 1947, 43, 97-102. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Milone and Rossignoli, 1932
Milone, M.; Rossignoli, P.,
Sul calore di combustione di alcune miscele di composti organici,
Gazz. Chim. Ital., 1932, 62, 644-655. [all data]
Campbell and Campbell, 1940
Campbell, A.N.; Campbell, A.J.R.,
The heats of solution, heats of formation,
specific heats and equilibrium diagrams of certain molecular compounds. J. Am. Chem. Soc., 1940, 62, 291-297. [all data]
Klasinc, Kovac, et al., 1983
Klasinc, L.; Kovac, B.; Gusten, H.,
Photoelectron spectra of acenes. Electronic structure and substituent effects,
Pure Appl. Chem., 1983, 55, 289. [all data]
Maier, 1974
Maier, J.P.,
Photoelectron spectroscopy of peri- amino naphthalenes,
Helv. Chim. Acta, 1974, 57, 994. [all data]
Farrell and Newton, 1966
Farrell, P.G.; Newton, J.,
Ionization potentials of primary aromatic amines and aza-hydrocarbons,
Tetrahedron Lett., 1966, 5517. [all data]
Terenin, 1961
Terenin, A.,
Charge transfer in organic solids, induced by light,
Proc. Chem. Soc., London, 1961, 321. [all data]
Briegleb and Czekalla, 1959
Briegleb, G.; Czekalla, J.,
Die Bestimmung von lonisierungsenergien aus den Spektren von Elektronenubergangskomplexen,
Z.Elektrochem., 1959, 63, 6. [all data]
Utsunomiya, Kobayashi, et al., 1975
Utsunomiya, C.; Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of substituted naphthalenes,
Bull. Chem. Soc. Jpn., 1975, 48, 1852. [all data]
Occolowitz and White, 1968
Occolowitz, J.L.; White, G.L.,
Energetic considerations in the assignment of some fragment ion structures,
Australian J. Chem., 1968, 21, 997. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,solid Constant pressure heat capacity of solid IE (evaluated) Recommended ionization energy ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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