2-Naphthalenamine
- Formula: C10H9N
- Molecular weight: 143.1852
- 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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Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 579.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 383. ± 3. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 73.9 | kJ/mol | A | Stephenson and Malanowski, 1987 | Based on data from 283. to 323. K.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
63.5 | 403. | A | Stephenson and Malanowski, 1987 | Based on data from 388. to 579. K. See also Stull, 1947.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
74.06 ± 0.84 | 283. | V | Karyakin, Rabinovich, et al., 1968 | ALS |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
23.33 | 386.2 | Acree, 1991 | AC |
Gas phase ion energetics data
Go To: Top, Phase change 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, Phase change 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.
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Karyakin, Rabinovich, et al., 1968
Karyakin, N.V.; Rabinovich, I.B.; Pakhomov, L.G.,
Heats of sublimation of naphthalene and its monosubstituted β-derivatives,
Russ. J. Phys. Chem. (Engl. Transl.), 1968, 42, 954. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [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, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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