2-Naphthalenamine, N-phenyl-
- Formula: C16H13N
- Molecular weight: 219.2811
- IUPAC Standard InChI: InChI=1S/C16H13N/c1-2-8-15(9-3-1)17-16-11-10-13-6-4-5-7-14(13)12-16/h1-12,17H
- IUPAC Standard InChIKey: KEQFTVQCIQJIQW-UHFFFAOYSA-N
- CAS Registry Number: 135-88-6
- 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: 2-Naphthylamine, N-phenyl-; β-Naphthylphenylamine; Aceto PBN; AgeRite Powder; Antioxidant PBN; Antioxidant 116; N-(2-Naphthyl)aniline; N-Phenyl-β-naphthylamine; N-Phenyl-2-naphthylamine; Neosone D; Neozon D; Neozone; Neozone D; Nilox PBNA; Nonox D; Nonox DN; PBNA; Stabilizator AR; Vulkanox PBN; 2-Anilinonaphthalene; 2-Naphthylphenylamine; 2-Phenylaminonaphthalene; Anilinonaphthalene; NCI-C02915; Phenyl-β-naphthylamine; Phenyl-2-naphthylamine; N-Fenyl-2-aminonaftalen; Fenyl-β-naftylamin; N-Phenyl-2-naphthalenamine; N-(2-Naphthyl)-N-phenylamine; Stabilizer AR; Antioxidant D; Nocrac D; Naftam 2; N-β-Naphthyl-N-phenylamine; Stabilator AR; AK 1; AK 1 (stabilizer); NSC 37151; Noclizer D
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Condensed phase thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | 38.8 ± 0.41 | kcal/mol | Ccb | Medard and Thomas, 1954 | Heat of combustion corrected for pressure |
| ΔfH°solid | 41.67 | kcal/mol | Ccb | Medard, 1954 | Heat of combustion corrected for pressure |
| ΔfH°solid | 58.7 | kcal/mol | Ccb | Lemoult, 1906 | Author value for hf298-condensed=50.3 kcal/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1987.66 ± 0.41 | kcal/mol | Ccb | Medard and Thomas, 1954 | Heat of combustion corrected for pressure |
| ΔcH°solid | -1990.55 | kcal/mol | Ccb | Medard, 1954 | Heat of combustion corrected for pressure |
| ΔcH°solid | -1987.07 ± 0.43 | kcal/mol | Ccb | Roberts and Jessup, 1948 | |
| ΔcH°solid | -2007.6 | kcal/mol | Ccb | Lemoult, 1906 | Author value for hf298-condensed=50.3 kcal/mol |
Phase change data
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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
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 668.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 21.2 | 398. | A | Stephenson and Malanowski, 1987 | Based on data from 383. to 520. K.; AC |
Enthalpy of sublimation
| ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 27.68 | 348. | GS | Stephenson and Malanowski, 1987 | Based on data from 333. to 363. K. See also Fel'dshtein and Kuz'minskii, 1971.; AC |
Gas phase ion energetics data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
| IE (eV) | Method | Reference |
|---|---|---|
| 7.15 | CTS | Kinoshita, 1962 |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- SOLID (SPLIT MULL), FLUOROLUBE FOR 3800-1330 CM-1, NUJOL FOR 1330-460 CM-1; DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
- SOLUTION (10% CS2 FOR 3800-460 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
Mass spectrum (electron ionization)
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
| Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | Japan AIST/NIMC Database- Spectrum MS-NW-1721 |
| NIST MS number | 229398 |
UV/Visible spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
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| Source | Fihtengolts, et al., 1969 |
|---|---|
| Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
| Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
| Source reference | RAS UV No. 20150 |
| Instrument | SF-4 |
| Melting point | 108 |
Gas Chromatography
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | 5 % Phenyl methyl siloxane | 2222. | Yasuhara, Shiraishi, et al., 1997 | 25. m/0.31 mm/0.52 μm, He; Program: 50C(2min) => (20C/min) => 120C => (7C/min) => 310C(10min) |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Ultra-1 | 2169. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Subscription Links, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Medard and Thomas, 1954
Medard, L.; Thomas, M.,
Chaleurs de combustion de vingt-quatre substances explosives ou apparentees a des explosifs,
Mem. Poudres, 1954, 36, 97-127. [all data]
Medard, 1954
Medard, L.,
Tables thermochimiques a l'usage des techniciens des substances explosives,
Mem. Artillerie Fr. Sci. Tech. Armement, 1954, 28, 415-492. [all data]
Lemoult, 1906
Lemoult, M.P.,
Thermochimie. - Chaleur de combustion et de formation de quelques composes cycliques azotes,
Compt. Rend., 1906, 143, 772-775. [all data]
Roberts and Jessup, 1948
Roberts, D.E.; Jessup, R.S.,
Heat of combustion of phenyl-beta-naphthylamine (N-phenyl-2-naphthylamine),
J. Res. NBS, 1948, 40, 281-283. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 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]
Fel'dshtein and Kuz'minskii, 1971
Fel'dshtein, L.S.; Kuz'minskii, A.S.,
Kauch. Rezina, 1971, 30, 11, 15. [all data]
Kinoshita, 1962
Kinoshita, M.,
The absorption spectra of the molecular complexes of aromatic compounds with p-bromanil,
Bull. Chem. Soc. Japan, 1962, 35, 1609. [all data]
Fihtengolts, et al., 1969
Fihtengolts, V.S., et al.,
Atlas of UV Absorption Spectra of Substances Used in Synthetic Rubber Manufacture, 1969, 66. [all data]
Yasuhara, Shiraishi, et al., 1997
Yasuhara, A.; Shiraishi, H.; Nishikawa, M.; Yamamoto, T.; Uehiro, T.; Nakasugi, O.; Okumura, T.; Kenmotsu, K.; Fukui, H.; Nagase, M.; Ono, Y.; Kawagoshi, Y.; Baba, K.; Noma, Y.,
Determination of organic components in leachates from hazardous waste disposal sites in Japan by gas chromatography-mass spectrometry,
J. Chromatogr. A, 1997, 774, 1-2, 321-332, https://doi.org/10.1016/S0021-9673(97)00078-2
. [all data]
Okumura, 1991
Okumura, T.,
retention indices of environmental chemicals on methyl silicone capillary column,
Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333
. [all data]
Notes
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- Symbols used in this document:
Tboil Boiling point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔsubH Enthalpy of sublimation ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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