Naphthalene, 1-nitro-
- Formula: C10H7NO2
- Molecular weight: 173.1681
- IUPAC Standard InChIKey: RJKGJBPXVHTNJL-UHFFFAOYSA-N
- CAS Registry Number: 86-57-7
- Chemical structure:
This structure is also available as a 2d Mol file - Species with the same structure:
- Other names: α-Nitronaphthalene; Nitrol; Nitrol (pesticide); 1-Nitronaphthalene; NCI-C01956; 1-Nitronaftalen
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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 | 10.93 | kcal/mol | Ccb | Rinkenbach, 1930 | Author hf298_condensed[kcal/mol]=7.147 |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1189.89 | kcal/mol | Ccb | Badoche, 1937 | |
ΔcH°solid | -1190.55 | kcal/mol | Ccb | Rinkenbach, 1930 | Author hf298_condensed[kcal/mol]=7.147 |
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
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 | 577.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 327.7 | K | N/A | Rampolla and Smyth, 1958 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 329.39 | K | N/A | Campetti, 1914 | Uncertainty assigned by TRC = 3. K; isomer not identified; TRC |
Tfus | 330. | K | N/A | Battelli, 1884 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 22.7 ± 0.1 | kcal/mol | ME | Ribeiro da Silva, Amaral, et al., 2006 | Based on data from 305. to 321. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
15.9 | 347. | A | Stephenson and Malanowski, 1987 | Based on data from 332. to 580. K.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
22.6 ± 0.1 | 313. | ME | Ribeiro da Silva, Amaral, et al., 2006 | Based on data from 305. to 321. K.; AC |
25.55 | 328.5 | N/A | Stephenson and Malanowski, 1987 | Based on data from 325. to 332. K.; AC |
16.38 ± 0.45 | 283. | C | Radchenko and Kitaigorodskii, 1974 | ALS |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
4.13 | 328.9 | DSC | Kestens, Auclair, et al., 2010 | AC |
4.405 | 329.9 | N/A | Acree, 1991 | AC |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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:
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
B - John E. Bartmess
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
1.23 ± 0.10 | TDEq | Heinis, Chowdhury, et al., 1993 | ΔGea(423 K)= -27.9 kcal/mol ΔSea=-0.9; B |
<1.240 ± 0.050 | PD | Mock and Grimsrud, 1989 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.59 | PE | Klasinc, Kovac, et al., 1983 | LBLHLM |
8.60 ± 0.01 | PI | Kotov and Potapov, 1972 | LLK |
IR Spectrum
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compiled by: Coblentz Society, Inc.
- SOLUTION (10% CCl4 FOR 3800-1330, 10% CS2 FOR 1330-450 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm-1 resolution
- SOLUTION (2% CCl4 FOR 3800-1330, 2% CS2 FOR 1330-450 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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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 | Chemical Concepts |
NIST MS number | 156440 |
Gas Chromatography
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References, Notes
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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | DB-5 | 140. | 1615.66 | Hobbs and Conde, 1992 | 30. m/0.25 mm/0.25 μm |
Capillary | DB-5 | 140. | 1615.84 | Hobbs and Conde, 1992 | 30. m/0.25 mm/0.25 μm |
Capillary | SE-30 | 180. | 1597. | Korhonen and Lind, 1985 | N2; Column length: 25. m; Column diameter: 0.33 mm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1610.84 | Hobbs and Conde, 1992 | 30. m/0.25 mm/0.25 μm, 5. K/min; Tstart: 40. C; Tend: 300. C |
Capillary | DB-5 | 1612.87 | Hobbs and Conde, 1992 | 30. m/0.25 mm/0.25 μm, 5. K/min; Tstart: 40. C; Tend: 300. C |
Capillary | SE-30 | 1586. | Korhonen and Lind, 1985 | N2, 10. K/min; Column length: 25. m; Column diameter: 0.33 mm; Tstart: 100. C; Tend: 320. C |
Capillary | SE-30 | 1589. | Korhonen and Lind, 1985 | N2, 6. K/min; Column length: 25. m; Column diameter: 0.33 mm; Tstart: 140. C; Tend: 320. C |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | SE-30 | 200. | 1618. | Korhonen and Lind, 1985 | N2; Column length: 25. m; Column diameter: 0.33 mm |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Squalane | 1597. | Chen, 2008 | Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-52 | 274.40 | White, Robbat, et al., 1983 | 30. m/0.3 mm/0.25 μm, He, 4. K/min; Tstart: 25. C; Tend: 295. C |
Capillary | SE-52 | 274.18 | White, Robbat, et al., 1983 | 30. m/0.2 mm/0.25 μm, He, 4. K/min; Tstart: 25. C; Tend: 295. C |
Capillary | SE-52 | 266.70 | White, Robbat, et al., 1983 | 30. m/0.3 mm/0.25 μm, He, 4. K/min; Tstart: 100. C; Tend: 300. C |
Capillary | SE-52 | 274.07 | White, Robbat, et al., 1983 | 30. m/0.3 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 300. C |
Capillary | SE-52 | 272.40 | White, Robbat, et al., 1983 | 30. m/0.3 mm/0.25 μm, He, 4. K/min; Tstart: 70. C; Tend: 300. C |
Capillary | SE-52 | 274.95 | Vassilaros, Kong, et al., 1982 | 20. m/0.30 mm/0.25 μm, H2, 40. C @ 2. min, 4. K/min; Tend: 265. C |
Lee's RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 273.0 | Tucminen, Wickstrom, et al., 1986 | Program: not specified |
Capillary | OV-101 | 274.0 | Tucminen, Wickstrom, et al., 1986 | Program: not specified |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Rinkenbach, 1930
Rinkenbach, W.H.,
The heats of combustion and formation of aromatic nitro compounds,
J. Am. Chem. Soc., 1930, 52, 115-120. [all data]
Badoche, 1937
Badoche, M.,
Determinations de la chaleur de combustion de quelques derives nitres du naphtalene,
Bull. Soc. Chim. France, 1937, 4, 549-557. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Rampolla and Smyth, 1958
Rampolla, R.W.; Smyth, C.P.,
J. Am. Chem. Soc., 1958, 80, 1057. [all data]
Campetti, 1914
Campetti, A.,
Specific heats of some binary liquid mixtures.,
Atti R. Accad. Naz. Lincei, Mem. Cl. Sci. Fis. Mat. Nat., 1914, 48, 968-77. [all data]
Battelli, 1884
Battelli, A.,
Atti del Reale Istituto Veneto di Scienze Lettere ed Arti, 1884, 3, 1781. [all data]
Ribeiro da Silva, Amaral, et al., 2006
Ribeiro da Silva, Manuel A.V.; Amaral, Luísa M.P.F.; Santos, Ana Filipa L.O.M.; Gomes, José R.B.,
Thermochemistry of nitronaphthalenes and nitroanthracenes,
The Journal of Chemical Thermodynamics, 2006, 38, 6, 748-755, https://doi.org/10.1016/j.jct.2005.08.007
. [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]
Radchenko and Kitaigorodskii, 1974
Radchenko, L.G.; Kitaigorodskii, A.I.,
The vapour pressures and heats of sublimation of naphthalene, biphenyl, octafluoronaphthalene, decafluorobiphenyl, acenaphthene and α-nitronaphthalene,
Russ. J. Phys. Chem. (Engl. Transl.), 1974, 48, 1595. [all data]
Kestens, Auclair, et al., 2010
Kestens, Vikram; Auclair, Guy; Drozdzewska, Katarzyna; Held, Andrea; Roebben, Gert; Linsinger, Thomas,
Thermodynamic property values of selected polycyclic aromatic hydrocarbons measured by differential scanning calorimetry,
J Therm Anal Calorim, 2010, 99, 1, 245-261, https://doi.org/10.1007/s10973-009-0440-6
. [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]
Heinis, Chowdhury, et al., 1993
Heinis, T.; Chowdhury, S.; Kebarle, P.,
Electron Affinities of Naphthalene, Anthracene and Substituted Naphthalenes and Anthracenes,
Org. Mass Spectrom., 1993, 28, 4, 358, https://doi.org/10.1002/oms.1210280416
. [all data]
Mock and Grimsrud, 1989
Mock, R.S.; Grimsrud, E.P.,
Gas-Phase Electron Photodetachment Spectroscopy of the Molecular Anions of Nitroaromatic Hydrocarbons at Atmospheric Pressure,
J. Am. Chem. Soc., 1989, 111, 8, 2861, https://doi.org/10.1021/ja00190a020
. [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]
Kotov and Potapov, 1972
Kotov, B.V.; Potapov, V.K.,
Ionization potentials of strong organic electron acceptors,
Khim. Vys. Energ., 1972, 6, 375. [all data]
Hobbs and Conde, 1992
Hobbs, J.R.; Conde, E.P.,
Gas chromatographic retention indices of explosives and nitro-compounds
in Advances in Analysis and Detection of Explosives: Proceedings of the 4th International Symposium on Analysis of Detection of Explosives, September 7-10, 1992, Jerusalem Israel, J. Yinon, ed(s)., Kluwer Academic Publishers, Netherlands, 1992, 153-164. [all data]
Korhonen and Lind, 1985
Korhonen, I.O.O.; Lind, M.A.,
Gas-liquid chromatographic analyses. XXXIV. Separation and retention indices with retention increments of some nitrated polynuclear aromatic hydrocarbons on a low-polarity (SE-30) capillary column,
J. Chromatogr., 1985, 322, 71-81, https://doi.org/10.1016/S0021-9673(01)97660-5
. [all data]
Chen, 2008
Chen, H.-F.,
Quantitative prediction of gas chromatography retention indices with support vector machines, radial basis neutral networks and multiple linear regression,
Anal. Chim. Acta, 2008, 609, 1, 24-36, https://doi.org/10.1016/j.aca.2008.01.003
. [all data]
White, Robbat, et al., 1983
White, C.M.; Robbat, A., Jr.; Hoes, R.M.,
Gas chromatographic retention characteristics of nitrated polycyclic aromatic hydrocarbons on SE-52,
Chromatographia, 1983, 17, 11, 605-612, https://doi.org/10.1007/BF02261944
. [all data]
Vassilaros, Kong, et al., 1982
Vassilaros, D.L.; Kong, R.C.; Later, D.W.; Lee, M.L.,
Linear retention index system for polycyclic aromatic compounds. Critical evaluation and additional indices,
J. Chromatogr., 1982, 252, 1-20, https://doi.org/10.1016/S0021-9673(01)88394-1
. [all data]
Tucminen, Wickstrom, et al., 1986
Tucminen, A.; Wickstrom, K.; Pyysalo, H.,
Determination of Polycyclic Aromatic Compounds by GLC-Selected Ion Monitoring (SIM) Technique,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 8, 469-471, https://doi.org/10.1002/jhrc.1240090813
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
EA Electron affinity Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions 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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