Naphthalene, 1-methyl-
- Formula: C11H10
- Molecular weight: 142.1971
- IUPAC Standard InChIKey: QPUYECUOLPXSFR-UHFFFAOYSA-N
- CAS Registry Number: 90-12-0
- 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: α-Methylnaphthalene; 1-Methylnaphthalene; Methyl-1-naphthalene
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Gas 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 116.9 ± 2.7 | kJ/mol | Ccb | Speros and Rossini, 1960 | ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
39.1 | 50. | Thermodynamics Research Center, 1997 | p=1 bar.; GT |
59.1 | 100. | ||
81.1 | 150. | ||
105.9 | 200. | ||
145.6 | 273.15 | ||
159.3 | 298.15 | ||
160.4 | 300. | ||
212.3 | 400. | ||
256.2 | 500. | ||
291.8 | 600. | ||
320.7 | 700. | ||
344.5 | 800. | ||
364.3 | 900. | ||
381.0 | 1000. | ||
395. | 1100. | ||
407. | 1200. | ||
418. | 1300. | ||
426. | 1400. | ||
434. | 1500. |
Reaction 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
C11H9- + =
By formula: C11H9- + H+ = C11H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1565. ± 8.8 | kJ/mol | G+TS | Bartmess and Griffiths, 1990 | gas phase; Isomer 1-methylene-1,4-dihydronaphthalene: ΔG=349.0±2.0, ΔS=27±2, ΔH=357.1; B |
ΔrH° | 1551. ± 10. | kJ/mol | TDEq | Meot-ner, Liebman, et al., 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1531. ± 8.4 | kJ/mol | IMRE | Bartmess and Griffiths, 1990 | gas phase; Isomer 1-methylene-1,4-dihydronaphthalene: ΔG=349.0±2.0, ΔS=27±2, ΔH=357.1; B |
ΔrG° | 1516. ± 8.4 | kJ/mol | TDEq | Meot-ner, Liebman, et al., 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
By formula: C11H10+ + C11H10 = (C11H10+ • C11H10)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 78.7 | kJ/mol | PHPMS | El-Shall and Meot-Ner (Mautner), 1987 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 126. | J/mol*K | PHPMS | El-Shall and Meot-Ner (Mautner), 1987 | gas phase; M |
By formula: C6H7N+ + C11H10 = (C6H7N+ • C11H10)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 66.1 | kJ/mol | PHPMS | El-Shall and Meot-Ner (Mautner), 1987 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 105. | J/mol*K | PHPMS | El-Shall and Meot-Ner (Mautner), 1987 | gas phase; M |
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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LL - Sharon G. Lias and Joel F. Liebman
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 C11H10+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 7.96 ± 0.03 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 834.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 805.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
<0.16 ± 0.12 | ECD | Wojnarovits and Foldiak, 1981 | EA is an upper limit: Chen and Wentworth, 1989. G3MP2B3 calculations indicate an EA of ca. -0.1 eV, anion unbound.; B |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
831.4 | Aue, Guidoni, et al., 2000 | Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM |
Gas basicity at 298K
Gas basicity (review) (kJ/mol) | Reference | Comment |
---|---|---|
803.3 | Aue, Guidoni, et al., 2000 | Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.90 ± 0.02 | PI | Gotkis and Lifshitz, 1993 | LL |
8.50 ± 0.05 | EI | Loudon and Mazengo, 1974 | LLK |
7.98 | CTS | Pitt, Carey, et al., 1972 | LLK |
7.80 ± 0.03 | EI | Bonnier, Gelus, et al., 1965 | RDSH |
7.98 | CTS | Kinoshita, 1962 | RDSH |
7.96 ± 0.01 | PI | Watanabe, 1957 | RDSH |
8.01 ± 0.03 | PE | Heilbronner, Hoshi, et al., 1976 | Vertical value; LLK |
7.95 | PE | Heilbronner, Hornung, et al., 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C11H9+ | 12.1 ± 0.1 | H | TRPI | Gotkis and Lifshitz, 1993 | LL |
C11H9+ | 10.2 ± 0.2 | H | PI | Huang and Dunbar, 1990 | LL |
C11H9+ | 13.2 ± 0.2 | H | EI | Loudon and Mazengo, 1974 | LLK |
C11H9+ | 12.4 ± 0.1 | H | EI | Nounou, 1966 | RDSH |
De-protonation reactions
C11H9- + =
By formula: C11H9- + H+ = C11H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1565. ± 8.8 | kJ/mol | G+TS | Bartmess and Griffiths, 1990 | gas phase; Isomer 1-methylene-1,4-dihydronaphthalene: ΔG=349.0±2.0, ΔS=27±2, ΔH=357.1; B |
ΔrH° | 1551. ± 10. | kJ/mol | TDEq | Meot-ner, Liebman, et al., 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1531. ± 8.4 | kJ/mol | IMRE | Bartmess and Griffiths, 1990 | gas phase; Isomer 1-methylene-1,4-dihydronaphthalene: ΔG=349.0±2.0, ΔS=27±2, ΔH=357.1; B |
ΔrG° | 1516. ± 8.4 | kJ/mol | TDEq | Meot-ner, Liebman, et al., 1988 | gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B |
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 | NIST Mass Spectrometry Data Center, 1998. |
NIST MS number | 291511 |
UV/Visible spectrum
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Download spectrum in JCAMP-DX format.
Source | Adams and Richardson, 1951 |
---|---|
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. 580 |
Instrument | Beckman DU |
Melting point | -30.4 |
Boiling point | 244.7 |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Speros and Rossini, 1960
Speros, D.M.; Rossini, F.D.,
Heats of combustion and formation of naphthalene, the two methylnaphthalenes, cis and trans decahydronaphthalene and related compounds,
J. Phys. Chem., 1960, 64, 1723-1727. [all data]
Thermodynamics Research Center, 1997
Thermodynamics Research Center,
Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]
Bartmess and Griffiths, 1990
Bartmess, J.E.; Griffiths, S.S.,
Tautomerization Energetics of Benzoannelated Toluenes,
J. Am. Chem. Soc., 1990, 112, 8, 2932, https://doi.org/10.1021/ja00164a014
. [all data]
Meot-ner, Liebman, et al., 1988
Meot-ner, M.; Liebman, J.F.; Kafafi, S.A.,
Ionic Probes of Aromaticity in Annelated Rings,
J. Am. Chem. Soc., 1988, 110, 18, 5937, https://doi.org/10.1021/ja00226a001
. [all data]
Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B.,
Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine,
J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z
. [all data]
El-Shall and Meot-Ner (Mautner), 1987
El-Shall, M.S.; Meot-Ner (Mautner), M.,
Ionic Charge Transfer Complexes. 3. Delocalised pi Systems as Electron Acceptors and Donors,
J. Phys. Chem., 1987, 91, 5, 1088, https://doi.org/10.1021/j100289a017
. [all data]
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]
Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G.,
Electron capture detection of aromatic hydrocarbons,
J. Chromatogr. Sci., 1981, 206, 511. [all data]
Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E.,
Experimental Determination of Electron Affinities of Organic Molecules,
Mol. Cryst. Liq. Cryst., 1989, 171, 271. [all data]
Aue, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D.,
Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons,
Int. J. Mass Spectrom., 2000, 201, 283. [all data]
Gotkis and Lifshitz, 1993
Gotkis, I.; Lifshitz, C.,
Time-dependent mass spectra and breakdown graphs. 16 - The methylnaphthalenes,
Org. Mass Spectrom., 1993, 28, 372. [all data]
Loudon and Mazengo, 1974
Loudon, A.G.; Mazengo, R.Z.,
Steric strain and electron-impact. The behaviour of some n, n'-dimethyl- 1,1-binaphthyls, some n, n'-dimethylbiphenyls and model compounds,
Org. Mass Spectrom., 1974, 8, 179. [all data]
Pitt, Carey, et al., 1972
Pitt, C.G.; Carey, R.N.; Toren, E.C.,
Nature of the electronic interactions in aryl-substituted polysilanes,
J. Am. Chem. Soc., 1972, 94, 3806. [all data]
Bonnier, Gelus, et al., 1965
Bonnier, J.-M.; Gelus, M.; Nounou, P.,
Contribution a l'etude de l'effet inductif et de l'effet d'hyperconjugaison dans quelques methylaromatiques,
J. Chim. Phys., 1965, 10, 1191. [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]
Watanabe, 1957
Watanabe, K.,
Ionization potentials of some molecules,
J. Chem. Phys., 1957, 26, 542. [all data]
Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K.,
Alkyl-induced, natural hypsochromic shifts of the 2A←2X and 2B←2X transitions of azulene and naphthalene radical cations,
Nouv. J. Chim., 1976, 1, 105. [all data]
Heilbronner, Hornung, et al., 1972
Heilbronner, E.; Hornung, V.; Pinkerton, F.H.; Thames, S.F.,
31. Photoelectron spectra of azabenzenes and azanaphthalenes: III. The orbital sequence in methyl- and trimethylsilyl- substituted pyridines,
Helv. Chim. Acta, 1972, 55, 289. [all data]
Huang and Dunbar, 1990
Huang, F.-S.; Dunbar, R.C.,
Time-resolved photodissociation of methylnaphthalene ion. An illustration of kinetic shifts in large-ion dissociations,
J. Am. Chem. Soc., 1990, 112, 8167. [all data]
Nounou, 1966
Nounou, P.,
Etude des composes aromatiques par spectrometrie de masse. I. Mesure des potentials d'ionisation et d'apparition par la methode du potential retardateur et interpretation des courbes d'ionisation differentielle,
J. Chim. Phys., 1966, 63, 994. [all data]
Adams and Richardson, 1951
Adams, N.G.; Richardson, D.M.,
Aromatic hydrocarbons in some diesel fuel fractions. Ultraviolet spectrometric identification,
Anal. Chem., 1951, 23, 1, 129-133. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas EA Electron affinity IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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