Naphthalene
- Formula: C10H8
- Molecular weight: 128.1705
- IUPAC Standard InChIKey: UFWIBTONFRDIAS-UHFFFAOYSA-N
- CAS Registry Number: 91-20-3
- 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. - Isotopologues:
- Other names: Albocarbon; Dezodorator; Moth flakes; Naphthalin; Naphthaline; Naphthene; Tar camphor; White tar; Camphor tar; Moth balls; Naftalen; NCI-C52904; Mighty 150; Mighty RD1; Rcra waste number U165; UN 1334; UN 2304; NSC 37565
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Gas phase ion energetics data
Go To: Top, Ion clustering 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 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
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 C10H8+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.144 ± 0.001 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 802.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 779.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
-0.2 | LPES | Lyapustina, Xu, et al., 2000 | Extrapolated from EAs of solvation series naphthalene-...(H2O)n; B |
-0.18 | N/A | Song, Han, et al., 2002 | Extrapolated from LPES EAs of (naphthalene)n; B |
-0.200 ± 0.050 | LPES | Schiedt, Knott, et al., 2000 | Extrapolated from EAs of (H2O)n..naphthalene-. series; B |
-0.1908 | ETS | Burrow, Michejda, et al., 1987 | The question of whether the naphthalene radical anion is bound or not has not been settled; B |
0.140 ± 0.050 | ECD | Zlatkis, Lee, et al., 1983 | However, see Heinis, Chowdhury, et al., 1993 for a discussion; it may not be bound.; B |
<0.134 ± 0.043 | ECD | Wojnarovits and Foldiak, 1981 | EA is an upper limit: Chen and Wentworth, 1989. G3MP2B3 calculations indicate an EA of ca. -0.3 eV, anion unbound.; B |
0.1480 ± 0.0060 | ECD | Becker and Chen, 1966 | B |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
800.0 | 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 |
---|---|---|
774.5 | Aue, Guidoni, et al., 2000 | Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM |
Ionization energy determinations
Appearance energy determinations
De-protonation reactions
C10H7- + =
By formula: C10H7- + H+ = C10H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1649. ± 5.0 | kJ/mol | Bran | Reed and Kass, 2000 | gas phase; B |
ΔrH° | 1649. ± 5.0 | 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 |
ΔrH° | 1648. ± 21. | kJ/mol | CIDC | Lardin, Squires, et al., 2001 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1613. ± 5.4 | kJ/mol | H-TS | Reed and Kass, 2000 | gas phase; B |
ΔrG° | 1606. ± 5.0 | 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 |
ΔrG° | 1613. ± 21. | kJ/mol | H-TS | Lardin, Squires, et al., 2001 | gas phase; B |
C10H7- + =
By formula: C10H7- + H+ = C10H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1655. ± 5.4 | kJ/mol | Bran | Reed and Kass, 2000 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1619. ± 5.9 | kJ/mol | H-TS | Reed and Kass, 2000 | gas phase; B |
Ion clustering data
Go To: Top, 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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: C6H7N+ + C10H8 = (C6H7N+ • C10H8)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 64.4 | kJ/mol | PHPMS | El-Shall and Meot-Ner (Mautner), 1987 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | N/A | El-Shall and Meot-Ner (Mautner), 1987 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
31. | 324. | PHPMS | El-Shall and Meot-Ner (Mautner), 1987 | gas phase; Entropy change calculated or estimated; M |
By formula: C10H8+ + C10H8 = (C10H8+ • C10H8)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 74.5 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 120. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; M |
By formula: C10H8NO- + 2C10H8 = C20H16NO-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 99.6 ± 9.6 | kJ/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
By formula: C10H9+ + C10H8 = (C10H9+ • C10H8)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 59.0 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 130. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; M |
By formula: C12H8+ + C10H8 = (C12H8+ • C10H8)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 52.7 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 120. | J/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 21. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
By formula: C12H9+ + C10H8 = (C12H9+ • C10H8)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 58.2 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 120. | J/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 27. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
By formula: H2O3- + C10H8 + H2O = C10H10O3-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 158. ± 9.6 | kJ/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
By formula: H4O4- + C10H8 + 2H2O = C10H12O4-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 219. ± 9.6 | kJ/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
+ = C10H8NO-
By formula: NO- + C10H8 = C10H8NO-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 60.7 ± 9.6 | kJ/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
+ = C10H8O2-
By formula: O2- + C10H8 = C10H8O2-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 92.5 ± 9.6 | kJ/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
Mass spectrum (electron ionization)
Go To: Top, Gas phase ion energetics data, Ion clustering 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 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 | Japan AIST/NIMC Database- Spectrum MS-NW-1434 |
NIST MS number | 228342 |
References
Go To: Top, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
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. [all data]
Lyapustina, Xu, et al., 2000
Lyapustina, S.A.; Xu, S.K.; Nilles, J.M.; Bowen, K.H.,
Solvent-induced stabilization of the naphthalene anion by water molecules: A negative cluster ion photoelectron spectroscopic study,
J. Chem. Phys., 2000, 112, 15, 6643-6648, https://doi.org/10.1063/1.481237
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Song, Han, et al., 2002
Song, J.K.; Han, S.Y.; Chu, I.H.; Kim, J.H.; Kim, S.K.; Lyapustina, S.A.; Xu, S.J.; Nilles, J.M.; Bowen, K.H.,
Photoelectron spectroscopy of naphthalene cluster anions,
J. Chem. Phys., 2002, 116, 11, 4477-4481, https://doi.org/10.1063/1.1449869
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Schiedt, Knott, et al., 2000
Schiedt, J.; Knott, W.J.; Le Barbu, K.; Schlag, E.W.; Weinkauf, R.,
Microsolvation of similar-sized aromatic molecules: Photoelectron spectroscopy of bithiophene-, azulene-, and naphthalene-water anion clusters,
J. Chem. Phys., 2000, 113, 21, 9470-9478, https://doi.org/10.1063/1.1319874
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Constant current linearization for determination of electron capture mechanisms,
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Electron Affinities of Naphthalene, Anthracene and Substituted Naphthalenes and Anthracenes,
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Electron capture detection of aromatic hydrocarbons,
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Experimental Determination of Electron Affinities of Organic Molecules,
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Extension of Electron Affinities and Ionization Potentials of Aromatic Hydrocarbons,
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Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons,
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Ion thermochemistry of low volatility compounds in the gas phase. 3. Polycyclic aromatics: Ionization energies, proton, and hydrogen affinities. Extrapolations to graphite,
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Charge transfer in organic solids, induced by light,
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Experimental determination of the alpha and beta C-H bond dissociation energies in naphthalene,
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Determination of the electron affinities of alpha- and beta- naphthyl radicals using the kinetic method with full entropy analysis. The C-H bond dissociation energies of naphthalene,
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Le Barbu, Schiedt, et al., 2002
Le Barbu, K.; Schiedt, J.; Weinkauf, R.; Schlag, E.W.; Nilles, J.M.; Xu, S.J.; Thomas, O.C.; Bowen, K.H.,
Microsolvation of small anions by aromatic molecules: An exploratory study,
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. [all data]
Notes
Go To: Top, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy T Temperature 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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