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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Reaction thermochemistry data
Go To: Top, 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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
C10H7- + =
By formula: C10H7- + H+ = C10H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 394.2 ± 1.2 | kcal/mol | Bran | Reed and Kass, 2000 | gas phase; B |
ΔrH° | 394.2 ± 1.2 | kcal/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° | 394.0 ± 5.0 | kcal/mol | CIDC | Lardin, Squires, et al., 2001 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 385.6 ± 1.3 | kcal/mol | H-TS | Reed and Kass, 2000 | gas phase; B |
ΔrG° | 383.8 ± 1.2 | kcal/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° | 385.4 ± 5.1 | kcal/mol | H-TS | Lardin, Squires, et al., 2001 | gas phase; B |
By formula: C6H7N+ + C10H8 = (C6H7N+ • C10H8)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15.4 | kcal/mol | PHPMS | El-Shall and Meot-Ner (Mautner), 1987 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 26. | cal/mol*K | N/A | El-Shall and Meot-Ner (Mautner), 1987 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
7.3 | 324. | PHPMS | El-Shall and Meot-Ner (Mautner), 1987 | gas phase; Entropy change calculated or estimated; M |
By formula: C12H8+ + C10H8 = (C12H8+ • C10H8)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 12.6 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 28. | cal/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 5.1 | kcal/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° | 13.9 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 28. | cal/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 6.4 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated; M |
By formula: 2H2 + C10H8 = C10H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -29.8 | kcal/mol | Eqk | Frye and Weitkamp, 1969 | gas phase; ALS |
ΔrH° | -28.8 ± 1.2 | kcal/mol | Eqk | Wilson, Caflisch, et al., 1958 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -32.0 ± 1.2 kcal/mol; At 400 K; ALS |
By formula: C10H8 = C10H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -59.4 ± 1.9 | kcal/mol | Eqk | Dreeskamp, Kapahnke, et al., 1988 | liquid phase; solvent: Heptane; Isomerization; ALS |
ΔrH° | -59.6 ± 1.9 | kcal/mol | Ciso | Grimme and Heinze, 1978 | liquid phase; solvent: Heptane; ALS |
By formula: C10H8+ + C10H8 = (C10H8+ • C10H8)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 17.8 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 29. | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; M |
C10H7- + =
By formula: C10H7- + H+ = C10H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 395.5 ± 1.3 | kcal/mol | Bran | Reed and Kass, 2000 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 386.9 ± 1.4 | kcal/mol | H-TS | Reed and Kass, 2000 | gas phase; B |
By formula: H4O4- + C10H8 + 2H2O = C10H12O4-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 52.3 ± 2.3 | kcal/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
By formula: H2O3- + C10H8 + H2O = C10H10O3-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 37.8 ± 2.3 | kcal/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° | 14.1 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 30. | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; M |
+ = C10H8O2-
By formula: O2- + C10H8 = C10H8O2-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 22.1 ± 2.3 | kcal/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° | 14.5 ± 2.3 | kcal/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
By formula: C10H8NO- + 2C10H8 = C20H16NO-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 23.8 ± 2.3 | kcal/mol | N/A | Le Barbu, Schiedt, et al., 2002 | gas phase; Affinity is difference in EAs of lesser solvated species; B |
By formula: 5H2 + C10H8 = C10H18
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -76.0 | kcal/mol | Eqk | Frye and Weitkamp, 1969 | gas phase; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Reed and Kass, 2000
Reed, D.R.; Kass, S.R.,
Experimental determination of the alpha and beta C-H bond dissociation energies in naphthalene,
J. Mass Spectrom., 2000, 35, 4, 534-539, https://doi.org/10.1002/(SICI)1096-9888(200004)35:4<534::AID-JMS964>3.0.CO;2-T
. [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]
Lardin, Squires, et al., 2001
Lardin, H.A.; Squires, R.R.; Wenthold, P.G.,
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,
J. Mass Spectrom., 2001, 36, 6, 607-615, https://doi.org/10.1002/jms.159
. [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]
Meot-Ner (Mautner), 1980
Meot-Ner (Mautner), M.,
Dimer Cations of Polycyclic Aromatics: Experimental Bonding Energies and Resonance Stabilization,
J. Phys. Chem., 1980, 84, 21, 2724, https://doi.org/10.1021/j100458a012
. [all data]
Frye and Weitkamp, 1969
Frye, C.G.; Weitkamp, A.W.,
Equilibrium hydrogenations of multi-ring aromatics,
J. Chem. Eng. Data, 1969, 14, 372-376. [all data]
Wilson, Caflisch, et al., 1958
Wilson, T.P.; Caflisch, E.G.; Hurley, G.F.,
The naphthalene-tetralin-hydrogen equilibrium at elevated temperature and pressure,
J. Phys. Chem., 1958, 62, 1059. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Dreeskamp, Kapahnke, et al., 1988
Dreeskamp, H.; Kapahnke, P.; Tochtermann, W.,
Photo valence isomerization of sterically strained aromatic hydrocarbons: 8,9-dicarbethoxy[6]paracyclophane,
Radiat. Phys. Chem., 1988, 32, 537-539. [all data]
Grimme and Heinze, 1978
Grimme, W.; Heinze, U.,
Kinetics and enthalpy of isomerization of benzobicyclo[2.2.0]hexa-2,5-diene,
Chem. Ber., 1978, 111, 2563-2570. [all data]
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,
J. Chem. Phys., 2002, 116, 22, 9663-9671, https://doi.org/10.1063/1.1475750
. [all data]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
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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