Naphthalene, 2-bromo-
- Formula: C10H7Br
- Molecular weight: 207.067
- IUPAC Standard InChIKey: APSMUYYLXZULMS-UHFFFAOYSA-N
- CAS Registry Number: 580-13-2
- 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: β-Bromonaphthalene; β-Naphthyl bromide; 2-Bromonaphthalene; 2-Naphthyl bromide
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 41.97 ± 0.55 | kcal/mol | Ccr | Ribeiro da Silva, Ferrao, et al., 1993 |
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 | 22.6 ± 0.50 | kcal/mol | Ccr | Ribeiro da Silva, Ferrao, et al., 1993 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1202.2 ± 0.41 | kcal/mol | Ccr | Ribeiro da Silva, Ferrao, et al., 1993 |
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
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 554.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 554.15 | K | N/A | Cooper, Crowne, et al., 1967 | Uncertainty assigned by TRC = 0.7 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 332. | K | N/A | Khanna, Khetarpal, et al., 1981 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 15.8 ± 0.1 | kcal/mol | GS | Verevkin, 2003 | Based on data from 330. to 360. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 19.4 ± 0.24 | kcal/mol | C | Ribeiro da Silva, Ferrao, et al., 1993 | ALS |
ΔsubH° | 19.4 ± 0.24 | kcal/mol | C | da Silva, 1993 | AC |
ΔsubH° | 15. ± 1. | kcal/mol | TE,ME | Ferro, Piacente, et al., 1981 | Based on data from 275. to 378. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.2 | 354. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 330. to 378. K.; AC |
9.66 | 340. | ME,TE | Ferro, Piacente, et al., 1981 | Based on data from 322. to 359. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.44 | 329. | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
4.324 | 319. | Domalski and Hearing, 1996 | CAL |
10.46 | 329. |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
1.379 | 319. | crystaline, III | crystaline, I | Chanh, Haget, et al., 1981 | DH |
3.4417 | 329. | crystaline, I | liquid | Chanh, Haget, et al., 1981 | A second order transition occurs between crystalline phases c,I and c,II over the temperature range 275 to 319 K.; DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
4.324 | 319. | crystaline, III | crystaline, I | Chanh, Haget, et al., 1981 | DH |
10.46 | 329. | crystaline, I | liquid | Chanh, Haget, et al., 1981 | A; DH |
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 by: John E. Bartmess
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
By formula: C10H6Br- + H+ = C10H7Br
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 390.3 ± 3.3 | kcal/mol | Bran | Wenthold and Squires, 1995 | gas phase; By HO- cleavage of substituted silanes |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 382.5 ± 3.4 | kcal/mol | H-TS | Wenthold and Squires, 1995 | gas phase; By HO- cleavage of substituted silanes |
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 as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.18 ± 0.03 | TRPI | Gotkis, Naor, et al., 1993 | LL |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C10H7+ | 11.29 | Br | DER | Gotkis, Naor, et al., 1993 | LL |
C10H7+ | 12.1 ± 0.1 | Br | TRPI | Gotkis, Naor, et al., 1993 | LL |
De-protonation reactions
By formula: C10H6Br- + H+ = C10H7Br
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 390.3 ± 3.3 | kcal/mol | Bran | Wenthold and Squires, 1995 | gas phase; By HO- cleavage of substituted silanes; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 382.5 ± 3.4 | kcal/mol | H-TS | Wenthold and Squires, 1995 | gas phase; By HO- cleavage of substituted silanes; B |
IR 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.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 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 |
State | gas |
Instrument | HP-GC/MS/IRD |
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.
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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Source | McClure, Blake, et al., 1954 |
---|---|
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. 994 |
Instrument | n.i.g. |
Melting point | 59 |
Boiling point | 281.5 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Ribeiro da Silva, Ferrao, et al., 1993
Ribeiro da Silva, M.A.V.; Ferrao, M.L.C.C.H.; Lopes, A.J.M.,
Enthalpies of combustion of each of the two bromonaphthalenes,
J. Chem. Thermodyn., 1993, 25, 229-235. [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]
Cooper, Crowne, et al., 1967
Cooper, A.R.; Crowne, C.W.P.; Farrell, P.G.,
Gas-Liquid Chromatographic Studies of Electron-Donor-Acceptor Systems,
Trans. Faraday Soc., 1967, 63, 447. [all data]
Khanna, Khetarpal, et al., 1981
Khanna, M.S.; Khetarpal, S.C.; Lal, K.; Bhatnagar, H.L.,
Thermodynamic studies on melting of some alpha- and beta-halogen derivatives of napthalene,
Indian J. Chem> Sect. A, 1981, 20, 544. [all data]
Verevkin, 2003
Verevkin, Sergey P.,
Vapor pressures and enthalpies of vaporization of a series of 1- and 2-halogenated naphthalenes,
The Journal of Chemical Thermodynamics, 2003, 35, 8, 1237-1251, https://doi.org/10.1016/S0021-9614(03)00051-X
. [all data]
da Silva, 1993
da Silva, M.,
Enthalpies of combustion of each of the two bromonaphthalenes,
Z. Chem., 1993, 25, 2, 229-235, https://doi.org/10.1006/jcht.1993.1022
. [all data]
Ferro, Piacente, et al., 1981
Ferro, D.; Piacente, V.; Pelino, M.,
Rev. Roum. Chim., 1981, 26, 9. [all data]
Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R.,
Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Chanh, Haget, et al., 1981
Chanh, N.B.; Haget, Y.; Meresse, A.; Louer, D.; Shirley, R.,
Destructive and nondestructive phase transitions of the molecular crystal 2-bromonaphthalene,
J. Phys. Chem. Solids, 1981, 42, 217-225. [all data]
Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R.,
Determination of the gas-phase acidities of halogen-substituted aromatic compounds using the silane-cleavage method,
J. Mass Spectrom., 1995, 30, 1, 17, https://doi.org/10.1002/jms.1190300105
. [all data]
Gotkis, Naor, et al., 1993
Gotkis, Y.; Naor, M.; Laskin, J.; Lifshitz, C.; Faulk, J.D.; Dunbar, R.C.,
Time-resolved dissociation of bromonaphthalene ion studied by TPIMS and TRPD. Heat of formation of naphthyl ion,
J. Am. Chem. Soc., 1993, 115, 7402. [all data]
McClure, Blake, et al., 1954
McClure, D.S.; Blake, N.W.; Hanst, P.L.,
Singlet-triplet absorption bands in some halogen substituted aromatic compounds,
J. Chem. Phys., 1954, 22, 2, 255-258. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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