Benzoic acid, 2,3-dimethyl-
- Formula: C9H10O2
- Molecular weight: 150.1745
- IUPAC Standard InChIKey: RIZUCYSQUWMQLX-UHFFFAOYSA-N
- CAS Registry Number: 603-79-2
- 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: Hemellitic acid; 2,3-Dimethylbenzoic acid
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -82.65 ± 0.41 | kcal/mol | Ccb | Colomina, Jimenez, et al., 1984 | see Colomina, Perez-Ossorio, et al., 1961 and Colomina, Perez Ossorio, et al., 1959; ALS |
ΔfH°gas | -82.65 | kcal/mol | N/A | Corral, 1960 | Value computed using ΔfHsolid° value of -450.4±1.0 kj/mol from Corral, 1960 and ΔsubH° value of 104.6 kj/mol from Colomina, Jimenez, et al., 1984.; DRB |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -107.6 ± 0.41 | kcal/mol | Ccb | Colomina, Jimenez, et al., 1984 | see Colomina, Perez-Ossorio, et al., 1961 and Colomina, Perez Ossorio, et al., 1959; ALS |
ΔfH°solid | -107.65 ± 0.23 | kcal/mol | Ccb | Corral, 1960 | Different experiments; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1080.40 ± 0.19 | kcal/mol | Ccb | Corral, 1960 | Different experiments; Corresponding ΔfHºsolid = -107.64 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
51.70 | 299.65 | Colomina, Jimenez, et al., 1984 | DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 416.7 | K | N/A | Birch, Dean, et al., 1949 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 25.00 ± 0.1 | kcal/mol | V | Colomina, Jimenez, et al., 1984 | see Colomina, Perez-Ossorio, et al., 1961 and Colomina, Perez Ossorio, et al., 1959; ALS |
ΔsubH° | 25.00 | kcal/mol | N/A | Colomina, Jimenez, et al., 1984 | DRB |
ΔsubH° | 25.00 ± 0.1 | kcal/mol | ME | Colomina, Jimenez, et al., 1984 | Based on data from 316. to 337. K.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
24.45 ± 0.1 | 326. | ME | Colomina, Jimenez, et al., 1984 | Based on data from 316. to 337. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
4.37 | 417.6 | Belhachemi, Ufnalsky, et al., 1996 | AC |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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: 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
C9H9O2- + =
By formula: C9H9O2- + H+ = C9H10O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 339.1 ± 2.1 | kcal/mol | G+TS | Decouzon, Ertl, et al., 1993 | gas phase; relative to benzoate at 333.0 kcal/mol |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 332.1 ± 2.0 | kcal/mol | IMRE | Decouzon, Ertl, et al., 1993 | gas phase; relative to benzoate at 333.0 kcal/mol |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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: John E. Bartmess
De-protonation reactions
C9H9O2- + =
By formula: C9H9O2- + H+ = C9H10O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 339.1 ± 2.1 | kcal/mol | G+TS | Decouzon, Ertl, et al., 1993 | gas phase; relative to benzoate at 333.0 kcal/mol |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 332.1 ± 2.0 | kcal/mol | IMRE | Decouzon, Ertl, et al., 1993 | gas phase; relative to benzoate at 333.0 kcal/mol |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
View spectrum image in SVG format.
Download spectrum in JCAMP-DX format.
Owner | SRD/NIST Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | EPA-IR VAPOR PHASE LIBRARY |
State | gas |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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 | Japan AIST/NIMC Database- Spectrum MS-IW-4890 |
NIST MS number | 238485 |
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, 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.
Colomina, Jimenez, et al., 1984
Colomina, M.; Jimenez, P.; Roux, M.V.; Turrion, C.,
Thermochemical properties of benzoic acid derivatives. XI. Vapour pressures and enthalpies of sublimation and formation of the six dimethylbenzoic acids,
J. Chem. Thermodyn., 1984, 16, 1121-1127. [all data]
Colomina, Perez-Ossorio, et al., 1961
Colomina, M.; Perez-Ossorio, R.; Boned, M.L.; Panea, M.; Turrion, C.,
Investigaciones termoquimicas sobre los acidos alquilbenzoicos. II. Acidos dimetrilbenzoicos,
Anal. Fisc. Quim. B, 1961, 57, 665-672. [all data]
Colomina, Perez Ossorio, et al., 1959
Colomina, M.; Perez Ossorio, R.; Boned, M.L.; Panea, M.; Turrion, C.,
Thermochemical investigations on methylsubstituted benzoic acids, Rpt. for the U.S. Dept. of the Army, European Research Office contract no. DA-91-508-EUC-358 by Instituto de Quimica Fisica Madrid, Spain, 1959, 1-36. [all data]
Corral, 1960
Corral, L.B.,
Investigaciones termoquimicas sobre los acidos toluicos y dimetilbenzoicos,
Rev. R. Acad. Cienc., 1960, 54, 365-403. [all data]
Birch, Dean, et al., 1949
Birch, S.F.; Dean, R.A.; Fidler, F.A.; Lowry, R.A.,
The preparation of the c(10) monocyclic aromatic hydrocarbons,
J. Am. Chem. Soc., 1949, 71, 1362. [all data]
Belhachemi, Ufnalsky, et al., 1996
Belhachemi, B.; Ufnalsky, W.; Derriche, Z.,
Determination of melting enthalpies and solubility curves in n-hexane of 2,3- and 3,5-dimethyl benzoic acids. Comparison with UNIFAC calculations,
J. Chim. Phys. Phys.-Chim. Biol., 1996, 93, 6, 1117. [all data]
Decouzon, Ertl, et al., 1993
Decouzon, M.; Ertl, P.; Exner, O.; Gal, J.F.; Maria, P.C.,
Concepts of Sterically Hindered Resonance and Buttressing Effect - Gas-Phase Acidities of Methyl-Substituted Benzoic Acids and Basicities of,
J. Am. Chem. Soc., 1993, 115, 25, 12071, https://doi.org/10.1021/ja00078a052
. [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, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid Tfus Fusion (melting) point 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.