1,4-Benzenedicarboxylic acid, dimethyl ester
- Formula: C10H10O4
- Molecular weight: 194.1840
- IUPAC Standard InChI: InChI=1S/C10H10O4/c1-13-9(11)7-3-5-8(6-4-7)10(12)14-2/h3-6H,1-2H3
- IUPAC Standard InChIKey: WOZVHXUHUFLZGK-UHFFFAOYSA-N
- CAS Registry Number: 120-61-6
- 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: Terephthalic acid, dimethyl ester; Dimethyl p-phthalate; Dimethyl terephthalate; Dimethyl 1,4-benzenedicarboxylate; Methyl 4-(carbomethoxy)benzoate; Dimethyl p-benzenedicarboxylate; Dimethylester kyseliny isoftalove; DMT; NCI-C50055; Dimethylester kyseliny tereftalove; Dimethyl ester of 1,4-benzenedicarboxylic acid; Terephthalate, dimethyl; 1,4-Benzenedicarboxylic acid, 1,4-dimethyl ester; Methyl p-(methoxycarbonyl)benzoate; NSC 3503; Dimethyl terphthalate
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Gas phase ion energetics data
Go To: Top, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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
Data compiled as indicated in comments:
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 843.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 812.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 0.824 ± 0.087 | IMRE | Mishima, Huh, et al., 1995 | ΔGea(343 K)=-20.2 kcal/mol. Reanchored to EA(PhNO2), Kebarle and Chowdhury, 1987.; B |
| 0.824 ± 0.087 | IMRE | Huh, Kang, et al., 1999 | ΔG(EA) 343K; anchored to ΔG value. Including anchor ΔS, EA is ca. 0.4 kcal/mol more bound.; B |
| 0.640011 | ECD | Kuhn, Levins, et al., 1968 | Done at constant temperature, accuracy uncertain: Chen and Wentworth, 1989;; B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.78 ± 0.03 | EI | Kuhn, Levins, et al., 1968 | RDSH |
IR Spectrum
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compiled by: Coblentz Society, Inc.
- Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)
- SOLID (MULL); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
- SOLID (SPLIT MULL), FLUOROLUBE FOR 3800-1330 CM-1, NUJOL FOR 1330-400 CM-1; DOW FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm-1 resolution
Data compiled by: Timothy J. Johnson, Tanya L. Myers, Yin-Fong Su, Russell G. Tonkyn, Molly Rose K. Kelly-Gorham, and Tyler O. Danby
- solid; Bruker Tensor 37 FTIR
0.96450084, 0.96450084 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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
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-NW-6813 |
| NIST MS number | 228185 |
Gas Chromatography
Go To: Top, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | Ultra-1 | 125. | 1461. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
| Capillary | Ultra-1 | 150. | 1470. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
| Capillary | Ultra-1 | 175. | 1480. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
| Capillary | Ultra-1 | 200. | 1492. | Herrmann, Dufka, et al., 1986 | 25. m/0.20 mm/0.32 μm, N2 |
| Packed | OV-1 | 150. | 1468. | Fedoreev and Maksimov, 1977 | Gaschrom; Column length: 1.5 m |
Kovats' RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | SE-30 | 1475. | Ramsey, Lee, et al., 1980 | He, Chromosorb G HP (80-100 mesh); Column length: 1.5 m; Program: not specified |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | SE-30 | 1469. | Peng, Ding, et al., 1988 | Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min) |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Ultra-ALLOY-5 | 1512. | Tsuge, Ohtan, et al., 2011 | 30. m/0.25 mm/0.25 μm, 40. C @ 2. min, 20. K/min, 320. C @ 13. min |
| Capillary | Ultra-1 | 1468. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Polydimethyl siloxanes | 1473. | Zenkevich, 2003 | Program: not specified |
| Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 1475. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
| Other | Methyl Silicone | 1475. | Ardrey and Moffat, 1981 | Program: not specified |
References
Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Mishima, Huh, et al., 1995
Mishima, M.; Huh, C.; Lee, H.W.; Nakamura, H.; Fujio, M.; Tsuno, Y.,
Electron affinities of acetophenones and methyl benzoates. Varying resonance demand of aromatic radical anions,
Tetrahed. Lett., 1995, 36, 13, 2265, https://doi.org/10.1016/0040-4039(95)00267-G
. [all data]
Kebarle and Chowdhury, 1987
Kebarle, P.; Chowdhury, S.,
Electron affinities and electron transfer reactions,
Chem. Rev., 1987, 87, 513. [all data]
Huh, Kang, et al., 1999
Huh, C.; Kang, C.H.; Lee, H.W.; Nakamura, H.; Mishima, M.; Tsuno, Y.; Yamataka, H.,
Thermodynamic stabilities and resonance demand of aromatic radical anions in the gas phase,
Bull. Chem. Soc. Japan, 1999, 72, 5, 1083-1091, https://doi.org/10.1246/bcsj.72.1083
. [all data]
Kuhn, Levins, et al., 1968
Kuhn, W.F.; Levins, R.J.; Lilly, A.C., Jr.,
Electron affinities and ionization potentials of phthalate compounds,
J. Chem. Phys., 1968, 49, 5550. [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]
Herrmann, Dufka, et al., 1986
Herrmann, F.; Dufka, O.; Churacek, J.,
Fused-Silica Capillary Gas Chromatography-Mass Spectrometry of Some Dicarboxylic Acids Present in Condensation-Type Polymers I. Dimethyl Esters,
J. Chromatogr., 1986, 360, 79-88, https://doi.org/10.1016/S0021-9673(00)91653-4
. [all data]
Fedoreev and Maksimov, 1977
Fedoreev, S.A.; Maksimov, O.B.,
The study of the composition of aromatic esters by gas-liquid chromatography,
Solid Fuel Chem. (Engl. Transl.), 1977, 17-22. [all data]
Ramsey, Lee, et al., 1980
Ramsey, J.D.; Lee, T.D.; Osselton, M.D.; Moffat, A.C.,
Gas-liquid chromatographic retention indices of 296 non-drug substances on SE-30 or OV-1 likely to be encountered in toxicological analyses,
J. Chromatogr., 1980, 184, 2, 185-206, https://doi.org/10.1016/S0021-9673(00)85641-1
. [all data]
Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C.,
Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns,
J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8
. [all data]
Tsuge, Ohtan, et al., 2011
Tsuge, S.; Ohtan, H.; Watanabe, C.,
Pyrolysis - GC/MS Data Book of Synthetic Polymers, Elsevier, 2011, 420. [all data]
Okumura, 1991
Okumura, T.,
retention indices of environmental chemicals on methyl silicone capillary column,
Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333
. [all data]
Zenkevich, 2003
Zenkevich, I.G.,
Criteria for Evaluation of Elution Order of Isomeric Organic Compounds,
Zh. Phys. Khim. (Rus.), 2003, 77, 1, 92-98. [all data]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C.,
Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase,
J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1
. [all data]
Notes
Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
EA Electron affinity - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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