2-Butenoic acid, 3-methyl-

• Formula: C₅H₈O₂
• Molecular weight: 100.1158
• IUPAC Standard InChI: InChI=1S/C5H8O2/c1-4(2)3-5(6)7/h3H,1-2H3,(H,6,7) Copy

  
• IUPAC Standard InChIKey: YYPNJNDODFVZLE-UHFFFAOYSA-N Copy
• CAS Registry Number: 541-47-9
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: Crotonic acid, 3-methyl-; β-Methylcrotonic acid; β,β-Dimethylacrylic acid; Senecioic acid; 3-Methyl-2-butenoic acid; 3-Methylcrotonic acid; 3,3-Dimethylacrylic acid; (CH3)2C=CHCOOH; β,β-Dimethacrylic acid; Senecic acid; Kyselina 3-methyl-2-butenova; 3-Methylbut-2-enoic acid; NSC 2549; 3-methyl-buten-2-oic-acid
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
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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

Enthalpy of vaporization

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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

De-protonation reactions

C₅H₇O₂^- +  =

By formula: C₅H₇O₂^- + H⁺ = C₅H₈O₂

Gas Chromatography

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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

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, polar column, custom temperature program

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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References

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

D'Souza and Teja, 1987
D'Souza, R.; Teja, A.S., The prediction of the vapor pressures of carboxylic acids, Chem. Eng. Commun., 1987, 61, 13. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

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]

Holmes, Terlouw, et al., 1979
Holmes, J.L.; Terlouw, J.K.; Vijfhuizen, P.C.; A'Campo, C., Metastable ion studies XII-Molecular and fragment ion structures for isomeric C₄H₆O₂ acids, Org. Mass Spectrom., 1979, 14, 204. [all data]

Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P., Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria, Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092 . [all data]

Graul, Schnute, et al., 1990
Graul, S.T.; Schnute, M.E.; Squires, R.R., Gas-Phase Acidities of Carboxylic Acids and Alcohols from Collision-Induced Dissociation of Dimer Cluster Ions, Int. J. Mass Spectrom. Ion Proc., 1990, 96, 2, 181, https://doi.org/10.1016/0168-1176(90)87028-F . [all data]

Milos and Radonic, 2000
Milos, M.; Radonic, A., Gas chromatography mass spectral analysis of free and glycosidically bound volatile compounds from Juniperus oxycedrus L. growing wild in Croatia, Food Chem., 2000, 68, 3, 333-338, https://doi.org/10.1016/S0308-8146(99)00192-2 . [all data]

Tret'yakov, 2007
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]

Cantergiani, Brevard, et al., 2001
Cantergiani, E.; Brevard, H.; Krebs, Y.; Feria-Morales, A.; Amadò, R.; Yeretzian, C., Characterisation of the aroma of green Mexican coffee and identification of mouldy/earthy defect, Eur. Food Res. Technol., 2001, 212, 6, 648-657, https://doi.org/10.1007/s002170100305 . [all data]

Birtic, Ginies, et al., 2009
Birtic, S.; Ginies, C.; Causse, M.; Renard, C.M.G.C.; Page, D., Changes in volatiles and glycosides during fruit maturartion of two contrasted tomato (Solanum lycopersicum) lines, J. Agric. Food Chem., 2009, 57, 2, 591-598, https://doi.org/10.1021/jf8023062 . [all data]

Moon and Shibamoto, 2009
Moon, J.-K.; Shibamoto, T., Role of roasting conditions in the profile of volatile flavor chemicals formed from coffee beans, J. Agric. Food Chem., 2009, 57, 13, 5823-5831, https://doi.org/10.1021/jf901136e . [all data]

Wijaya, Ulrich, et al., 2005
Wijaya, C.H.; Ulrich, D.; Lestari, R.; Schippel, K.; Ebert, G., Identification of potent odorants in different cultivars of snake fruit [Salacca zalacca (Gaert.) Voss] using gas chromatography-olfactometry, J. Agric. Food Chem., 2005, 53, 5, 1637-1641, https://doi.org/10.1021/jf048950h . [all data]

Suhardi, Suzuki, et al., 2002
Suhardi, S.; Suzuki, M.; Yoshida, K.; Muto, T.; Fujita, A.; Watanbe, N., Changes in the volatile compounds and in the chemical and physical properties of snake fruit (Salacca edulis Reinw) Cv. Pondoh during maturation, J. Agric. Food Chem., 2002, 50, 26, 7627-7633, https://doi.org/10.1021/jf020620e . [all data]

Kawakami and Kobayashi, 1991
Kawakami, M.; Kobayashi, A., Volatitle constituents of greem mate and roasted mate, J. Agric. Food Chem., 1991, 39, 7, 1275-1279, https://doi.org/10.1021/jf00007a016 . [all data]

Vernin, Metzger, et al., 1988
Vernin, G.; Metzger, J.; Obretenov, T.; Suon, K.-N.; Fraisse, D., GC/MS (EI,PCI,SIM)-data bank analysis of volatile compounds arising from thermal degradation of glucose-valine amadori intermediates in Flavors and Fragrances: A World Perspective. Proceedings of the 10th International Congress of Essential Oils, Fragrances and Flavors, Lawrence,B.M.; Mookherjee,B.D.; Willis,B.J., ed(s)., Elsevier, New York, 1988, 999-1028. [all data]

Andersen J.F., Mikolajczak K.L., et al., 1987
Andersen J.F.; Mikolajczak K.L.; Reed D.K., Analysis of peach bark volatiles and their electroantennogram activity with lesser pechtree borer, Synanthedon pictipes (Grote and Robinson), J. Chem. Ecol., 1987, 13, 11, 2103-2114, https://doi.org/10.1007/BF01012874 . [all data]

Gonzalez-Rios, Suarez-Quiroz, et al., 2007
Gonzalez-Rios, O.; Suarez-Quiroz, M.L.; Boulanger, R.; Barel, M.; Guyot, B.; Guiraud, J.-P.; Schorr-Galindo, S., Impact of ecological post-harvest processing of coffee aroma: II Roasted coffee., J. Food Composition Analysis, 2007, 20, 3-4, 297-307, https://doi.org/10.1016/j.jfca.2006.12.004 . [all data]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References

• Symbols used in this document:
  

  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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