Benzyl methyl ketone

• Formula: C₉H₁₀O
• Molecular weight: 134.1751
• IUPAC Standard InChI: InChI=1S/C9H10O/c1-8(10)7-9-5-3-2-4-6-9/h2-6H,7H2,1H3 Copy

  
• IUPAC Standard InChIKey: QCCDLTOVEPVEJK-UHFFFAOYSA-N Copy
• CAS Registry Number: 103-79-7
• 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: 2-Propanone, 1-phenyl-; Methyl benzyl ketone; Phenyl-2-propanone; Phenylacetone; 1-Phenyl-2-propanone; 3-Phenyl-2-propanone; α-Phenylacetone; Phenylmethyl methyl ketone; P2P; NSC 9827; 1-Phenylpropan-2-one; Fenproporex-M (desamino-oxo-); benzylmethylketon
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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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

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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

C₉H₉O^- +  =

By formula: C₉H₉O^- + H⁺ = C₉H₁₀O

 +  = ( • )

By formula: Cl^- + C₉H₁₀O = (Cl^- • C₉H₁₀O)

Free energy of reaction

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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₉H₁₀O⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₉H₉O^- +  =

By formula: C₉H₉O^- + H⁺ = C₉H₁₀O

Ion clustering 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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = ( • )

By formula: Cl^- + C₉H₁₀O = (Cl^- • C₉H₁₀O)

Free energy of reaction

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

Kovats' RI, non-polar column, isothermal

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

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

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, temperature ramp

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References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, Notes

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

Nicholson, Szwarc, et al., 1954
Nicholson, G.R.; Szwarc, M.; Taylor, J.W., The heats of formation of diacetyl and of benzyl methyl ketone in the vapour phase, J. Chem. Soc., 1954, 2767-2769. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [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]

Centineo, Fragala, et al., 1978
Centineo, G.; Fragala, I.; Bruno, G.; Spampinato, S., Photoelectron spectroscopy of benzophenone, acetophenone and their ortho-alkyl derivatives, J. Mol. Struct., 1978, 44, 203. [all data]

Foffani, Pignataro, et al., 1963
Foffani, A.; Pignataro, S.; Cantone, B.; Grasso, F., Mass spectra of diazocompounds. I. Diazocarbonyl compounds, Nuovo Cimento, 1963, 29, 918. [all data]

Wehrli and Kováts, 1959
Wehrli, A.; Kováts, E., Gas-chromatographische Charakterisierung ogranischer Verbindungen. Teil 3: Berechnung der Retentionsindices aliphatischer, alicyclischer und aromatischer Verbindungen, Helv. Chim. Acta, 1959, 7, 7, 2709-2736, https://doi.org/10.1002/hlca.19590420745 . [all data]

Ádámová, Orinák, et al., 2005
Ádámová, M.; Orinák, A.; Halás, L., Retention indices as identification tool in pyrolysis-capillary gas chromatography, J. Chromatogr. A, 2005, 1087, 1-2, 131-141, https://doi.org/10.1016/j.chroma.2005.01.003 . [all data]

Adamiec, Cejpek, et al., 2001
Adamiec, J.; Cejpek, K.; Rossner, J.; Velisek, J., Novel Strecker degradation products of tyrosine and dihydroxyphenylalanine, Czech. J. Food. Sci., 2001, 19, 1, 13-18. [all data]

Baltes and Mevissen, 1988
Baltes, W.; Mevissen, L., Model reactions on roast aroma formation. VI. Volatile reaction products from the reaction of phenylalanine with glucose during cooking and roasting, Z. Lebensm. Unters. Forsch., 1988, 187, 3, 209-214, https://doi.org/10.1007/BF01043341 . [all data]

Ferhat, Tigrine-Kordjani, et al., 2007
Ferhat, M.A.; Tigrine-Kordjani, N.; Chemat, S.; Meklati, B.Y.; Chemat, F., Rapid Extraction of Volatile Compounds Using a New Simultaneous Microwave Distillation: Solvent Extraction Device, Chromatographia, 2007, 65, 3-4, 217-222, https://doi.org/10.1365/s10337-006-0130-5 . [all data]

Tigrine-Kordiani, Meklati, et al., 2006
Tigrine-Kordiani, N.; Meklati, B.Y.; Chemat, F., Abalysis by gas chromatography - mass spectrometry of the essential oil of Zygophyllum album L., an aromatic and medicinal plant growing in Algeria, Int. J. Aromatherapy, 2006, 16, 3-4, 187-191, https://doi.org/10.1016/j.ijat.2006.09.008 . [all data]

Robacker and Bartelt, 1997
Robacker, D.C.; Bartelt, R.J., Chemicals attractive to Mexican fruit fly from Klebsiella pneumoniae and Citrobacter freundii cultures sampled by solid-phase microextraction MICROEXTRACTION, J. Chem. Ecol., 1997, 23, 12, 2897-2915, https://doi.org/10.1023/A:1022579414233 . [all data]

Flath, Matsumoto, et al., 1989
Flath, R.A.; Matsumoto, K.E.; Binder, R.G.; Cunningham, R.T.; Mon, T.R., Effect of pH on the volatiles of hydrolyzed protein insect baits, J. Agric. Food Chem., 1989, 37, 3, 814-819, https://doi.org/10.1021/jf00087a053 . [all data]

Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A., New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments, Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]

Zenkevich, 1996
Zenkevich, I.G., Informational Maitenance of Gas Chromatographic Identification of Organic Compounds in Ecoanalytical Investigations, Z. Anal. Chem., 1996, 51, 11, 1140-1148. [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

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• Symbols used in this document:
  

  AE	Appearance energy
  T	Temperature
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

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