Pyrrole

• Formula: C₄H₅N
• Molecular weight: 67.0892
• IUPAC Standard InChI: InChI=1S/C4H5N/c1-2-4-5-3-1/h1-5H Copy

  
• IUPAC Standard InChIKey: KAESVJOAVNADME-UHFFFAOYSA-N Copy
• CAS Registry Number: 109-97-7
• 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: 1H-Pyrrole; Azole; Divinylenimine; Imidole; Monopyrrole; Pyrrol; 1-Aza-2,4-cyclopentadiene; Divinyleneimine; Parzate; NSC 62777
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • Ion clustering data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Reaction thermochemistry data

Go To: Top, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar

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: C₄H₄N^- + H⁺ = C₄H₅N

CN^- +  = (CN^- • )

By formula: CN^- + C₄H₅N = (CN^- • C₄H₅N)

 +  = ( • )

By formula: F^- + C₄H₅N = (F^- • C₄H₅N)

 +  = ( • )

By formula: Cl^- + C₄H₅N = (Cl^- • C₄H₅N)

Free energy of reaction

HS^- +  = (HS^- • )

By formula: HS^- + C₄H₅N = (HS^- • C₄H₅N)

 +  = ( • )

By formula: C₄H₄N^- + C₄H₅N = (C₄H₄N^- • C₄H₅N)

 +  = ( • )

By formula: C₂H₃O₂^- + C₄H₅N = (C₂H₃O₂^- • C₄H₅N)

(C₄H₅N⁺ • ) +  = (C₄H₅N⁺ • 2)

By formula: (C₄H₅N⁺ • C₄H₅N) + C₄H₅N = (C₄H₅N⁺ • 2C₄H₅N)

Bond type: Charge transfer bond (positive ion)

C₄H₅N⁺ +  = (C₄H₅N⁺ • )

By formula: C₄H₅N⁺ + C₄H₅N = (C₄H₅N⁺ • C₄H₅N)

Bond type: Charge transfer bond (positive ion)

(C₄H₆N⁺ • ) +  = (C₄H₆N⁺ • 2)

By formula: (C₄H₆N⁺ • C₄H₅N) + C₄H₅N = (C₄H₆N⁺ • 2C₄H₅N)

( • ) +  = ( • 2)

By formula: (C₄H₄N^- • C₄H₅N) + C₄H₅N = (C₄H₄N^- • 2C₄H₅N)

C₄H₆N⁺ +  = (C₄H₆N⁺ • )

By formula: C₄H₆N⁺ + C₄H₅N = (C₄H₆N⁺ • C₄H₅N)

( • ) +  = ( • 2)

By formula: (C₂H₃O₂^- • C₄H₅N) + C₄H₅N = (C₂H₃O₂^- • 2C₄H₅N)

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₄H₅N = (CH₆N⁺ • C₄H₅N)

 +  = ( • )

By formula: C₆H₁₁NO₃ + C₄H₅N = (C₆H₁₁NO₃ • C₄H₅N)

( • ) +  = ( • 2)

By formula: (Fe⁺ • C₄H₅N) + C₄H₅N = (Fe⁺ • 2C₄H₅N)

( • ) +  = ( • 2)

By formula: (Cr⁺ • C₄H₅N) + C₄H₅N = (Cr⁺ • 2C₄H₅N)

( • ) +  = ( • 2)

By formula: (Mn⁺ • C₄H₅N) + C₄H₅N = (Mn⁺ • 2C₄H₅N)

( • ) +  = ( • 2)

By formula: (Ni⁺ • C₄H₅N) + C₄H₅N = (Ni⁺ • 2C₄H₅N)

( • ) +  = ( • 2)

By formula: (Co⁺ • C₄H₅N) + C₄H₅N = (Co⁺ • 2C₄H₅N)

( • ) +  = ( • 2)

By formula: (Cu⁺ • C₄H₅N) + C₄H₅N = (Cu⁺ • 2C₄H₅N)

 +  = ( • )

By formula: Li⁺ + C₄H₅N = (Li⁺ • C₄H₅N)

 +  = ( • )

By formula: Na⁺ + C₄H₅N = (Na⁺ • C₄H₅N)

 +  = ( • )

By formula: K⁺ + C₄H₅N = (K⁺ • C₄H₅N)

 +  = ( • )

By formula: V⁺ + C₄H₅N = (V⁺ • C₄H₅N)

 +  = ( • )

By formula: Ni⁺ + C₄H₅N = (Ni⁺ • C₄H₅N)

 +  = ( • )

By formula: W⁺ + C₄H₅N = (W⁺ • C₄H₅N)

 +  = ( • )

By formula: Co⁺ + C₄H₅N = (Co⁺ • C₄H₅N)

 +  = ( • )

By formula: Mo⁺ + C₄H₅N = (Mo⁺ • C₄H₅N)

 +  = ( • )

By formula: Fe⁺ + C₄H₅N = (Fe⁺ • C₄H₅N)

 +  = ( • )

By formula: Cr⁺ + C₄H₅N = (Cr⁺ • C₄H₅N)

 +  = ( • )

By formula: Mn⁺ + C₄H₅N = (Mn⁺ • C₄H₅N)

 +  = ( • )

By formula: Mg⁺ + C₄H₅N = (Mg⁺ • C₄H₅N)

 +  = ( • )

By formula: Al⁺ + C₄H₅N = (Al⁺ • C₄H₅N)

 +  = ( • )

By formula: Cu⁺ + C₄H₅N = (Cu⁺ • C₄H₅N)

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

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

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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Kovats' RI, 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, non-polar column, custom temperature program

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

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

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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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Normal alkane RI, polar column, custom temperature program

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References

Go To: Top, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes

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

Gianola, Ichino, et al., 2004
Gianola, A.J.; Ichino, T.; Hoenigman, R.L.; Kato, S.; Bierbaum, V.M.; Lineberger, W.C., Thermochemistry and electronic structure of the pyrrolyl radical, J. Phys. Chem. A, 2004, 108, 46, 10326-10335, https://doi.org/10.1021/jp047790+ . [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]

Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Khatymov, R.V.; Mazunov, V.A.; Takhistov, V.V.; Travkin, O.V.; Yakovleva, E.V., Thermochemistry of negatively charged ions. II. Energetics of formation of negative ions from acridanone and some of its derivatives, Rapid Commun. Mass Spectrom., 1999, 13, 10, 912-923, https://doi.org/10.1002/(SICI)1097-0231(19990530)13:10<912::AID-RCM585>3.0.CO;2-W . [all data]

Meot-ner, 1988
Meot-ner, M., Ionic Hydrogen Bond and Ion Solvation. ₆. Interaction Energies of the Acetate Ion with Organic Molecules. Comparison of CH₃COO^- with Cl^-, CN^-, and SH^-, J. Am. Chem. Soc., 1988, 110, 12, 3854, https://doi.org/10.1021/ja00220a022 . [all data]

Larson and McMahon, 1987
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. The energetics of interaction between cyanide ion and bronsted acids, J. Am. Chem. Soc., 1987, 109, 6230. [all data]

Payzant, Yamdagni, et al., 1971
Payzant, J.D.; Yamdagni, R.; Kebarle, P., Hydration of CN-, NO₂-, NO₃-, and HO- in the gas phase, Can. J. Chem., 1971, 49, 3308. [all data]

Larson and McMahon, 1983
Larson, J.W.; McMahon, T.B., Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements, J. Am. Chem. Soc., 1983, 105, 2944. [all data]

Arshadi, Yamdagni, et al., 1970
Arshadi, M.; Yamdagni, R.; Kebarle, P., Hydration of Halide Negative Ions in the Gas Phase. II. Comparison of Hydration Energies for the Alkali Positive and Halide Negative Ions, J. Phys. Chem., 1970, 74, 7, 1475, https://doi.org/10.1021/j100702a014 . [all data]

Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria, J. Am. Chem. Soc., 1984, 106, 517. [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]

Meot-ner, 1988, 2
Meot-ner, M., The Ionic Hydrogen Bond and Solvation. 7. Interaction Energies of Carbanions with Solvent Molecules, J. Am. Chem. Soc., 1988, 110, 12, 3858, https://doi.org/10.1021/ja00220a022 . [all data]

Hiraoka, Takimoto, et al., 1987
Hiraoka, K.; Takimoto, H.; Yamabe, S., Stabilities and Structures in Cluster Ions of Five-Membered Heterocyclic Compounds Containing O, N and S Atoms, J. Am. Chem. Soc., 1987, 109, 24, 7346, https://doi.org/10.1021/ja00258a018 . [all data]

Deakyne and Meot-Ner (Mautner), 1985
Deakyne, C.A.; Meot-Ner (Mautner), M., Unconventional Ionic Hydrogen Bonds. 2. NH+ pi. Complexes of Onium Ions with Olefins and Benzene Derivatives, J. Am. Chem. Soc., 1985, 107, 2, 474, https://doi.org/10.1021/ja00288a034 . [all data]

Meot-Ner (Mautner), 1988
Meot-Ner (Mautner), M., Models for Strong Interactions in Proteins and Enzymes. 2. Interactions of Ions with the Peptide Link and Imidazole, J. Am. Chem. Soc., 1988, 110, 10, 3075, https://doi.org/10.1021/ja00218a014 . [all data]

Gapeev and Yang, 2000
Gapeev, A.; Yang, C.-N., Binding Energies of Gas-Phase Ions with Pyrrole. Experimental and Quantum Chemical Results, J. Phys. Chem. A, 2000, 104, 14, 3246, https://doi.org/10.1021/jp992627d . [all data]

Huang and Rodgers, 2002
Huang, H.; Rodgers, M.T., Sigma versus Pi interactions in alkali metal ion binding to azoles: Threshold collision-induced dissociation and ab initio theory studies, J. Phys. Chem. A, 2002, 106, 16, 4277, https://doi.org/10.1021/jp013630b . [all data]

Zhuravleva, 2000
Zhuravleva, I.L., Evaluation of the polarity and boiling points of nitrogen-containing heterocyclic compounds by gas chromatography, Russ. Chem. Bull. (Engl. Transl.), 2000, 49, 2, 325-328, https://doi.org/10.1007/BF02494682 . [all data]

Golovnya, Kuz'menko, et al., 1999
Golovnya, R.V.; Kuz'menko, T.E.; Zhuravleva, I.L., Gas chromatographic indicator of the ability of five- and six-membered heterocyclic nitrogen-containing compounds for self-association in pure liquids, Russ. Chem. Bull. (Engl. Transl.), 1999, 48, 4, 726-729, https://doi.org/10.1007/BF02496256 . [all data]

Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L., Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases, Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]

Tibor and Anna, 1971
Tibor, T.; Anna, B., Gázkromatográfiás retenció és a kémiai szerkezet, I., Magy. Kem. Foly., 1971, 77, 576-587. [all data]

Kurbatova, Finkelstein, et al., 2004
Kurbatova, S.V.; Finkelstein, E.E.; Kolosova, E.A.; Kartashev, A.V.; Rashkin, S.V., Structural analogy method in studies of adamantanes, J. Struct. Chem., 2004, 45, 1, 144-150, https://doi.org/10.1023/B:JORY.0000041513.82837.4e . [all data]

Methven L., Tsoukka M., et al., 2007
Methven L.; Tsoukka M.; Oruna-Concha M.J.; Parker J.K.; Mottram D.S., Influence of sulfur amino acids on the volatile and nonvolatile components of cooked salmon (Salmo salar), J. Agric. Food Chem., 2007, 55, 4, 1427-1436, https://doi.org/10.1021/jf0625611 . [all data]

Solina, Baumgartner, et al., 2005
Solina, M.; Baumgartner, P.; Johnson, R.L.; Whitfield, F.B., Volatile aroma components of soy protein isolate and acid-hydrolysed vegetable protein, Food Chem., 2005, 90, 4, 861-873, https://doi.org/10.1016/j.foodchem.2004.06.005 . [all data]

Pino, Marbot, et al., 2004
Pino, J.A.; Marbot, R.; Vazquez, C., Volatile components of tamarind (Tamarindus indica L.) grown in Cuba, J. Essent. Oil Res., 2004, 16, 4, 318-320, https://doi.org/10.1080/10412905.2004.9698731 . [all data]

Pino, Marbot, et al., 2004, 2
Pino, J.A.; Marbot, R.; Rosado, A.; Vázquez, C., Volatile constituents of Malay rose apple [Syzygium malaccense (L.) Merr. Perry], Flavour Fragr. J., 2004, 19, 1, 32-35, https://doi.org/10.1002/ffj.1269 . [all data]

Bredie, Mottram, et al., 2002
Bredie, W.L.P.; Mottram, D.S.; Guy, R.C.E., Effect of temperature and pH on the generation of flavor volatiles in extrusion cooking of wheat flour, J. Agric. Food Chem., 2002, 50, 5, 1118-1125, https://doi.org/10.1021/jf0111662 . [all data]

Ames, Guy, et al., 2001
Ames, J.M.; Guy, R.C.E.; Kipping, G.J., Effect of pH and temperature on the formation of volatile compounds in cysteine/reducing sugar/starch mixtures during extrusion cooking, J. Agric. Food Chem., 2001, 49, 4, 1885-1894, https://doi.org/10.1021/jf0012547 . [all data]

Ames, Guy, et al., 2001, 2
Ames, J.M.; Guy, R.C.E.; Kipping, G.J., Effect of pH, temperature, and moisture on the formation of volatile compounds in glycine/glucose model systems, J. Agric. Food Chem., 2001, 49, 9, 4315-4323, https://doi.org/10.1021/jf010198m . [all data]

Kim, 2001
Kim, J.S., Einfluss der Temperatur beim Rösten von Sesam auf Aroma und antioxidative Eigenschaften des Öls, PhD Thesis, Technischen Universität Berlin zur Erlangung des akademischen Grades, Berlin, 2001, 151. [all data]

Izzo and Ho, 1991
Izzo, H.V.; Ho, C.-T., Isolation and identification of the volatile components of an extruded autolyzed yeast extract, J. Agric. Food Chem., 1991, 39, 12, 2245-2248, https://doi.org/10.1021/jf00012a029 . [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]

Zhang, Chien, et al., 1988
Zhang, Y.; Chien, M.; Ho.C.-T., Comparison of the volatile compounds obtained from thermal degradation of cysteine and glutathione in water, J. Agric. Food Chem., 1988, 36, 5, 992-996, https://doi.org/10.1021/jf00083a022 . [all data]

Elmore, Mottram, et al., 2000
Elmore, J.S.; Mottram, D.S.; Enser, M.; Wood, J.D., The effects of diet and breed on the volatile compounds of cooked lamb, Meat Sci., 2000, 55, 2, 149-159, https://doi.org/10.1016/S0309-1740(99)00137-0 . [all data]

Parker, Hassell, et al., 2000
Parker, J.K.; Hassell, G.M.E.; Mottram, D.S.; Guy, R.C.E., Sensory and instrumental analyses of volatiles generated during the extrusion cooking of oat flours, J. Agric. Food Chem., 2000, 48, 8, 3497-3506, https://doi.org/10.1021/jf991302r . [all data]

Lopez-Galilea I., Fournier N., et al., 2006
Lopez-Galilea I.; Fournier N.; Cid C.; Guichard E., Changes in headspace volatile concentrations of coffee brews caused by the roasting process and the brewing procedure, J. Agric. Food Chem., 2006, 54, 22, 8560-8566, https://doi.org/10.1021/jf061178t . [all data]

Mahadevan and Farmer, 2006
Mahadevan, K.; Farmer, L., Key Odor Impact Compounds in Three Yeast Extract Pastes, J. Agric. Food Chem., 2006, 54, 19, 7242-7250, https://doi.org/10.1021/jf061102x . [all data]

Chung, Yung, et al., 2002
Chung, H.-Y.; Yung, I.K.S.; Ma, W.C.J.; Kim, J.-S., Analysis of volatile components in frozen and dried scallops (Patinopecten yessoensis) by gas chromatography/mass spectrometry, Food Res. Int., 2002, 35, 1, 43-53, https://doi.org/10.1016/S0963-9969(01)00107-7 . [all data]

Chung, Yung, et al., 2001
Chung, H.Y.; Yung, I.K.S.; Kim, J.-S., Comparison of volatile components in dried scallops (Chlamys farreri and Patinopecten yessoensis) prepared by boiling and steaming methods, J. Agric. Food Chem., 2001, 49, 1, 192-202, https://doi.org/10.1021/jf000692a . [all data]

Chung, 2000
Chung, H.Y., Volatile flavor components in red fermented soybean (Glycine max) curds, J. Agric. Food Chem., 2000, 48, 5, 1803-1809, https://doi.org/10.1021/jf991272s . [all data]

Chung, 1999
Chung, H.Y., Volatile components in crabmeats of Charybdis feriatus, J. Agric. Food Chem., 1999, 47, 6, 2280-2287, https://doi.org/10.1021/jf981027t . [all data]

Ott, Fay, et al., 1997
Ott, A.; Fay, L.B.; Chaintreau, A., Determination and origin of the aroma impact compounds of yogurt flavor, J. Agric. Food Chem., 1997, 45, 3, 850-858, https://doi.org/10.1021/jf960508e . [all data]

Shimoda, Nakada, et al., 1997
Shimoda, M.; Nakada, Y.; Nakashima, M.; Osajima, Y., Quantitative comparison of volatile flavor compounds in deep-roasted and light-roasted sesame seed oil, J. Agric. Food Chem., 1997, 45, 8, 3193-3196, https://doi.org/10.1021/jf970172o . [all data]

Shimoda, Shiratsuchi, et al., 1996
Shimoda, M.; Shiratsuchi, H.; Nakada, Y.; Wu, Y.; Osajima, Y., Identification and sensory characterization of volatile flavor compounds in sesame seed oil, J. Agric. Food Chem., 1996, 44, 12, 3909-3912, https://doi.org/10.1021/jf960115f . [all data]

Shimoda, Shigematsu, et al., 1995
Shimoda, M.; Shigematsu, H.; Shiratsuchi, H.; Osajima, Y., Comparison of the odor concentrates by SDE and adsorptive column method from green tea infusion, J. Agric. Food Chem., 1995, 43, 6, 1616-1620, https://doi.org/10.1021/jf00054a037 . [all data]

Chung, Eiserich, et al., 1994
Chung, T.Y.; Eiserich, J.P.; Shibamoto, T., Volatile compounds produced from peanut oil heated with different amounts of cysteine, J. Agric. Food Chem., 1994, 42, 8, 1743-1746, https://doi.org/10.1021/jf00044a032 . [all data]

Shiratsuchi, Shimoda, et al., 1994
Shiratsuchi, H.; Shimoda, M.; Imayoshi, K.; Noda, K.; Osajima, Y., Off-flavor compounds in spray-dried skim milk powder, J. Agric. Food Chem., 1994, 42, 6, 1323-1327, https://doi.org/10.1021/jf00042a014 . [all data]

Shiratsuchi, Shimoda, et al., 1994, 2
Shiratsuchi, H.; Shimoda, M.; Imayoshi, K.; Noda, K.; Osajima, Y., Volatile flavor compounds in spray-dried skim milk powder, J. Agric. Food Chem., 1994, 42, 4, 984-988, https://doi.org/10.1021/jf00040a028 . [all data]

Chung and Cadwallader, 1993
Chung, H.Y.; Cadwallader, K.R., Volatile components in blue crab (Callinectes sapidus) meat and processing by-product, J. Food Sci., 1993, 58, 6, 1203-1207, https://doi.org/10.1111/j.1365-2621.1993.tb06148.x . [all data]

Matiella and Hsieh, 1990
Matiella, J.E.; Hsieh, T.C.-Y., Analysis of crabmeat volatile compounds, J. Food Sci., 1990, 55, 4, 962-966, https://doi.org/10.1111/j.1365-2621.1990.tb01575.x . [all data]

Tanchotikul and Hsieh, 1989
Tanchotikul, U.; Hsieh, T.C.-Y., Volatile Flavor Components in Crayfish Waste, J. Food Sci., 1989, 54, 6, 1515-1520, https://doi.org/10.1111/j.1365-2621.1989.tb05149.x . [all data]

Vejaphan, Hsieh, et al., 1988
Vejaphan, W.; Hsieh, T.C.Y.; Williams, S.S., Volatile flavor components from boiled crayfish (Procambarus clarkii) tail meat, J. Food Sci., 1988, 53, 6, 1666-1670, https://doi.org/10.1111/j.1365-2621.1988.tb07811.x . [all data]

Bianchi, Careri, et al., 2007
Bianchi, F.; Careri, M.; Mangia, A.; Musci, M., Retention indices in the analysis of food aroma volatile compounds in temperature-programmed gas chromatography: Database creation and evaluation of precision and robustness, J. Sep. Sci., 2007, 39, 4, 563-572, https://doi.org/10.1002/jssc.200600393 . [all data]

Alasalvar, Shahidi, et al., 2003
Alasalvar, C.; Shahidi, F.; Cadwallader, K.R., Comparison of natural and roasted Turkish Tombul hazelnut (Corylus avellana L.) volatiles and flavor by DHA/GC/MS and descriptive sensory analysis, J. Agric. Food Chem., 2003, 51, 17, 5067-5072, https://doi.org/10.1021/jf0300846 . [all data]

Baek and Cadwallader, 1996
Baek, H.H.; Cadwallader, K.R., Volatile compounds in flavor concentrates produced from crayfish-processing byproducts with and without protease treatment, J. Agric. Food Chem., 1996, 44, 10, 3262-3267, https://doi.org/10.1021/jf960023q . [all data]

Leffingwell and Alford, 2011
Leffingwell, J.; Alford, E.D., Volatile constituents of the giant pufball mushroom (Calvatia gigantea), Leffingwell Rep., 2011, 4, 1-17. [all data]

Piyachaiseth, Jirapakkul, et al., 2011
Piyachaiseth, T.; Jirapakkul, W.; Chaiseri, S., Aroma compounds of flash-fried rice, Kasetsart J. (Nat. Sci.), 2011, 45, 717-729. [all data]

Harrison and Priest, 2009
Harrison, B.M.; Priest, F.G., Composition of peaks used in the preparation of malt for Scotch Whisky production - influence of geographical source and extraction depth, J. Agric. Food Chem., 2009, 57, 6, 2385-2391, https://doi.org/10.1021/jf803556y . [all data]

Risticevic, Carasek, et al., 2008
Risticevic, S.; Carasek, E.; Pawliszyn, J., Headspace solid-phase microextraction-gas chromatographic-time-of-flight mass spectrometric methodology for geographical origin verification of coffee, Anal. Chim. Acta, 2008, 617, 1-2, 72-84, https://doi.org/10.1016/j.aca.2008.04.009 . [all data]

van Loon, Linssen, et al., 2005
van Loon, W.A.M.; Linssen, J.P.H.; Legger, A.; Posthumus, M.A.; Voragen, A.G.J., Identification and olfactometry of French fries flavour extracted at mouth conditions, Food Chem., 2005, 90, 3, 417-425, https://doi.org/10.1016/j.foodchem.2004.05.005 . [all data]

Sies A., Hirsch R., et al., 2002
Sies A.; Hirsch R.; Löscher R.; Tablack P.; Guth H., Direct thermal desorption and Fast-GC-TOF-MS for a rapid quality control of hazelnuts, 10th Weurman Flavour Research Symposium, 24 - 28 June 2002, Beaune, France, 2002. [all data]

Poligné, Collignan, et al., 2001
Poligné, I.; Collignan, A.; Trystram, G., Characterization of traditional processing of pork meat into boucané, Meat Sci., 2001, 59, 4, 377-389, https://doi.org/10.1016/S0309-1740(01)00090-0 . [all data]

Buttery, Ling, et al., 1997
Buttery, R.G.; Ling, L.C.; Stern, D.J., Studies on popcorn aroma and flavor volatiles, J. Agric. Food Chem., 1997, 45, 3, 837-843, https://doi.org/10.1021/jf9604807 . [all data]

Bellesia, Pinetti, et al., 1996
Bellesia, F.; Pinetti, A.; Bianchi, A.; Tirillini, B., Volatile compounds of the white truffle (Tuber magnaturn Pico) from middle Italy, Flavour Fragr. J., 1996, 11, 4, 239-243, https://doi.org/10.1002/(SICI)1099-1026(199607)11:4<239::AID-FFJ573>3.0.CO;2-A . [all data]

Buttery and Ling, 1995
Buttery, R.G.; Ling, L.C., Volatile flavor components of corn tortillas and related products, J. Agric. Food Chem., 1995, 43, 7, 1878-1882, https://doi.org/10.1021/jf00055a023 . [all data]

Macku and Shibamoto, 1991
Macku, C.; Shibamoto, T., Headspace volatile compounds formed from heated corn oil and corn oil with glycine, J. Agric. Food Chem., 1991, 39, 7, 1265-1269, https://doi.org/10.1021/jf00007a014 . [all data]

Macku and Shibamoto, 1991, 2
Macku, C.; Shibamoto, T., Volatile sulfur-containing compounds generated from the thermal interaction of corn oil and cysteine, J. Agric. Food Chem., 1991, 39, 11, 1987-1989, https://doi.org/10.1021/jf00011a021 . [all data]

del Rosario, de Lumen, et al., 1984
del Rosario, R.; de Lumen, B.O.; Habu, T.; Flath, R.A.; Mon, T.R.; Teranishi, R., Comparison of headspace volatiles from winged beans and soybeans, J. Agric. Food Chem., 1984, 32, 5, 1011-1015, https://doi.org/10.1021/jf00125a015 . [all data]

Liu, Xu, et al., 2007
Liu, Y.; Xu, X.-L.; Zhou, G.-H., Comparative study of volatile compounds in traditional Chinese Nanjing marinated duck by different extraction techniques, Int. J. Food Sci. Technol., 2007, 42, 5, 543-550, https://doi.org/10.1111/j.1365-2621.2006.01264.x . [all data]

Pino, Marbot, et al., 2005
Pino, J.A.; Marbot, R.; Rosado, A.; Vázquez, C., Volatile constituents of Malay rose apple [Syzygium malaccense (L.) Merr. Perry], Flavour Fragr. J., 2005, 20, 98-100. [all data]

Begnaud, Pérès, et al., 2003
Begnaud, F.; Pérès, C.; Berdagué, J.-L., Characterization of volatile effluents of livestock buildings by solid-phase microextraction, Int. J. Environ. Anal. Chem., 2003, 83, 10, 837-849, https://doi.org/10.1080/03067310310001603349 . [all data]

Machiels and Istasse, 2003
Machiels, D.; Istasse, L., Evaluation of two commercial solid-phase microextraction fibres for the analysis of target aroma compounds in cooked beef meat, Talanta, 2003, 61, 4, 529-537, https://doi.org/10.1016/S0039-9140(03)00319-9 . [all data]

Machiels, van Ruth, et al., 2003
Machiels, D.; van Ruth, S.M.; Posthumus, M.A.; Istasse, L., Gas chromatography-olfactometry analysis of the volatile compounds of two commercial Irish beef meats, Talanta, 2003, 60, 4, 755-764, https://doi.org/10.1016/S0039-9140(03)00133-4 . [all data]

Poligne, Collignan, et al., 2002
Poligne, I.; Collignan, A.; Trystram, G., Effects of salting, drying, cooking, and smoking operations on volatile compound formation and collor patterns in pork, Food Eng. Physical Properties, 2002, 67, 8, 2976-2986. [all data]

Luo and Agnew, 2001
Luo, J.; Agnew, M.P., Gas characteristics before and after biofiltration treating odorous emissions from animal rendering processes, Environ. Technol., 2001, 22, 9, 1091-1103, https://doi.org/10.1080/09593332208618220 . [all data]

Zenkevich, 1999
Zenkevich, I.G., Precalculation of Gas Chromatographic Retention Indices of Organic Compounds from Boiling Points of their Structural Analogues, Zh. Struct. Khim., 1999, 40, 1, 121-130. [all data]

Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technical_series₁997-01-01₁.pdf. [all data]

Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J., Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning, Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111 . [all data]

Kawai, Ishida, et al., 1991
Kawai, T.; Ishida, Y.; Kakiuchi, H.; Ikeda, N.; Higashida, T.; Nakamura, S., Flavor components of dried squid, J. Agric. Food Chem., 1991, 39, 4, 770-777, https://doi.org/10.1021/jf00004a031 . [all data]

Ramsey and Flanagan, 1982
Ramsey, J.D.; Flanagan, R.J., Detection and Identification of Volatile Organic Compounds in Blood by Headspace Gas Chromatography as an Aid to the Diagnosis of Solvent Abuse, J. Chromatogr., 1982, 240, 2, 423-444, https://doi.org/10.1016/S0021-9673(00)99622-5 . [all data]

Puvipirom and Chaisei, 2012
Puvipirom, J.; Chaisei, S., Contribution of roasted grains and seeds in aroma of oleang (Thai coffee drink), Int. Food Res. J., 2012, 19, 2, 583-588. [all data]

Budryn, Nebesny, et al., 2011
Budryn, G.; Nebesny, E.; Kula, J.; Majda, T.; Krysiak, W., HS-SPME/GC/MS Profiles of convectively and microwave roasted Ivory Coast Robusta coffee brews, Czech. J. Food Sci., 2011, 29, 2, 151-160. [all data]

Nebesny, Budryn, et al., 2007
Nebesny, E.; Budryn, G.; Kula, J.; Majda, T., The effect of roasting method on headspace composition of robusta coffee bean aroma, Eur. Food Res. Technol., 2007, 225, 1, 9-19, https://doi.org/10.1007/s00217-006-0375-0 . [all data]

Sanz, Maeztu, et al., 2002
Sanz, C.; Maeztu, L.; Zapelena, M.J.; Bello, J.; Cid, C., Profiles of volatile compounds and sensory analysis of three blends of coffee: influence of different proportions of Arabica and Robusta and influence of roasting coffee with sugar, J. Sci. Food Agric., 2002, 82, 8, 840-847, https://doi.org/10.1002/jsfa.1110 . [all data]

Maeztu, Sanz, et al., 2001
Maeztu, L.; Sanz, C.; Andueza, S.; de Peña, M.P.; Bello, J.; Cid, C., Characterization of espresso coffee aroma by static headspace GC-MS and sensory flavor profile, J. Agric. Food Chem., 2001, 49, 11, 5437-5444, https://doi.org/10.1021/jf0107959 . [all data]

Sanz, Ansorena, et al., 2001
Sanz, C.; Ansorena, D.; Bello, J.; Cid, C., Optimizing headspace temperature and time sampling for identification of volatile compounds in ground roasted Arabica coffee, J. Agric. Food Chem., 2001, 49, 3, 1364-1369, https://doi.org/10.1021/jf001100r . [all data]

Girard and Durance, 2000
Girard, B.; Durance, T., Headspace volatiles of sockeye and pink salmon as affected by retort process, Food Chem. Toxicol., 2000, 65, 1, 34-39. [all data]

Buttery, Orts, et al., 1999
Buttery, R.G.; Orts, W.J.; Takeoka, G.R.; Nam, Y., Volatile flavor components of rice cakes, J. Agric. Food Chem., 1999, 47, 10, 4353-4356, https://doi.org/10.1021/jf990140w . [all data]

Buttery and Ling, 1998
Buttery, R.G.; Ling, L.C., Additional studies on flavor components of corn tortilla chips, J. Agric. Food Chem., 1998, 46, 7, 2764-2769, https://doi.org/10.1021/jf980125b . [all data]

Kubota, Matsujage, et al., 1996
Kubota, K.; Matsujage, Y.; Sekiwa, Y.; Kobayashi, A., Identification of the characteristic volatile flavor compounds formed by cooking squid (Todarodes pacificus Steenstrup), Food Sci. Technol., 1996, 2, 3, 163-166. [all data]

Umano, Hagi, et al., 1995
Umano, K.; Hagi, Y.; Nakahara, K.; Shyoji, A.; Shibamoto, T., Volatile chemicals formed in the headspace of a heated D-glucose/L-cysteine Maillard model system, J. Agric. Food Chem., 1995, 43, 8, 2212-2218, https://doi.org/10.1021/jf00056a046 . [all data]

Hatsuko, Kazuko, et al., 1992
Hatsuko, S.; Kazuko, H.; Masayoshi, K.; Yoshiaki, I., Improvement of quality of likorine extract by heat treatment, J. Food Sci. Technol., 1992, 39, 11, 976-983, https://doi.org/10.3136/nskkk1962.39.976 . [all data]

Wong and Bernhard, 1988
Wong, J.M.; Bernhard, R.A., Effect of nitrogen source on pyrazine formation, J. Agric. Food Chem., 1988, 36, 1, 123-129, https://doi.org/10.1021/jf00079a032 . [all data]

Shibamoto and Russell, 1977
Shibamoto, T.; Russell, G.F., A study of the volatiles isolated from a D-glucose-hydrogen sulfide-ammonia model system, J. Agric. Food Chem., 1977, 25, 1, 109-112, https://doi.org/10.1021/jf60209a054 . [all data]

Welke, Manfroi, et al., 2012
Welke, J.E.; Manfroi, V.; Zanus, M.; Lazarotto, M.; Zini, C.A., Characterization of the volatile profile of Brazilian merlot wines through comprehensive two dimensional gas chromatography time-of-flight mass spectrometric detection, J. Chromatogr. A, 2012, 1226, 124-139, https://doi.org/10.1016/j.chroma.2012.01.002 . [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]

Kim. J.H., Ahn, et al., 2004
Kim. J.H.; Ahn, H.J.; Yook, H.S.; Kim, K.S.; Rhee, M.S.; Ryu, G.H.; Byun, M.W., Color, flavor, and sensory characteristics of gamma-irradiated salted and fermented anchovy sauce, Radiation Phys. Chem., 2004, 69, 2, 179-187, https://doi.org/10.1016/S0969-806X(03)00400-6 . [all data]

Finkelstein, Kurbatova, et al., 2002
Finkelstein, E.E.; Kurbatova, S.V.; Kolosova, E.A., Study of biological activity of structure analogies of adamantane, Proc. Samara State Univ., 2002, 26, 4, 121-128. [all data]

Muresan, Eillebrecht, et al., 2000
Muresan, S.; Eillebrecht, M.A.J.L.; de Rijk, T.C.; de Jonge, H.G.; Leguijt, T.; Nijhuis, H.H., Aroma profile development of intermediate chocolate products. I. Volatile constituents of block-milk, Food Chem., 2000, 68, 2, 167-174, https://doi.org/10.1016/S0308-8146(99)00171-5 . [all data]

Chang, Seitz, et al., 1995
Chang, C.-Y.; Seitz, L.M.; Chambers, E., IV, Volatile Flavor Components of Breads Made from Hard Red Winter Wheat and Hard White Winter Wheat, Cereal Chem., 1995, 72, 3, 237-242. [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]

Notes

Go To: Top, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  T	Temperature
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

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