1H-Pyrrole, 2-methyl-

Formula: C₅H₇N
Molecular weight: 81.1158
IUPAC Standard InChI: InChI=1S/C5H7N/c1-5-3-2-4-6-5/h2-4,6H,1H3
IUPAC Standard InChIKey: TVCXVUHHCUYLGX-UHFFFAOYSA-N
CAS Registry Number: 636-41-9
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: Pyrrole, 2-methyl-; α-Methylpyrrole; 2-Methylpyrrole; 2-methyl-1H-pyrrole
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Information on this page:
Other data available:
- Phase change data
- Mass spectrum (electron ionization)
Data at other public NIST sites:
- Gas Phase Kinetics Database
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Gas phase ion energetics data

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Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.01 ± 0.05	EI	Linda, Marino, et al., 1971	LLK
7.78 ± 0.01	PI	Potapov and Yuzhakova, 1970	RDSH

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₅H₆N⁺	10.3 ± 0.1	H	PI	Potapov and Yuzhakova, 1970	RDSH

Gas Chromatography

Go To: Top, Gas phase ion energetics data, References, Notes

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

Kovats' RI, polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	PEG-2000	152.	1562.	Anderson, Jurel, et al., 1973	He, Celite 545 (44-60 mesh); Column length: 3. m
Packed	PEG-2000	179.	1575.	Anderson, Jurel, et al., 1973	He, Celite 545 (44-60 mesh); Column length: 3. m
Packed	PEG-2000	200.	1590.	Anderson, Jurel, et al., 1973	He, Celite 545 (44-60 mesh); Column length: 3. m

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

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5	853.	Solina, Baumgartner, et al., 2005	25. m/0.2 mm/1. μm, He, 5. K/min, 280. C @ 5. min; T_start: 40. C
Capillary	BPX-5	866.	Bredie, Mottram, et al., 2002	50. m/0.32 mm/0.5 μm, 60. C @ 5. min, 4. K/min, 250. C @ 20. min
Capillary	BPX-5	850.	Ames, Guy, et al., 2001	50. m/0.32 mm/0.5 μm, He, 60. C @ 5. min, 4. K/min, 250. C @ 10. min
Capillary	BPX-5	850.	Ames, Guy, et al., 2001	50. m/0.32 mm/0.5 μm, He, 60. C @ 5. min, 4. K/min, 250. C @ 10. min
Capillary	DB-1	813.	Kim, 2001	60. m/0.32 mm/1. μm, He, 40. C @ 5. min, 2. K/min; T_end: 220. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	CP Sil 8 CB	847.	Oruna-Concha, Bakker, et al., 2002	60. m/0.25 mm/0.25 μm, He; Program: 0C => rapidly => 40C(8min) => 4C/min => 250C(10min)
Capillary	DB-5	856.	Parker, Hassell, et al., 2000	50. m/0.32 mm/0.5 μm, He; Program: oC(5min) => 60C/min => 60C (5min) => 4C/min => 250C
Capillary	BPX-5	855.	Bredie, Mottram, et al., 1998	50. m/0.32 mm/0.5 μm, He; Program: OC (5min) => 60C/min => 60C(5min) => 4C/min => 250C

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

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Column type	Active phase	I	Reference	Comment
Capillary	CP-Wax 52CB	1566.	Mahadevan and Farmer, 2006	60. C @ 5. min, 4. K/min, 220. C @ 30. min; Column length: 50. m; Column diameter: 0.32 mm
Capillary	CP-Wax 52CB	1549.	Mahadevan and Farmer, 2006	60. C @ 5. min, 4. K/min, 220. C @ 30. min; Column length: 50. m; Column diameter: 0.32 mm
Capillary	Supelcowax-10	1557.	Elmore, Nisyrios, et al., 2005	60. m/0.25 mm/0.25 μm, He, 40. C @ 2. min, 4. K/min; T_end: 280. C
Capillary	DB-Wax	1551.	Kim, 2001	60. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 200. C @ 30. min
Capillary	Supelcowax-10	1563.	Chung, 2000	60. m/0.25 mm/0.25 μm, He, 2. K/min, 195. C @ 90. min; T_start: 35. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	CP-Wax 52CB	1570.	Alasalvar, Shahidi, et al., 2003	60. m/0.25 mm/0.25 μm, He; Program: 40C => 5C/min => 60C => 2.5C/min => 155C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	MDN-5	843.	van Loon, Linssen, et al., 2005	60. m/0.25 mm/0.25 μm, He, 40. C @ 4. min, 4. K/min, 270. C @ 5. min
Capillary	MDN-5	845.	van Loon, Linssen, et al., 2005	60. m/0.25 mm/0.25 μm, He, 40. C @ 4. min, 4. K/min, 270. C @ 5. min
Capillary	SPB-5	839.	Sebastian, Viallon-Fernandez, et al., 2003	60. m/0.32 mm/1.0 μm, Helium, 3. K/min; T_start: 30. C; T_end: 230. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	Methyl Silicone	837.	Zenkevich, 1999	Program: not specified
Capillary	DB-1	812.	Kawai, Ishida, et al., 1991	60. m/0.25 mm/0.25 μm; Program: not specified
Capillary	DB-1	812.	Kawai, Ishida, et al., 1991	60. m/0.25 mm/0.25 μm; Program: not specified

Normal alkane RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-Innowax	1537.	Puvipirom and Chaisei, 2012	15. m/0.32 mm/0.50 μm, Helium, 3. K/min; T_start: 40. C; T_end: 250. C
Capillary	HP-Wax	1580.	Sanz, Maeztu, et al., 2002	60. m/0.25 mm/0.5 μm, He, 40. C @ 6. min, 3. K/min; T_end: 190. C

References

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

Linda, Marino, et al., 1971
Linda, P.; Marino, G.; Pignataro, S., A comparison of sensitivities to substituent effects of five- membered heteroaromatic rings in gas phase ionization, J. Chem. Soc. B, 1971, 1585. [all data]

Potapov and Yuzhakova, 1970
Potapov, V.K.; Yuzhakova, O.A., Photoionization and electronic structure of pyrrole and its methyl derivatives, Dokl. Akad. Nauk SSSR, 1970, 192, 131, In original 365. [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]

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]

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]

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]

Oruna-Concha, Bakker, et al., 2002
Oruna-Concha, M.J.; Bakker, J.; Ames, J.M., Comparison of the volatile components of two cultivars of potato cooked by boiling, conventional baking and microwave baking, J. Sci. Food Agric., 2002, 82, 9, 1080-1087, https://doi.org/10.1002/jsfa.1148 . [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]

Bredie, Mottram, et al., 1998
Bredie, W.L.P.; Mottram, D.S.; Guy, R.C.E., Aroma volatiles generated during extrusion cooking of maize flour, J. Agric. Food Chem., 1998, 46, 4, 1479-1487, https://doi.org/10.1021/jf9708857 . [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]

Elmore, Nisyrios, et al., 2005
Elmore, J.S.; Nisyrios, I.; Mottram, D.S., Analysis of the headspace aroma compounds of walnuts (Juglans regia L.), Flavour Fragr. J., 2005, 20, 5, 501-506, https://doi.org/10.1002/ffj.1477 . [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]

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]

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]

Sebastian, Viallon-Fernandez, et al., 2003
Sebastian, I.; Viallon-Fernandez, C.; Berge, P.; Berdague, J.-L., Analysis of the volatile fraction of lamb fat tissue: influence of the type of feeding, Sciences des Aliments, 2003, 23, 4, 497-511, https://doi.org/10.3166/sda.23.497-511 . [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]

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]

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]

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]

Notes

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

Symbols used in this document:

AE Appearance energy
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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