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Bicyclo[2.2.1]heptan-2-one, 3,3-dimethyl-


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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

3,3-Dimethyl-2-norbornanone dimethyl ketal + Water = Bicyclo[2.2.1]heptan-2-one, 3,3-dimethyl- + 2Methyl Alcohol

By formula: C11H20O2 + H2O = C9H14O + 2CH4O

Quantity Value Units Method Reference Comment
Deltar5.36 ± 0.26kJ/molCmWiberg and Cunningham, 1990liquid phase; Heat of hydrolysis

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

View reactions leading to C9H14O+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
8.6PEFrost, Westwood, et al., 1980LLK
8.89PEFrost, Westwood, et al., 1980Vertical value; LLK

IR 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: Coblentz Society, Inc.

Condensed Phase Spectrum

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IR spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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Owner Copyright (C) 1987 by the Coblentz Society
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin WESTERN REGIONAL RES. USDA
Source reference COBLENTZ NO. 7290
Date 1967/05/15
State SOLUTION (10% CCl4 FOR 4000-1300, 10% CS2 FOR 1300-480 CM-1) VS SOLVENT
Instrument CARY 90 (GRATING)
Instrument parameters GRATING CHANGES: 3000, 2000, 1200 CM-1
Path length 0.010 CM, AND 0.010 CM
Resolution 2
Sampling procedure TRANSMISSION
Data processing DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY

This IR spectrum is from the Coblentz Society's evaluated infrared reference spectra collection.


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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Mass spectrum
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Additional Data

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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 Chemical Concepts
NIST MS number 190607

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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, temperature ramp

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Column type Active phase I Reference Comment
CapillaryDB-51083.Adams, 200030. m/0.26 mm/0.25 «mu»m, He, 3. K/min; Tstart: 60. C; Tend: 246. C
CapillaryMethyl Silicone1085.Adegoke, Rao, et al., 199830. m/0.32 mm/0.25 «mu»m, He, 60. C @ 2. min, 2. K/min, 250. C @ 5. min

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

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Column type Active phase I Reference Comment
CapillaryDB-51082.Yu, Liao, et al., 200730. m/0.25 mm/0.25 «mu»m, He, 3. K/min, 250. C @ 10. min; Tstart: 50. C
CapillaryRTX-11059.Cozzani, Muselli, et al., 200560. m/0.22 mm/0.25 «mu»m, 2. K/min, 220. C @ 20. min; Tstart: 60. C

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

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Column type Active phase I Reference Comment
CapillaryRTX-Wax1456.Cozzani, Muselli, et al., 200560. m/0.22 mm/0.25 «mu»m, 2. K/min, 220. C @ 20. min; Tstart: 60. C

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryHP-5 MS1086.Zouari, Ayadi, et al., 201230. m/0.25 mm/0.25 «mu»m, Helium, 50. C @ 1. min, 7. K/min, 250. C @ 5. min
CapillaryHP-51070.Bertoli, Lepnardi, et al., 201130. m/0.25 mm/0.25 «mu»m, Helium, 3. K/min; Tstart: 60. C; Tend: 240. C
CapillaryDB-51082.Scrivanti, Anton, et al., 200930. m/0.25 mm/0.25 «mu»m, Nitrogen, 2. K/min; Tstart: 40. C; Tend: 230. C
CapillaryHP-5 MS1082.Vagionas, Graikou, et al., 200730. m/0.25 mm/0.25 «mu»m, Helium, 3. K/min; Tstart: 60. C; Tend: 280. C
CapillaryZB-51083.Jürgens and Dötterl, 200460. m/0.25 mm/0.25 «mu»m, He, 40. C @ 4.6 min, 6. K/min, 260. C @ 1. min

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

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Column type Active phase I Reference Comment
CapillaryDB-11036.Albano, Lima, et al., 201230. m/0.25 mm/0.25 «mu»m, Hydrogen; Program: 45 0C 3 0C/min -> 175 0C 15 0C/min -> 300 0C (10 min)
CapillarySLB-5 MS1084.Costa, De Fina, et al., 200830. m/0.25 mm/0.25 «mu»m, Helium; Program: 50 0C 3 0C/min -> 250 0C (1 min) 10 0C/min -> 300 0C (5 min)
CapillarySLB-5 MS1078.Costa, De Fina, et al., 200830. m/0.25 mm/0.25 «mu»m, Helium; Program: not specified
CapillaryDB-51083.Isidorov, Zenkevich, et al., 1997Program: not specified

Normal alkane RI, polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryHP-Innowax1474.Demirci, Demirci, et al., 200560. m/0.25 mm/0.25 «mu»m, N2; Program: 60C(10min) => 4C/min => 220C (10min) => 1C/min => 240C
CapillaryHP-Innowax1474.Tabanca, Kirimer, et al., 200160. m/0.25 mm/0.25 «mu»m, He; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
CapillaryInnowax1474.Baser, Kürkcüoglu, et al., 199860. m/0.25 mm/0.25 «mu»m; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, Notes

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

Wiberg and Cunningham, 1990
Wiberg, K.B.; Cunningham, W.C., Jr., Thermochemical studies of carbonyl reactions. 4. Enthalpies of hydrolysis of norbornyl ketals, J. Org. Chem., 1990, 55, 679-684. [all data]

Frost, Westwood, et al., 1980
Frost, D.C.; Westwood, N.P.C.; Werstiuk, N.H., Ultraviolet photoelectron spectra of 2-norbornanone, 2,5-norbornanedione. Their akyl derivatives and thio-analogues. An investigation of transannular interactions by photoelectron spectroscopy, Can. J. Chem., 1980, 58, 1659. [all data]

Adams, 2000
Adams, R.P., The serrate leaf margined Juniperus (Section Sabina) of the western hemisphere: systematics and evolution based on leaf essential oils and Random Amplified Polymorphic DNAs (RAPDs), Biochem. Syst. Ecol., 2000, 28, 10, 975-989, https://doi.org/10.1016/S0305-1978(00)00022-3 . [all data]

Adegoke, Rao, et al., 1998
Adegoke, G.O.; Rao, L.J.M.; Shankaracharya, N.B., A comparison of the essential oils of Aframomum daniellii (Hook. f.) K. Schum. and Amomum subulatum Roxb, Flavour Fragr. J., 1998, 13, 5, 349-352, https://doi.org/10.1002/(SICI)1099-1026(1998090)13:5<349::AID-FFJ758>3.0.CO;2-O . [all data]

Yu, Liao, et al., 2007
Yu, J.Q.; Liao, Z.X.; Cai, X.Q.; Lei, J.C.; Zou, G.L., Composition, antimicrobial activity and cytotoxicity of essential oils from Aristolochia mollissima, Environmental Toxicology and Pharmacology, 2007, 23, 2, 162-167, https://doi.org/10.1016/j.etap.2006.08.004 . [all data]

Cozzani, Muselli, et al., 2005
Cozzani, S.; Muselli, A.; Desjobert, J.-M.; Bernardini, A.-F.; Tomi, F.; Casanova, J., Chemical composition of essential oil of Teucrium polium subsp. capitatum (L.) from Corsica, Flavour Fragr. J., 2005, 20, 4, 436-441, https://doi.org/10.1002/ffj.1463 . [all data]

Zouari, Ayadi, et al., 2012
Zouari, N.; Ayadi, I.; Fakhfakh, N.; Rebai, A.; Zouari, S., Variations of chemical composition of essential oils in wild-populations of Thymus algeriensis Boiss et Reut., a North African endemic species, Lipids in Health and Desease, 2012, 11, 1, 28-39, https://doi.org/10.1186/1476-511X-11-28 . [all data]

Bertoli, Lepnardi, et al., 2011
Bertoli, A.; Lepnardi, M.; Krzyzanowska, J.; Oleszek, W.; Pistelli, L., Mentha longifolia in vitro cultures as safe source of flavouring ingradients, Acta Biochem. Polonica, 2011, 58, 4, 581-587. [all data]

Scrivanti, Anton, et al., 2009
Scrivanti, L.R.; Anton, A.M.; Zygadlo, J.A., Essential oil conposition of Bothriochloa Kuntze (Poaceae) from South America and their chemotaxonomy, Biochem. Systematics Ecol., 2009, 37, 3, 206-213, https://doi.org/10.1016/j.bse.2009.03.009 . [all data]

Vagionas, Graikou, et al., 2007
Vagionas, K.; Graikou, K.; Ngassapa, O.; Runyoro, D.; Chinou, I., Composition and antimicrobial activity of the essential oils of three Satureja species growing in Tansania, Food Chem., 2007, 103, 2, 319-324, https://doi.org/10.1016/j.foodchem.2006.07.051 . [all data]

Jürgens and Dötterl, 2004
Jürgens, A.; Dötterl, S., Chemical composition of anther volatiles in Ranunculaceae: genera-specific profiles in Aemone, Aquilegia, Caltha, Pulsatilla, Ranunculus, and Trollius species, American Journal of Botany, 2004, 91, 12, 1969-1980, https://doi.org/10.3732/ajb.91.12.1969 . [all data]

Albano, Lima, et al., 2012
Albano, S.M.; Lima, A.S.; Miguel, M.G.; Pedro, L.G.; Barroso, J.G.; Figueiredo, A.C., Antioxidant, anti-5-lipoxygenase and antiacetylcholinesterase activities of essential oils and decoction water of some aromatic plants, Rec. Nat. Prod., 2012, 6, 1, 35-48. [all data]

Costa, De Fina, et al., 2008
Costa, R.; De Fina, M.R.; Valentino, M.R.; Rustaiyan, A.; Dugo, P.; Dugo, G.; Mondello, L., An investigation on the volatile composition of some Artemisia species from Iran, Flavour Fragr. J., 2008, 24, 2, 75-82, https://doi.org/10.1002/ffj.1919 . [all data]

Isidorov, Zenkevich, et al., 1997
Isidorov, V.; Zenkevich, I.; Sacharevich, T., Calculation of Gas Chromatographic Retention Indices for Monoterpenes and Terpenoids from Their Physico-Chemical Constants, Chem. Anal. (Warsaw), 1997, 42, 627-634. [all data]

Demirci, Demirci, et al., 2005
Demirci, B.; Demirci, F.; Baser, K.H.C., Headspace-SPME and hydrodistillation of two fragrant Artemisia sp., Flavour Fragr. J., 2005, 20, 4, 395-398, https://doi.org/10.1002/ffj.1426 . [all data]

Tabanca, Kirimer, et al., 2001
Tabanca, N.; Kirimer, N.; Demirci, B.; Demirci, F.; Can Baser, K.H., Composition and antimicrobial activity of the essential oils of Micromeria cristata subsp. phrygia and the enantiomeric distribution of borneol, J. Agric. Food Chem., 2001, 49, 9, 4300-4303, https://doi.org/10.1021/jf0105034 . [all data]

Baser, Kürkcüoglu, et al., 1998
Baser, K.H.C.; Kürkcüoglu, M.; Aytac, Z., Composition of the essential oil of Salvia euphratica Montbret ex Bentham var. euphratica from Turkey, Flavour Fragr. J., 1998, 13, 1, 63-64, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<63::AID-FFJ694>3.0.CO;2-Z . [all data]


Notes

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