1-Propanol, 2,2-dimethyl-

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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
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil385. ± 3.KAVGN/AAverage of 26 out of 27 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus327.KN/ARai, Singh, et al., 1987Uncertainty assigned by TRC = 0.2 K; TRC
Tfus325.7KN/AMurrill and Breed, 1970Crystal phase 1 phase; Uncertainty assigned by TRC = 3. K; TRC
Tfus324.45KN/AMcKenna, Tartar, et al., 1953Uncertainty assigned by TRC = 0.4 K; TRC
Tfus323.15KN/AWhitmore, 1938Uncertainty assigned by TRC = 1.5 K; TRC
Quantity Value Units Method Reference Comment
Δvap12.4 ± 0.07kcal/molGS,BKulikov, Verevkin, et al., 2001Based on data from 274. to 312. K.; AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
11.4345.AStephenson and Malanowski, 1987Based on data from 330. to 387. K.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
0.69328.2ACStraka, van Genderen, et al., 2007Based on data from 10. to 370. K.; AC
0.925329.8N/ACenský, Ruzicka, et al., 2003AC
0.891329.8N/ASalud, López, et al., 1999AC
0.84328.1DSCGranzow, 1996AC
0.970325.N/AMurrill and Breed, 1970, 2AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
3.210146.Parks, Huffman, et al., 1933CAL
0.19213.
4.034264.

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
1.067242.crystaline, IIcrystaline, IMurrill and Breed, 1970, 2DH
0.9696325.crystaline, IliquidMurrill and Breed, 1970, 2DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
4.40242.crystaline, IIcrystaline, IMurrill and Breed, 1970, 2DH
2.99325.crystaline, IliquidMurrill and Breed, 1970, 2DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

C5H11O- + Hydrogen cation = 1-Propanol, 2,2-dimethyl-

By formula: C5H11O- + H+ = C5H12O

Quantity Value Units Method Reference Comment
Δr372.6 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr373.1 ± 2.3kcal/molD-EAJanousek, Zimmerman, et al., 1978gas phase; B
Δr372.7 ± 2.0kcal/molCIDCHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B
Quantity Value Units Method Reference Comment
Δr366.0 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr366.5 ± 2.4kcal/molH-TSJanousek, Zimmerman, et al., 1978gas phase; B
Δr366.1 ± 2.1kcal/molH-TSHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B

C8H5- + 1-Propanol, 2,2-dimethyl- = (C8H5- • 1-Propanol, 2,2-dimethyl-)

By formula: C8H5- + C5H12O = (C8H5- • C5H12O)

Quantity Value Units Method Reference Comment
Δr24.2 ± 2.9kcal/molN/ACaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M
Quantity Value Units Method Reference Comment
Δr29.3cal/mol*KN/ACaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Δr15.5 ± 2.0kcal/molIMRECaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M

C6H13O- + 1-Propanol, 2,2-dimethyl- = (C6H13O- • 1-Propanol, 2,2-dimethyl-)

By formula: C6H13O- + C5H12O = (C6H13O- • C5H12O)

Quantity Value Units Method Reference Comment
Δr28.5kcal/molICRCaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Δr29.3cal/mol*KN/ACaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Δr19.8kcal/molICRCaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M

C5H11O- + 1-Propanol, 2,2-dimethyl- = (C5H11O- • 1-Propanol, 2,2-dimethyl-)

By formula: C5H11O- + C5H12O = (C5H11O- • C5H12O)

Quantity Value Units Method Reference Comment
Δr29.0 ± 2.9kcal/molN/ACaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr19.9 ± 2.0kcal/molIMRECaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B

C6H13O- + 1-Propanol, 2,2-dimethyl- = (C6H13O- • 1-Propanol, 2,2-dimethyl-)

By formula: C6H13O- + C5H12O = (C6H13O- • C5H12O)

Quantity Value Units Method Reference Comment
Δr28.4 ± 2.9kcal/molN/ACaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr19.7 ± 2.0kcal/molIMRECaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B

Gas phase ion energetics data

Go To: Top, Phase change data, Reaction thermochemistry data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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
LL - Sharon G. Lias and Joel F. Liebman

View reactions leading to C5H12O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)190.1kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity182.9kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.72 ± 0.05EIBissonnette, George, et al., 1990LL

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C4H8+10.2 ± 0.1CH3OHEIBissonnette, George, et al., 1990LL

De-protonation reactions

C5H11O- + Hydrogen cation = 1-Propanol, 2,2-dimethyl-

By formula: C5H11O- + H+ = C5H12O

Quantity Value Units Method Reference Comment
Δr372.6 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr373.1 ± 2.3kcal/molD-EAJanousek, Zimmerman, et al., 1978gas phase; B
Δr372.7 ± 2.0kcal/molCIDCHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B
Quantity Value Units Method Reference Comment
Δr366.0 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr366.5 ± 2.4kcal/molH-TSJanousek, Zimmerman, et al., 1978gas phase; B
Δr366.1 ± 2.1kcal/molH-TSHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B

Ion clustering data

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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

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

C5H11O- + 1-Propanol, 2,2-dimethyl- = (C5H11O- • 1-Propanol, 2,2-dimethyl-)

By formula: C5H11O- + C5H12O = (C5H11O- • C5H12O)

Quantity Value Units Method Reference Comment
Δr29.0 ± 2.9kcal/molN/ACaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr19.9 ± 2.0kcal/molIMRECaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B

C6H13O- + 1-Propanol, 2,2-dimethyl- = (C6H13O- • 1-Propanol, 2,2-dimethyl-)

By formula: C6H13O- + C5H12O = (C6H13O- • C5H12O)

Quantity Value Units Method Reference Comment
Δr28.4 ± 2.9kcal/molN/ACaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr19.7 ± 2.0kcal/molIMRECaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B

C6H13O- + 1-Propanol, 2,2-dimethyl- = (C6H13O- • 1-Propanol, 2,2-dimethyl-)

By formula: C6H13O- + C5H12O = (C6H13O- • C5H12O)

Quantity Value Units Method Reference Comment
Δr28.5kcal/molICRCaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Δr29.3cal/mol*KN/ACaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Δr19.8kcal/molICRCaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M

C8H5- + 1-Propanol, 2,2-dimethyl- = (C8H5- • 1-Propanol, 2,2-dimethyl-)

By formula: C8H5- + C5H12O = (C8H5- • C5H12O)

Quantity Value Units Method Reference Comment
Δr24.2 ± 2.9kcal/molN/ACaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M
Quantity Value Units Method Reference Comment
Δr29.3cal/mol*KN/ACaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Δr15.5 ± 2.0kcal/molIMRECaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M

IR Spectrum

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References, Notes

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

View scan of original (hardcopy) spectrum.

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

Owner COPYRIGHT (C) 1988 by COBLENTZ SOCIETY INC.
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin DOW CHEMICAL COMPANY
Source reference COBLENTZ NO. 7960
Date 1964/04/03
Name(s) Neopentyl alcohol
State SOLUTION (10% CCl4 FOR 3800-1340, 10% CS2 FOR 1340-450 CM-1)
Instrument DOW KBr FOREPRISM-GRATING
Instrument parameters BLAZED AT 3.5, 12.0, 20.0 MICRON AND CHANGED AT 5.0, 7.5, 14.9 MICRON
Path length 0.011 CM, 0.011 CM
SPECTRAL CONTAMINATION DUE TO CS2 AROUND 850 AND CCl4 AROUND 1550 CM-1 HAVE BEEN SUBTRACTED
Resolution 2
Sampling procedure TRANSMISSION
Data processing DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY

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


Mass spectrum (electron ionization)

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, References, Notes

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

View image of digitized spectrum (can be printed in landscape orientation).

Due to licensing restrictions, this spectrum cannot be downloaded.

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.
NIST MS number 19479

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.


References

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Notes

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

Rai, Singh, et al., 1987
Rai, U.S.; Singh, O.P.; Singh, N.B., Solidification behavior of organic eutectic, succinonitrile-neopenty alcohol system, J. Chim. Phys. Phys.-Chim. Biol., 1987, 84, 483. [all data]

Murrill and Breed, 1970
Murrill, E.; Breed, L.W., Solid-solid phase transitions determined by differential scanning calorime- try. Part I. Tetrahedral Substances., Thermochim. Acta, 1970, 1, 239. [all data]

McKenna, Tartar, et al., 1953
McKenna, F.E.; Tartar, H.V.; Lingafelter, E.C., Studies of hemiacetal formation in alcohol - aldehyde systems: II refraction studies, J. Am. Chem. Soc., 1953, 75, 604-7. [all data]

Whitmore, 1938
Whitmore, F.C., The Reducing Action of Grignard Reagents on Acyl Chlorides, Recl. Trav. Chim. Pays-Bas, 1938, 57, 562. [all data]

Kulikov, Verevkin, et al., 2001
Kulikov, Dmitry; Verevkin, Sergey P.; Heintz, Andreas, Determination of Vapor Pressures and Vaporization Enthalpies of the Aliphatic Branched C 5 and C 6 Alcohols, J. Chem. Eng. Data, 2001, 46, 6, 1593-1600, https://doi.org/10.1021/je010187p . [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]

Straka, van Genderen, et al., 2007
Straka, Martin; van Genderen, Aad; Ruzicka, Kvetoslav; Ruzicka, Vlastimil, Heat Capacities in the Solid and in the Liquid Phase of Isomeric Pentanols, J. Chem. Eng. Data, 2007, 52, 3, 794-802, https://doi.org/10.1021/je060411g . [all data]

Censký, Ruzicka, et al., 2003
Censký, Miroslav; Ruzicka, Kvetoslav; Ruzicka, Vlastimil; Zábranský, Milan, Heat capacities of alkanols, Thermochimica Acta, 2003, 408, 1-2, 45-53, https://doi.org/10.1016/S0040-6031(03)00317-4 . [all data]

Salud, López, et al., 1999
Salud, Josep; López, David O.; Barrio, Maria; Tamarit, Josep Ll., Two-component systems of isomorphous orientationally disordered crystals. Part 1 Packing of the mixed crystals, J. Mater. Chem., 1999, 9, 4, 909-916, https://doi.org/10.1039/a808258h . [all data]

Granzow, 1996
Granzow, Bettina, Hydrogen bonding and phase transitions of a group of alcohols derived from 2,2-dimethylpropane, Journal of Molecular Structure, 1996, 381, 1-3, 127-131, https://doi.org/10.1016/0022-2860(96)09232-0 . [all data]

Murrill and Breed, 1970, 2
Murrill, E.; Breed, L., Solid-solid phase transitions determined by differential scanning calorimetry, Thermochim. Acta, 1970, 1, 239-246. [all data]

Parks, Huffman, et al., 1933
Parks, G.S.; Huffman, H.M.; Barmore, M., Thermal Data on Organic Compounds. XI. The Heat Capacities, Entropies and Free Energies of Ten Compounds Containing Oxygen or Nitrogen, J. Am. Chem. Soc., 1933, 55, 7, 2733, https://doi.org/10.1021/ja01334a016 . [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]

Janousek, Zimmerman, et al., 1978
Janousek, B.K.; Zimmerman, A.H.; Reed, K.J.; Brauman, J.I., Electron detachment from aliphatic molecular anions. Gas phase electron affinites of methoxyl, tert-butoxyl, and neopentoxyl radicals, J. Am. Chem. Soc., 1978, 100, 6142. [all data]

Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G., The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols, Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W . [all data]

Caldwell, Rozeboom, et al., 1984
Caldwell, G.; Rozeboom, M.D.; Kiplinger, J.P.; Bartmess, J.E., Anion-alcohol hydrogen bond strengths in the gas phase, J. Am. Chem. Soc., 1984, 106, 4660. [all data]

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Thermodynamics of the Association Reactions OH- - H2O = HOHOH- and CH3O- - CH3OH = CH3OHOCH3- in the Gas Phase, J. Phys. Chem., 1990, 94, 12, 5184, https://doi.org/10.1021/j100375a076 . [all data]

Meot-ner and Sieck, 1986
Meot-ner, M.; Sieck, L.W., Relative acidities of water and methanol, and the stabilities of the dimer adducts, J. Phys. Chem., 1986, 90, 6687. [all data]

Meot-Ner(Mautner), 1986
Meot-Ner(Mautner), M., Comparative Stabilities of Cationic and Anionic Hydrogen-Bonded Networks. Mixed Clusters of Water-Methanol, J. Am. Chem. Soc., 1986, 108, 20, 6189, https://doi.org/10.1021/ja00280a014 . [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]

Bissonnette, George, et al., 1990
Bissonnette, M.; George, M.; Holmes, J.L., The experimental investigation of [C5H12O] ion structures related to neopentyl alcohol and its methyl ether, Int. J. Mass Spectrom. Ion Processes, 1990, 101, 309. [all data]


Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), References