1-Butanol

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Gas phase thermochemistry data

Go To: Top, 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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Δfgas-277. ± 5.kJ/molAVGN/AAverage of 13 values; Individual data points
Quantity Value Units Method Reference Comment
gas361.98J/mol*KN/AChao J., 1986Other values of S(298.15 K) based on low-temperature thermal measurements are (in J/mol*K): 363.17 [65COU/HAL], 362.33 [ Chermin H.A.G., 1961], and 361.9 [ Buckley E., 1967].; GT

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
42.5450.Thermodynamics Research Center, 1997p=1 bar. Recommended S(T) and Cp(T) values agree with those calculated by [ Chermin H.A.G., 1961] within 1.5 J/mol*K. S(T) values calculated by [ Dyatkina M.E., 1954] are different from values given here by 12-30 J/mol*K. Please also see Chao J., 1986.; GT
58.33100.
70.10150.
81.28200.
100.68273.15
108.03 ± 0.25298.15
108.58300.
138.16400.
164.42500.
186.38600.
204.83700.
220.56800.
234.15900.
245.931000.
256.181100.
265.101200.
272.861300.
279.631400.
285.541500.
297.31750.
305.82000.
312.22250.
316.92500.
320.52750.
323.23000.

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
140.93 ± 0.79395.25Stromsoe E., 1970Ideal gas heat capacities are given by [ Stromsoe E., 1970] as a linear function Cp=f1*(a+bT). This expression approximates the experimental values with the average deviation of 0.79 J/mol*K. The accuracy of the experimental heat capacities [ Stromsoe E., 1970] is estimated as less than 0.3%.; GT
137.88398.15
143.00 ± 0.79404.15
144.16 ± 0.79409.15
142.06413.15
146.58 ± 0.79419.55
149.26 ± 0.79431.05
147.42433.15
151.60 ± 0.79441.15
152.66453.15
155.88 ± 0.79459.55
162.55 ± 0.79488.25
169.95 ± 0.79520.05
175.97 ± 0.79545.95
181.20 ± 0.79568.45
189.31 ± 0.79603.35

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Quantity Value Units Method Reference Comment
IE (evaluated)9.99 ± 0.05eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)789.2kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity758.9kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
10.10 ± 0.05EIHolmes and Lossing, 1991LL
9.99 ± 0.05PIPECOShao, Baer, et al., 1988LL
10.64 ± 0.07EIBowen and Maccoll, 1984LBLHLM
10.09 ± 0.02PECocksey, Eland, et al., 1971LLK
10.37PEBaker, Betteridge, et al., 1971LLK
10.37PEBaker, Betteridge, et al., 1971LLK
10.04PIWatanabe, Nakayama, et al., 1962RDSH
10.43PEBenoit and Harrison, 1977Vertical value; LLK
10.44 ± 0.03PEPeel and Willett, 1975Vertical value; LLK
10.37PEKatsumata, Iwai, et al., 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH3O+11.36 ± 0.06n-C3H7EISelim and Helal, 1981LLK
CH3O+11.46?EILambdin, Tuffly, et al., 1959RDSH
C2H2O+11.23?EILambdin, Tuffly, et al., 1959RDSH
C4H8+10.18 ± 0.05H2OPIPECOShao, Baer, et al., 1988LL
C4H8+10.20 ± 0.10H2OEIBowen and Maccoll, 1984LBLHLM

De-protonation reactions

C4H9O- + Hydrogen cation = 1-Butanol

By formula: C4H9O- + H+ = C4H10O

Quantity Value Units Method Reference Comment
Δr1570. ± 8.4kJ/molCIDCHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B
Δr1571. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr1569. ± 12.kJ/molG+TSBoand, Houriet, et al., 1983gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1543. ± 8.8kJ/molH-TSHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B
Δr1543. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr1541. ± 12.kJ/molCIDCBoand, Houriet, et al., 1983gas phase; value altered from reference due to change in acidity scale; B

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics 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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
RCD - Robert C. Dunbar

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

CH6N+ + 1-Butanol = (CH6N+ • 1-Butanol)

By formula: CH6N+ + C4H10O = (CH6N+ • C4H10O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity Value Units Method Reference Comment
Δr98.3kJ/molPHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr110.J/mol*KN/AMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
44.4495.PHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M

C3H9Si+ + 1-Butanol = (C3H9Si+ • 1-Butanol)

By formula: C3H9Si+ + C4H10O = (C3H9Si+ • C4H10O)

Quantity Value Units Method Reference Comment
Δr185.kJ/molPHPMSWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr130.J/mol*KN/AWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
124.468.PHPMSWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated; M

C3H9Sn+ + 1-Butanol = (C3H9Sn+ • 1-Butanol)

By formula: C3H9Sn+ + C4H10O = (C3H9Sn+ • C4H10O)

Quantity Value Units Method Reference Comment
Δr153.kJ/molPHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr136.J/mol*KN/AStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
81.6525.PHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

C4H11O+ + 1-Butanol = (C4H11O+ • 1-Butanol)

By formula: C4H11O+ + C4H10O = (C4H11O+ • C4H10O)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
Δr132.kJ/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984; M
Quantity Value Units Method Reference Comment
Δr129.J/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984; M
Quantity Value Units Method Reference Comment
Δr93.3kJ/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984; M

thiophenoxide anion + 1-Butanol = (thiophenoxide anion • 1-Butanol)

By formula: C6H5S- + C4H10O = (C6H5S- • C4H10O)

Quantity Value Units Method Reference Comment
Δr61.1kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr105.J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

Chlorine anion + 1-Butanol = (Chlorine anion • 1-Butanol)

By formula: Cl- + C4H10O = (Cl- • C4H10O)

Quantity Value Units Method Reference Comment
Δr73.6 ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Δr97.1J/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)CH3OH, Entropy change calculated or estimated; Larson and McMahon, 1984, 2; M
Quantity Value Units Method Reference Comment
Δr44.8 ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M

Fluorine anion + 1-Butanol = C4H9D10FO-

By formula: F- + C4H10O = C4H9D10FO-

Quantity Value Units Method Reference Comment
Δr101. ± 8.4kJ/molIMREWilkinson, Szulejko, et al., 1992gas phase; Reported relative to ROH..F-, 0.5 kcal/mol weaker.; B

Fluorine anion + 1-Butanol = (Fluorine anion • 1-Butanol)

By formula: F- + C4H10O = (F- • C4H10O)

Quantity Value Units Method Reference Comment
Δr135. ± 8.4kJ/molIMRELarson and McMahon, 1983gas phase; B,M
Quantity Value Units Method Reference Comment
Δr108.J/mol*KN/ALarson and McMahon, 1983gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M
Quantity Value Units Method Reference Comment
Δr103. ± 8.4kJ/molIMRELarson and McMahon, 1983gas phase; B,M

Lithium ion (1+) + 1-Butanol = (Lithium ion (1+) • 1-Butanol)

By formula: Li+ + C4H10O = (Li+ • C4H10O)

Quantity Value Units Method Reference Comment
Δr178. ± 7.9kJ/molCIDTRodgers and Armentrout, 2000RCD

Magnesium ion (1+) + 1-Butanol = (Magnesium ion (1+) • 1-Butanol)

By formula: Mg+ + C4H10O = (Mg+ • C4H10O)

Quantity Value Units Method Reference Comment
Δr270. ± 20.kJ/molICROperti, Tews, et al., 1988gas phase; switching reaction,Thermochemical ladder(Mg+)CH3OH; M

Sodium ion (1+) + 1-Butanol = (Sodium ion (1+) • 1-Butanol)

By formula: Na+ + C4H10O = (Na+ • C4H10O)

Quantity Value Units Method Reference Comment
Δr109. ± 5.0kJ/molCIDTRodgers and Armentrout, 1999RCD

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
82.4298.IMREMcMahon and Ohanessian, 2000Anchor alanine=39.89; RCD

Mass spectrum (electron ionization)

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

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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 NIST Mass Spectrometry Data Center, 1994
NIST MS number 133176

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References

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, 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.

Chao J., 1986
Chao J., Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties, J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]

Chermin H.A.G., 1961
Chermin H.A.G., Thermo data for petrochemicals. Part 28. Gaseous normal alcohols. The important thermo properties are presented for all the gaseous normal alcohols from methanol through n-decanol, Petrol. Refiner, 1961, 40 (4), 127-130. [all data]

Buckley E., 1967
Buckley E., Chemical equilibria. Part 2. Dehydrogenation of propanol and butanol, Trans. Faraday Soc., 1967, 63, 895-901. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Dyatkina M.E., 1954
Dyatkina M.E., Thermodynamic functions of normal alcohols (propanol, butanol, ethylene glycol), Zh. Fiz. Khim., 1954, 28, 377. [all data]

Stromsoe E., 1970
Stromsoe E., Heat capacity of alcohol vapors at atmospheric pressure, J. Chem. Eng. Data, 1970, 15, 286-290. [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]

Holmes and Lossing, 1991
Holmes, J.L.; Lossing, F.P., Ionization energies of homologous organic compounds and correlation with molecular size, Org. Mass Spectrom., 1991, 26, 537. [all data]

Shao, Baer, et al., 1988
Shao, J.D.; Baer, T.; Lewis, D.K., Dissociation dynamics of energy-selected ion-dipole complexes. 2. Butyl alcohol ions, J. Phys. Chem., 1988, 92, 5123. [all data]

Bowen and Maccoll, 1984
Bowen, R.D.; Maccoll, A., Low energy, low temperature mass spectra, Org. Mass Spectrom., 1984, 19, 379. [all data]

Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J., The effect of alkyl substitution on ionisation potential, J. Chem. Soc., 1971, (B), 790. [all data]

Baker, Betteridge, et al., 1971
Baker, A.D.; Betteridge, D.; Kemp, N.R.; Kirby, R.E., Application of photoelectron spectrometry to pesticide analysis. II.Photoelectron spectra of hydroxy-, and halo-alkanes and halohydrins, Anal. Chem., 1971, 43, 375. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G., Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules, J. Am. Chem. Soc., 1977, 99, 3980. [all data]

Peel and Willett, 1975
Peel, J.B.; Willett, G.D., Photoelectron spectroscopic studies of the higher alcohols, Aust. J. Chem., 1975, 28, 2357. [all data]

Katsumata, Iwai, et al., 1973
Katsumata, S.; Iwai, T.; Kimura, K., Photoelectron spectra and sum rule consideration. Higher alkyl amines and alcohols, Bull. Chem. Soc. Jpn., 1973, 46, 3391. [all data]

Selim and Helal, 1981
Selim, E.T.M.; Helal, A.I., Heat of formation of CH2=OH+ fragment ion, Indian J. Pure Appl. Phys., 1981, 19, 977. [all data]

Lambdin, Tuffly, et al., 1959
Lambdin, W.J.; Tuffly, B.L.; Yarborough, V.A., Appearance potentials as obtained with an analytical mass spectrometer, Appl. Spectry., 1959, 13, 71. [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]

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]

Boand, Houriet, et al., 1983
Boand, G.; Houriet, R.; Baumann, T., The gas phase acidity of aliphatic alcohols, J. Am. Chem. Soc., 1983, 105, 2203. [all data]

Meot-Ner, 1984
Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [all data]

Wojtyniak and Stone, 1986
Wojtyniak, A.C.M.; Stone, A.J., A High-Pressure Mass Spectrometric Study of the Bonding of Trimethylsilylium to Oxygen and Aromatic Bases, Can. J. Chem., 1986, 74, 59. [all data]

Stone and Splinter, 1984
Stone, J.A.; Splinter, D.E., A high-pressure mass spectrometric study of the binding of (CH3)3Sn+ to lewis bases in the gas phase, Int. J. Mass Spectrom. Ion Processes, 1984, 59, 169. [all data]

Larson and McMahon, 1982
Larson, J.W.; McMahon, T.B., Formation, Thermochemistry, and Relative Stabilities of Proton - Bound dimers of Oxygen n - Donor Bases from Ion Cyclotron Resonance Solvent - Exchange Equilibria Measurements, J. Am. Chem. Soc., 1982, 104, 23, 6255, https://doi.org/10.1021/ja00387a016 . [all data]

Grimsrud and Kebarle, 1973
Grimsrud, E.P.; Kebarle, P., Gas Phase Ion Equilibria Studies of the Solvation of the Hydrogen Ion by Methanol, Dimethyl Ether and Water. Effect of Hydrogen Bonding, J. Am. Chem. Soc., 1973, 95, 24, 7939, https://doi.org/10.1021/ja00805a002 . [all data]

Lias, Liebman, et al., 1984
Lias, S.G.; Liebman, J.F.; Levin, R.D., Evaluated gas phase basicities and proton affinities of molecules heats of formation of protonated molecules, J. Phys. Chem. Ref. Data, 1984, 13, 695. [all data]

Sieck and Meot-ner, 1989
Sieck, L.W.; Meot-ner, M., Ionic Hydrogen Bond and Ion Solvation. 8. RS-..HOR Bond Strengths. Correlation with Acidities., J. Phys. Chem., 1989, 93, 4, 1586, https://doi.org/10.1021/j100341a079 . [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]

Larson and McMahon, 1984, 2
Larson, J.W.; McMahon, T.B., Gas phase negative ion chemistry of alkylchloroformates, Can. J. Chem., 1984, 62, 675. [all data]

Wilkinson, Szulejko, et al., 1992
Wilkinson, F.E.; Szulejko, J.E.; Allison, C.E.; Mcmahon, T.B., Fourier Transform Ion Cyclotron Resonance Investigation of the Deuterium Isotope Effect on Gas Phase Ion/Molecule Hydrogen Bonding Interactions in Alcohol-Fluoride Adduct Ions, Int. J. Mass Spectrom., 1992, 117, 487-505, https://doi.org/10.1016/0168-1176(92)80110-M . [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]

Rodgers and Armentrout, 2000
Rodgers, M.T.; Armentrout, P.B., Noncovalent Metal-Ligand Bond Energies as Studied by Threshold Collision-Induced Dissociation, Mass Spectrom. Rev., 2000, 19, 4, 215, https://doi.org/10.1002/1098-2787(200007)19:4<215::AID-MAS2>3.0.CO;2-X . [all data]

Operti, Tews, et al., 1988
Operti, L.; Tews, E.C.; Freiser, B.S., Determination of Gas-Phase Ligand Binding Energies to Mg+ by FTMS Techniques, J. Am. Chem. Soc., 1988, 110, 12, 3847, https://doi.org/10.1021/ja00220a020 . [all data]

Rodgers and Armentrout, 1999
Rodgers, M.T.; Armentrout, P.B., Absolute Binding Energies of Sodium Ions to Short-Chain Alcohols, CnH2n+2O, n=1-4, Determined by Threshold Collision-Induced Dissociation Experiments and Ab Initio Theory, 1999, 4955. [all data]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]


Notes

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