Ethynol: a theoretical prediction of remarkably high gas-phase acidity

1989 ◽  
Vol 111 (21) ◽  
pp. 8297-8299 ◽  
Author(s):  
Brian J. Smith ◽  
Leo Radom ◽  
A. Jerry Kresge
Keyword(s):  
Theoretical Prediction ◽  
Gas Phase ◽  
Gas Phase Acidity

scholarly journals Experimental and Computational Studies on the Gas-Phase Acidity of 5,5-Dialkyl Barbituric Acids

2021 ◽  
Author(s):  
Juan Z. Dávalos-Prado ◽  
Javier González ◽  
Josep M. Oliva-Enrich ◽  
Emma J. Urrunaga ◽  
Alexsandre F. Lago
Keyword(s):  
Gas Phase ◽  
Computational Studies ◽  
Gas Phase Acidity

scholarly journals Gas-phase acidity of sulfonamides: implications for reactivity and prodrug design

Tetrahedron ◽  
2005 ◽  
Vol 61 (10) ◽  
pp. 2705-2712 ◽  
Author(s):  
J.R.B. Gomes ◽  
P. Gomes
Keyword(s):  
Gas Phase ◽  
Gas Phase Acidity

Gas-phase Acidity and Aromaticity of 1,2-dithiosquaric Acid

2000 ◽  
Vol 16 (01) ◽  
pp. 15-21
Author(s):  
Zhou Li-Xin ◽  
◽  
Mang Chao-Yong ◽  
Zhang Yong-Fan
Keyword(s):  
Gas Phase ◽  
Gas Phase Acidity

Theoretical prediction of proton and electron affinities, gas phase basicities, and ionization energies of sulfinamides

2019 ◽  
Vol 31 (1) ◽  
pp. 411-421
Author(s):  
Masoumeh Ghahremani ◽  
Hamed Bahrami ◽  
Hamed Douroudgari ◽  
Morteza Vahedpour
Keyword(s):  
Theoretical Prediction ◽  
Gas Phase ◽  
Electron Affinities ◽  
Ionization Energies ◽  
Gas Phase Basicities

Absolute gas-phase acidities of CH3NH2, C2H5NH2, (CH3)2 NH, and (CH3)3N

1976 ◽  
Vol 54 (10) ◽  
pp. 1624-1642 ◽  
Author(s):  
Gervase I. Mackay ◽  
Ronald S. Hemsworth ◽  
Diethard K. Bohme
Keyword(s):  
Equilibrium Constant ◽  
Gas Phase ◽  
Equilibrium Constants ◽  
Heats Of Formation ◽  
Molecular Orbital Calculations ◽  
Electron Affinities ◽  
Flowing Afterglow ◽  
Experimental Assessment ◽  
Gas Phase Acidity ◽  
Conjugate Bases

The flowing afterglow technique has been employed in measurements of the rate and equilibrium constants at 296 ± 2 K for reactions of the type[Formula: see text]and[Formula: see text]where R1 and R2 may be H, CH3, or C2H5. The equilibrium constant measurements provided absolute values for the intrinsic (gas-phase) acidities of the Brønsted acids CH3NH2, C2H5NH2, (CH3)2NH, and (CH3)3N, the heats of formation of their conjugate bases, and the electron affinities of the corresponding radicals R1R2N. Proton removal energies, ΔG0298/(kcal mol−1), were determined to be 395.7 ± 0.7 for [Formula: see text] 391.7 ± 0.7 for [Formula: see text] 389.2 ± 0.6 for [Formula: see text] and > 396 for [Formula: see text] Heats of formation, ΔH0f.,298, were determined to be 30.5 ± 1.5 for CH3NH−, 21.2 ± 1.5 for C2H5NH−, and 24.7 ± 1.4 for (CH3)2N−. Electron affinities (in kcal mol−1) were determined to be 13.1 ± 3.5 for CH3NH, 17 ± 4 for C2H5NH, and 14.3 ± 3.4 for (CH3)2N. These results quantify earlier conclusions regarding the intrinsic effects of substituents on the gas-phase acidity of amines and provide an experimental assessment of recent molecular orbital calculations of proton removal energies for alkylamines.

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