23169-87-1Relevant articles and documents
Unstable Enols in the Gas Phase. Preparation, Ionization Energies, and Heats of Formation of (E)- and (Z)-2-Buten-2-ol, 2-Methyl-1-propen-1-ol, and 3-Methyl-2-buten-2-ol
Turecek, Frantisek,Brabec, Libor,Korvola, Jorma
, p. 7984 - 7990 (2007/10/02)
(E)-2-Buten-2-ol (1), (Z)-2-buten-2-ol (2), 2-methyl-1-propen-1-ol, and 3-methyl-2-buten-2-ol (4) were prepared as transient species by flash-vacuum pyrolysis of the corresponding methylated bicyclohept-5-en-2-ols and characterized by mass spectrometry.Treshold ionization energies (IE) were determined as IE(1) = 8.42 +/- 0.04, IE(2) = 8.44 +/- 0.03, IE(3) = 8.44 +/- 0.03, and IE(4) = 8.15 +/- 0.04 eV.Cation radical .+ was generated from 3,3-dimethyl-2-hexanone, and its appearance energy and heat of formation were determined as AE = 9.33 +/- 0.09 eV and ΔHf0 = 545 +/- 10 kJ*mol-1.The heats of formation of the neutral enols 1 - 4 were determined as -212, -214, -207, and -241 kJ*mol-1, respectively.The experimental heats of formation are compared with those predicted from Benson's additivity rules or calculated by the semiempirical MNDO method.Substituent effects on the heats of formation, proton affinities, and relative thermochemical and kinetic stabilities of simple enols are discussed.