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- W2032038427 abstract "Substituent Effects on the Strength of CC-Bonds. IX. Thermolability of 2,3-Di(N,N-dialkylamino)-diethyl-succinates The title compounds meso and D, L 3a–c have been prepared from R,R′NCH2-COOEt (5), R,R′ = CH3 (a), C2H5 (b) and i-C3H7 (c), by lithiation followed by oxidation with I2. The thermolysis of 3 above 140°C in solution generates the radicals 1, which could be detected by e.s.r. Kinetic measurements are performed in the presence of a phenylthiol as a scavenger and the activation parameters are determined. – The steric acceleration of the cleavage reaction is separated using the correlation ΔG≠(300°C) = a Ds + b, whereby the strain values Ds = Hs (3) – 2 Hs (1)) are taken from force field calculations. The obtained strain free barrier to dissociation b = 37.4 kcal/mol is considerably lower than the value for the thermolysis reaction of tetraalkyl ethanes (b = 66.2kcal/mol [17]). The decrease of the activation enthalpy (ΔΔH≠ = 35.4kcal/mol) is mainly caused by stabilisation of 1 compared to sec. alkyl radicals; heats of formation of meso-3a and 5a support this conclusion. Furthermore, the decrease of bond strength in 3 by the two geminal capto-dative substituents exceeds the sum of the effect of one ester group (ΔΔH≠ = 4kcal/mol [19]) and one amino group (ΔΔH≠ = 9.5kcal/mol, drawn from the thermolysis of 1,2-(N,N-Dimethylamino)-1,2-diphenyl-ethane (4) by about 4 kcal/mol." @default.
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- W2032038427 date "1990-01-01" @default.
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- W2032038427 title "Substituenteneffekte auf die CC-Bindungsstärke. IX. Thermolabilität der 2,3-Di(N,N-dialkylamino)-bernsteinsäure-diethylester" @default.
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- W2032038427 doi "https://doi.org/10.1002/prac.19903320308" @default.
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