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Carbon–hydrogen bond strengths in methyl formate and the kinetics of the reaction with iodine

✍ Scribed by Richard K. Solly; Sidney W. Benson

Publisher
John Wiley and Sons
Year
1969
Tongue
English
Weight
507 KB
Volume
1
Category
Article
ISSN
0538-8066

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✦ Synopsis

The gas phase reaction I, + HCOOCH, +HI + CH,I + CO, has been studied spectrophotometrically in a static system over the pressure ranges I, (6-39 torr) and HCOOMe (28-360 torr). In the temperature range 293-356', the initial rate of disappearance of I, is first order in [HCOOMe] and half-order in [I,]. The rate determining step is I. f HCOOMe A HI + COOMe where k, is given by log,, (k,/M-lsec-l) = (9.6 f 0.3) -(22.4 i -0.8)/19

where 8 = 2.303 R T in kcal/mole. This activation energy gives a carbonyl C-H bond strength of 92.7 kcal/mole. At 356' there was no evidence of abstraction of a methoxy hydrogen, so a lower limit of 100 kcal/mole may be placed on this C-H bond strength. These ester C-H bond strengths are discussed in relation to comparable values in aldehydes and ethers.

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