38557-29-8Relevant articles and documents
Vibrational Spectra and Conformations of (Iodomethyl)cyclopropane and Epiiodohydrin
Wurrey, C. J.,Yeh, Y. Y.,Krishnamoorthi, R.,Berry, R. J.,DeWitt, J. E.,Kalasinsky, V. F.
, p. 4059 - 4063 (1984)
The infrared (4000-400 cm-1) spectra of (iodomethyl)cyclopropane and epiiodohydrin in all three physical states have been recorded.The Raman (3500-50 cm-1) spectra of these two molecules in condensed phases have also been obtained.For (iodomethyl)cyclopropane no multiple Q branches were observed in the gase-phase infrared spectrum nor were any liquid-phase peaks observed to vanish upon crystallization.On the basis of these data and on the liquid-phase Raman depolarization ratios (which suggest that all observed Raman lines are polarized) it has been concluded that (iodomethyl)cyclopropane exists solely in the (nonsymmetric) gauche conformation in all states of matter.On the other hand, epiiodohydrin exhibits several gas-phase infrared band contours with "extra" Q branches and ten liquid-phase Raman conformer doublets, wherein one member of each doublet disappears when the annealed solid phase is obtained.These data have been interpreted in terms of a gauche-1 (70percent)/gauche-2 (30percent) conformational equilibrium for liquid epiiodohydrin at room temperature, with only the gauche-1 conformer remaining in the crystalline sample.From a variable-temperature (-74 to 25 deg C) study of the base-line-resolved liquid-phase Raman doublet at 940/914 cm-1, an enthalpy difference between conformers of 0.50 +/- 0.05 kcal/mol has been determined, with the gauche-1 conformer the more stable.No evidence for a cis conformation of either molecule was found, apparently as a result of strong steric interactions between the iodine atom and β-ring hydrogen atoms.For these molecules, vibrational assignments, which are in excellent agreement with the vibrational assignments of other (halomethyl)cyclopropanes and epihalohydrins, have also been proposed.
ELECTROPHILIC ADDITION TO BICYCLOBUTANE>
Abramova, N. M.,Zotova, S. V.,Nesmeyanova, O. A.
, p. 961 - 964 (2007/10/02)
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