On the origin of the axial behaviour of 5??halomethyl groups in 1, 3??dioxane. Evidence for non??bonded electrostatic attraction

F Borremans, MJO Anteunis

Index: Borremans,F.; Anteunis,M.J.O. Bulletin des Societes Chimiques Belges, 1976 , vol. 85, p. 681 - 696

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Citation Number: 5

Abstract

Abstract The conformational behaviour of the halomethyl group in 5-position in 1, 3- dioxanes is determined quantitatively by low temperature nuclear magnetic resonance, and the origin of the axial preference of ca. 1 kcal. mole− 1 relative to the 5-methyl group is disclosed and discussed in terms of a local electrostatic attraction in XC-CC (H) Y fragments, having a double gauche conformation (X, Y electronegative elements).