Effect of carbonyl substituents on the barrier to rotation in N??ethyl??N??methylamides

HG Bonacorso, MSB Caro, N Zanatta…

Index: Bonacorso, Helio G.; Caro, Miguel S. B.; Zanatta, Nilo; Martins, Marcos A. P. Magnetic Resonance in Chemistry, 1993 , vol. 31, # 5 p. 451 - 454

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Citation Number: 9

Abstract

Abstract The barriers to rotation about the C (O)[BOND] N bond for 13 α-alkyl-and α-halo- substituted N-theyl-N-methylamides were determined by 1 H NMR spectroscopy at coalescence temperature. Plots of Gibbs free energy (ΔG) and Gibbs energy of activation (ΔG‡) values against Charton's electronic and steric parameters of the α-carbonyl groups allows the conclusion that both the isomeric preference and the barrier to rotation about ...