Structure–reactivity relationships in the rate of esterification by acetylimidazole: the influence of the second hydroxy group and of the length of the N-ω-hydroxy-n-alkyl chain in 3-(N-methyl, N-ω-hydroxy-n-alkyl)amino-2- tert-butylpropan-1-ols

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Annemieke Madder, Pierre J. De Clercq and Howard Maskill


Enforced intramolecular hydrogen bonding facilitates intramolecular general base catalysis in the acetylation of a family of α,ω-amino alcohols by acetylimidazole, and the site of acetylation when there are two hydroxy groups is determined by the relative ease of intramolecular hydrogen bonding rather than by intermolecular steric effects.


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  9. Fig. 2 shows the minimum energy conformation of several lowenergy conformations found. Geometry calculated using Macromodel V3.0:W. C. Still, F. Mohamadi, N. G. J. Richards, W. C. Guida, M. Lipton, R. Liskamp, G. Chang, T. Hendrickson, F. DeGunst and W. Hasel, Department of Chemistry, Columbia University, New York, NY 10027, USA.