Influence of methyl substituents on the stability of 1-aza-2-adamantanone, Kirby's most twisted amide

Autor:	Kathleen M. Morgan, Margo N. Montgomery, M. Logan Rawlins
Rok vydání:	2005
Předmět:	chemistry.chemical_classification Hydrolysis chemistry.chemical_compound chemistry Adamantane Amide Organic Chemistry Thorpe–Ingold effect Organic chemistry Physical and Theoretical Chemistry Medicinal chemistry Amino acid
Zdroj:	Journal of Physical Organic Chemistry. 18:310-314
ISSN:	1099-1395 0894-3230
DOI:	10.1002/poc.855
Popis:	Hydrolysis and carbonyl hydration of adamantane-based twisted amide 1 were studied computationally. The importance of the bridgehead methyl substituents on these reactions was determined. The carbonyl hydration of 1 is structurally and energetically much like the hydration of a transition state to amide CN bond rotation. However, hydrolysis of 1 to the amino acid is dependent on the bridgehead methyl substituents and less like hydrolysis of an amide transition state. Copyright © 2004 John Wiley & Sons, Ltd.
Databáze:	OpenAIRE
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