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Relative acidities and structure analysis of cis and trans isomers of 1,5‐oxazaspiro[5.5] undecane derivatives by multinuclear magnetic resonance
Author(s) -
GuerreroÁlvarez Jorge Antonio,
MasKu Wendy Paloma,
GarcíasMorales Cesar,
ArizaCastolo Armando
Publication year - 2010
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2592
Subject(s) - undecane , chemistry , substituent , titration , cis–trans isomerism , resonance (particle physics) , carbon 13 nmr , base (topology) , stereochemistry , crystallography , organic chemistry , mathematical analysis , physics , mathematics , particle physics
The relative acidities of the cis and trans isomers of a series of 1,5‐oxazaspiro[5.5]undecane derivatives were determined by measuring Δp K in acid‐base titrations followed by 1 H NMR. Relative structural stabilities were determined by measuring substituent chemical shift and γ‐gauche effects in 13 C, 15 N, and 17 O NMR. Crystallographic characterization of a model spiro[5.5]undecane is presented to support the basicity in solid state. Copyright © 2010 John Wiley & Sons, Ltd.