Relative acidities and structure analysis of cis and trans isomers of 1,5‐oxazaspiro[5.5] undecane derivatives by multinuclear magnetic resonance |
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| Authors: | Jorge Antonio Guerrero‐Álvarez Wendy Paloma Mas‐Ku Cesar Garcías‐Morales Armando Ariza‐Castolo |
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| Institution: | 1. Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad No. 1001, Col. Chamilpa, Cuernavaca Morelos 62210, Mexico;2. Departamento de Química, Centro de Investigación y de Estudios Avanzados del IPN, Av. IPN 2508 Col. San Pedro Zacatenco 07360, apartado postal 14‐740, 07000 México, D.F. |
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| Abstract: | The relative acidities of the cis and trans isomers of a series of 1,5‐oxazaspiro5.5]undecane derivatives were determined by measuring ΔpK in acid‐base titrations followed by 1 H NMR. Relative structural stabilities were determined by measuring substituent chemical shift and γ‐gauche effects in 13C, 15N, and 17O NMR. Crystallographic characterization of a model spiro5.5]undecane is presented to support the basicity in solid state. Copyright © 2010 John Wiley & Sons, Ltd. |
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| Keywords: | NMR titration acidity spiro compounds X‐ray diffraction |
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