A quantitative structure-reactivity relationship in N-acetyl oxazolidines: an electrostatic interaction controls rotamer population |
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| Authors: | Martínez R Fernando Ávalos Martín Babiano Reyes Cintas Pedro Jiménez José L Palacios Juan C Pérez Esther M S |
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| Institution: | Departamento de Química Orgánica e Inorgánica, QUOREX Research Group, Facultad de Ciencias-UEX, E-06006, Badajoz, Spain. rmarvaz@unex.es |
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| Abstract: | The conformational population of Z and E isomers of the amide bond in N-acetyl oxazolidines is dictated by the electronic nature of the vicinal aryl ring. Experimental and theoretical data support a rationale based on a strong and stereodirecting charge-charge interaction that should be added to the arsenal of non-covalent interactions and whose influence can be more important than once thought. |
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