title: A quantitative structure-reactivity relationship in N-acetyl oxazolidines: an electrostatic interaction controls rotamer population.
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.
authors: Departamento de Química Orgánica e Inorgánica, QUOREX Research Group, Facultad de Ciencias-UEX, E-06006, Badajoz, Spain. rmarvaz@unex.es
authors: R Fernando
authors: RF
authors: Martínez
authors: Martín
authors: M
authors: Ávalos
authors: Reyes
authors: R
authors: Babiano
authors: Pedro
authors: P
authors: Cintas
authors: José L
authors: JL
authors: Jiménez
authors: Juan C
authors: JC
authors: Palacios
authors: Esther M S
authors: EM
authors: Pérez
mesh_terms: D000107:Acetylation; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D055672:Static Electricity; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D010080:Oxazoles; C064210:oxazolidine