The Stabilizing Role of the Intramolecular C-H···O Hydrogen Bond in Cyclic Amides Derived From α-Methylbenzylamine.
作者信息
Sandoval-Lira Jacinto, Fuentes Lilia, Quintero Leticia, Höpfl Herbert, Hernández-Pérez Julio M, Terán Joel L, Sartillo-Piscil Fernando
机构信息
†Centro de Investigación de la Facultad de Ciencias Químicas and Centro de Química de la Benemérita, Universidad Autónoma de Puebla, México. 14 Sur Esq. San Claudio, San Manuel, C. P. 72570, Puebla, México.
‡Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, C. P. 62209, Cuernavaca, México.
出版信息
J Org Chem. 2015 May 1;80(9):4481-90. doi: 10.1021/acs.joc.5b00286. Epub 2015 Apr 14.
A series of five-, six-, seven-, and eight-membered lactams containing the chiral auxiliary α-methylbenzylamine were structurally analyzed and further studied by DFT calculations with the purpose to examine with detail the previously detected intramolecular C-H···O hydrogen-bonding interaction formed between the hydrogen atom of the α-methylbenzylamine and the carbonyl group of the cyclic amide. The main objective was to establish whether its presence does have a tangible relevance in their spatial arrangement in solution and in the solid state or is a simple and not stabilizing interaction.
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