title: The Stabilizing Role of the Intramolecular C-H···O Hydrogen Bond in Cyclic Amides Derived From α-Methylbenzylamine.
abstract: 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.
authors.affiliation: †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.
authors.forename: Jacinto
authors.initials: J
authors.lastname: Sandoval-Lira
authors.affiliation: †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.
authors.forename: Lilia
authors.initials: L
authors.lastname: Fuentes
authors.affiliation: †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.
authors.forename: Leticia
authors.initials: L
authors.lastname: Quintero
authors.affiliation: ‡Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, C. P. 62209, Cuernavaca, México.
authors.forename: Herbert
authors.initials: H
authors.lastname: Höpfl
authors.affiliation: †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.
authors.forename: Julio M
authors.initials: JM
authors.lastname: Hernández-Pérez
authors.affiliation: †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.
authors.forename: Joel L
authors.initials: JL
authors.lastname: Terán
authors.affiliation: †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.
authors.forename: Fernando
authors.initials: F
authors.lastname: Sartillo-Piscil