Looking Inside the Intramolecular C−H∙∙∙O Hydrogen Bond in Lactams Derived from α-Methylbenzylamine
AbstractRecently, strong evidence that supports the presence of an intramolecular C−H···O hydrogen bond in amides derived from the chiral auxiliary α-methylbenzylamine was disclosed. Due to the high importance of this chiral auxiliary in asymmetric synthesis, the inadvertent presence of this C−H···O interaction may lead to new interpretations upon stereochemical models in which this chiral auxiliary is present. Therefore, a series of lactams containing the chiral auxiliary α-methylbenzylamine (from three to eight-membered ring) were theoretically studied at the MP2/cc-pVDZ level of theory with the purpose of studying the origin and nature of the C−Hα···O interaction. NBO analysis revealed that rehybridization at C atom of the C−Hα bond (s-character at C is ~23%) and the subsequent bond polarization are the dominant effect over the orbital interaction energy n(O)→σ*C−Hα (E(2) < 2 kcal/mol), causing an important shortening of the C−Hα bond distance and an increment in the positive charge in the Hα atom. View Full-Text
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Mejía, S.; Hernández-Pérez, J.M.; Sandoval-Lira, J.; Sartillo-Piscil, F. Looking Inside the Intramolecular C−H∙∙∙O Hydrogen Bond in Lactams Derived from α-Methylbenzylamine. Molecules 2017, 22, 361.
Mejía S, Hernández-Pérez JM, Sandoval-Lira J, Sartillo-Piscil F. Looking Inside the Intramolecular C−H∙∙∙O Hydrogen Bond in Lactams Derived from α-Methylbenzylamine. Molecules. 2017; 22(3):361.Chicago/Turabian Style
Mejía, Sandra; Hernández-Pérez, Julio M.; Sandoval-Lira, Jacinto; Sartillo-Piscil, Fernando. 2017. "Looking Inside the Intramolecular C−H∙∙∙O Hydrogen Bond in Lactams Derived from α-Methylbenzylamine." Molecules 22, no. 3: 361.