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Looking Inside the Intramolecular C-H∙∙∙O Hydrogen Bond in Lactams Derived From α-Methylbenzylamine

Looking Inside the Intramolecular C-H∙∙∙O Hydrogen Bond in Lactams Derived From α-Methylbenzylamine

Sandra Mejía, Julio M Hernández-Pérez, Jacinto Sandoval-Lira, Fernando Sartillo-Piscil

Molecules. 2017 Feb 28;22(3):361.

PMID: 28264508

Abstract:

Recently, 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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2627863	(S)-(−)-α-Methylbenzylamine		2627-86-3	Price

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