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Molecules 2017, 22(3), 361; doi:10.3390/molecules22030361

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

Centro de Investigación de la Facultad de Ciencias Químicas, and Centro de Química de la Benemérita Universidad Autónoma de Puebla, 14 Sur Esq. San Claudio, San Manuel. C. P. 72570 Puebla, Mexico
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Authors to whom correspondence should be addressed.
Academic Editor: Steve Scheiner
Received: 2 February 2017 / Revised: 22 February 2017 / Accepted: 24 February 2017 / Published: 28 February 2017
(This article belongs to the Special Issue Intramolecular Hydrogen Bonding 2017)
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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. View Full-Text
Keywords: C−H···O interaction; chiral lactams; α-methylbenzylamine; MP2 C−H···O interaction; chiral lactams; α-methylbenzylamine; MP2
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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.

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