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Intramolecular Hydrogen Bond Activation of Aza‐Methylene Imines in Hydrogen Bond Bifunctional Catalysis – A Density Functional Theory Study
Author(s) -
MartínSómer Ana,
Arpa Enrique M.,
DíazTendero Sergio,
Alemán José
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801208
Subject(s) - chemistry , intramolecular force , intermolecular force , density functional theory , hydrogen bond , bifunctional , reactivity (psychology) , cycloaddition , covalent bond , catalysis , low barrier hydrogen bond , functional group , computational chemistry , photochemistry , organic chemistry , molecule , medicine , polymer , alternative medicine , pathology
In this work, we present a density functional theory study of the dipolar cycloaddition of azamethylene imines to nitroalkenes, showing the importance of the intramolecular activation of the hydroxyl group and the role of the intermolecular hydrogen bond with Takemoto's catalyst. The importance of non‐covalent interactions is evaluated by means of simulations using non‐covalent interactions, and natural bonding orbital analysis. The combination of these studies allows us to understand the role played by the intra‐ and intermolecular interactions in the reactivity and enantioselectivity of the process.