Crystal structure of the di-Mannich base 4,4′-di­chloro-3,3′,5,5′-tetra­methyl-2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol

  • The title compound, C21H26Cl2N2O2, was prepared in a solvent-free microwave-assisted synthesis, and crystallizes in the ortho­rhom­bic space group Pna21. The imidazolidine ring adopts an envelope conformation and its mean plane is almost perpendicular to the two pendant aromatic rings [dihedral angles = 84.61 (9) and 86.54 (9)°]. The mol­ecular structure shows the presence of two intra­molecular O—H⋯N hydrogen bonds between the phenolic hy­droxy groups and imidazolidine N atoms. The two 3-chloro-6-hy­droxy-2,4-di­methyl­benzyl groups are located in a cis orientation with respect to the imidazolidine fragment. As a result, the lone pairs of electrons on the N atoms are presumed to be disposed in a syn conformation. This is therefore the first example of an exception to the `rabbit-ears' effect in such 2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol derivatives.

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Author:Augusto RiveraORCiD, Luz Stella Nerio, Michael BolteORCiD
Pubmed Id:
Parent Title (English):Acta crystallographica. Section E, Crystallographic communications
Publisher:International Union of Crystallography ; National Center for Biotechnology Information, U.S. National Library of Medicine
Place of publication:Chester ; Bethesda, MD
Contributor(s):J. Simpson
Document Type:Article
Year of Completion:2015
Date of first Publication:2015/02/25
Publishing Institution:Universitätsbibliothek Johann Christian Senckenberg
Release Date:2020/06/17
Tag:crystal structure; diMannich base; hydrogen bonding; imidazolidine; syn conformation
Page Number:9
First Page:312
Last Page:314
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Institutes:Biochemie, Chemie und Pharmazie / Biochemie und Chemie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Licence (German):License LogoCreative Commons - Namensnennung 2.0