Mannich Bases as Model Compounds for Intramolecular Hydrogen Bonding II [1]. Structure and Properties in Solution

1999 ◽  
Vol 130 (8) ◽  
pp. 983-1001 ◽  
Author(s):  
Aleksander Koll ◽  
Peter Wolschann
Keyword(s):  
Hydrogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
Mannich Bases ◽  
Structure And Properties ◽  
Model Compounds ◽  
Intramolecular Hydrogen

Seven-Membered Intramolecular Hydrogen Bonding of Phenols: Database Analysis and Phloroglucinol Model Compounds

2012 ◽  
Vol 2012 (24) ◽  
pp. 4483-4492 ◽  
Author(s):  
Ronald K. Castellano ◽  
Yan Li ◽  
Edwin A. Homan ◽  
Andrew J. Lampkins ◽  
Iris V. Marín ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
Model Compounds ◽  
Database Analysis ◽  
Intramolecular Hydrogen

scholarly journals Microwave-Assisted Synthesis of Mono- and Disubstituted 4-Hydroxyacetophenone Derivatives via Mannich Reaction: Synthesis, XRD and HS-Analysis

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 590 ◽  
Author(s):  
Ghadah Aljohani ◽  
Musa Said ◽  
Dieter Lentz ◽  
Norazah Basar ◽  
Arwa Albar ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
Chair Conformation ◽  
Mannich Bases ◽  
Secondary Amines ◽  
Microwave Assisted Synthesis ◽  
Microwave Assisted ◽  
Regioselective Substitution ◽  
Intramolecular Hydrogen ◽  
Methyl Phenyl

An efficient microwave-assisted one-step synthetic route toward Mannich bases is developed from 4-hydroxyacetophenone and different secondary amines in quantitative yields, via a regioselective substitution reaction. The reaction takes a short time and is non-catalyzed and reproducible on a gram scale. The environmentally benign methodology provides a novel alternative, to the conventional methodologies, for the synthesis of mono- and disubstituted Mannich bases of 4-hydroxyacetophenone. All compounds were well-characterized by FT-IR, 1H NMR, 13C NMR, and mass spectrometry. The structures of 1-{4-hydroxy-3-[(morpholin-4-yl)methyl]phenyl}ethan-1-one (2a) and 1-{4-hydroxy-3-[(pyrrolidin-1-yl)methyl]phenyl}ethan-1-one (3a) were determined by single crystal X-ray crystallography. Compound 2a and 3a crystallize in monoclinic, P21/n, and orthorhombic, Pbca, respectively. The most characteristic features of the molecular structure of 2a is that the morpholine fragment adopts a chair conformation with strong intramolecular hydrogen bonding. Compound 3a exhibits intermolecular hydrogen bonding, too. Furthermore, the computed Hirshfeld surface analysis confirms H-bonds and π–π stack interactions obtained by XRD packing analyses.

scholarly journals Intramolecular Hydrogen Bonds in Selected Aromatic Compounds: Recent Developments

Catalysts ◽  
2019 ◽  
Vol 9 (11) ◽  
pp. 909
Author(s):  
Aneta Jezierska ◽  
Peter M. Tolstoy ◽  
Jarosław J. Panek ◽  
Aleksander Filarowski
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Aromatic Compounds ◽  
Mannich Base ◽  
Intramolecular Hydrogen Bonding ◽  
Mannich Bases ◽  
Intramolecular Hydrogen Bonds ◽  
Recent Developments ◽  
Physicochemical Features ◽  
Intramolecular Hydrogen

A review of intramolecular hydrogen bonding in ortho-hydroxyaryl Schiff bases, ortho-hydroxyaryl Mannich bases, dipyrrins, ortho-hydroxyaryl ketones, ortho-hydroxyaryl amides, and 4-Bora-3a,4a-diaza-s-indacene (BODIPY) dyes with tautomeric sensors as substituents is presented in this paper. Ortho-hydroxy Schiff and Mannich base derivatives are known as model molecules for analysing the properties of intramolecular hydrogen bonding. The compounds under discussion possess physicochemical features modulated by the presence of strong intramolecular hydrogen bonds. The equilibrium between intra- and inter-molecular hydrogen bonds in BODIPY is discussed. Therefore, the summary can serve as a knowledge compendium of the influence of the hydrogen bond on the molecular properties of aromatic compounds.

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