| Schiff base macrocycles containing pyrroles and pyrazoles. | |
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MedLine Citation:
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PMID: 18421738 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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A double nucleophilic substitution reaction of 3,5-bis(chloromethyl)pyrazole with pyrroles generates a novel pyrrole-pyrazole hybrid building block, the pyrazole analogue to tripyrrane. Vilsmeier-Haack formylation produces the corresponding dialdehyde, which was used in the formation of a series of nonaromatic Schiff base macrocycles. NMR and UV/Vis spectroscopy and single-crystal diffractometry were used to characterize the novel macrocycles. The solid-state structures of select free bases and protonated members of this class of macrocycles display a range of intra- and intermolecular hydrogen-bonding patterns that suggest their use in molecular-recognition systems. They also contain an acid-sensitive chromophore. Their acid-base and anion-recognition properties were ascertained; alas, only modest anion-selective spectroscopic signatures could be detected by using UV/Vis and (1)H NMR spectroscopy. The macrocycles proved resistant toward oxidation to their aromatic congeners. The pyrrole-pyrazole building blocks presented are potentially useful for the synthesis of a range of pyrazole analogues of all-pyrrole macrocycles. |
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Authors:
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Stamatia Katsiaouni; Sebastian Dechert; Raymond P Briñas; Christian Brückner; Franc Meyer |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Chemistry (Weinheim an der Bergstrasse, Germany) Volume: 14 ISSN: 0947-6539 ISO Abbreviation: Chemistry Publication Date: 2008 |
Date Detail:
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Created Date: 2008-05-26 Completed Date: 2008-08-05 Revised Date: 2009-08-04 |
Medline Journal Info:
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Nlm Unique ID: 9513783 Medline TA: Chemistry Country: Germany |
Other Details:
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Languages: eng Pagination: 4823-35 Citation Subset: - |
Affiliation:
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Institut für Anorganische Chemie, Georg-August-Universität, Tammannstrasse 4, 37077 Göttingen, Germany. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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