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Volume 70, Issue 9

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Synthesis, structural and spectroscopic properties of asymmetric schiff bases derived from 2,3-diaminopyridine

Agnieszka Pazik
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  • Department of Chemistry and Technology of Functional Materials, Narutowicza Street 11/12, 80-233 Gdansk, Poland
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/ Beata Kamińska
  • Department of Chemistry and Technology of Functional Materials, Narutowicza Street 11/12, 80-233 Gdansk, Poland
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/ Anna Skwierawska
  • Department of Chemistry and Technology of Functional Materials, Narutowicza Street 11/12, 80-233 Gdansk, Poland
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/ Łukasz Ponikiewski
  • Department of Inorganic Chemistry, Gdansk University of Technology, Narutowicza Street 11/12, 80-233 Gdansk, Poland
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Published Online: 2016-05-24 | DOI: https://doi.org/10.1515/chempap-2016-0058

Abstract

Two Schiff base derivatives, 4-(2-amino-3-pyridyliminomethyl)phenol (I) and 3-(2-amino-3- pyridyliminomethyl)nitrobenzene (II ), were synthesised and characterised by spectroscopy. The structure of I was determined by single crystal X-ray diffraction studies. The asymmetric Schiff base derived from 2,3-diaminopyridine selectively recognise transition and heavy metal cations, and some anion. Ligands I and II form stable complexes with Cu2+, Zn2+, Pb2+, Al3+ whereas ligand I also binds F ions. The stoichiometry for the host : cation is 1 : 1 and 2 : 1. The addition of F ion in CH3CN to ligand I causes a colour change of the solution from colourless to yellow. The binding behaviour of ligand I towards several ions was investigated using density functional theory calculations.

Key words: asymmetric Schiff bases; X-ray crystal structure; cation complexation; fluoride; UVVISspectroscopy; 1H NMR spectroscopy

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About the article

Received: 2015-10-26

Revised: 2016-01-21

Accepted: 2016-02-04

Published Online: 2016-05-24

Published in Print: 2016-09-01


Citation Information: Chemical Papers, Volume 70, Issue 9, Pages 1204–1217, ISSN (Online) 1336-9075, ISSN (Print) 0366-6352, DOI: https://doi.org/10.1515/chempap-2016-0058.

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