A new anilido-imine compound containing o-OMe-anilinyl derived from an unexpected adduct: Synthesis, crystal structure and its coordination capability - 25/03/14

Doi : 10.1016/j.crci.2013.09.005

Qing Su ^a, Pei Li ^a, Mina He ^a, Qiaolin Wu ^a,^⁎ , Ling Ye ^b, Ying Mu ^a,^b,^⁎, Yudan Ma ^c
^a School of Chemistry, Jilin University, 2699 Qianjin Street, Chang Chun 130012, People's Republic of China
^b State Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699 Qianjin Street, Chang Chun 130012, People's Republic of China
^c Sports Science Research Institute of Jilin Province, 2476 Ziyou Road, Changchun 130022, People's Republic of China

^⁎Corresponding authors.

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Abstract

A new compound, ortho-C₆H₄F[CH(NHC₆H₄OMe-2)₂], 1, was obtained with ortho-flurobenzaldehyde and 2-methoxyaniline as the starting materials. Compound 1 was readily converted into ortho-C₆H₄(2-OMeC₆H₄)(CHNC₆H₄OMe-2) 2 after treatment with 1 equiv of n-BuLi. Treatment of compound 2 with 1.5 equiv of ZnEt₂ afforded the trinuclear zinc complex 3 by alkyl elimination and alkylation of the imino group of the ligand. The molecular structures of two new organic compounds and of the trinuclear zinc complex were determined by single-crystal X-ray diffraction. The dianionic ONNO tetradentate ligands derived from compound 2 coordinate to zinc ions in four to five coordination modes, forming distorted tetrahedral and trigonal–bipyramidal geometry around three metal centers.

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Keywords : Anilido-imine compound, Crystal structure, Schiff bases, Supramolecular chemistry, Zinc complexes

Plan

Introduction

Experimental

General comments

Synthesis of ortho-C₆H₄F[CH(NHC₆H₄OMe-2)₂] (1)

Synthesis of ortho-C₆H₄(2-OMeC₆H₄)(CHNC₆H₄OMe-2) (2)

Synthesis of trinuclear zinc complex 3

X-ray structure determinations of 1–3

Results and discussion

Synthesis of compounds 1 and 2

Synthesis of trinuclear zinc complex 3

The probable mechanisms for the formation of anilido-imine 2

Crystal structures of 1–3

Conclusions

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Vol 17 - N° 4

P. 377-385 - avril 2014 Retour au numéro

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A new anilido-imine compound containing o-OMe-anilinyl derived from an unexpected adduct: Synthesis, crystal structure and its coordination capability - 25/03/14

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