Synthesis, Crystal Structures, Density Functional Theory (DFT) Calculations and Molecular Orbital Calculations of Two Ne

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ORIGINAL PAPER

Synthesis, Crystal Structures, Density Functional Theory (DFT) Calculations and Molecular Orbital Calculations of Two New Metal‑Free Macrocyclic Schiff Bases Derived from 2,6‑Dibenzoyl‑4‑alkylphenol and Diamines Javeed A. Ganaie1 · Neha Sen1 · Ray J. Butcher2 · Jerry P. Jasinski3 · Sushil K. Gupta1 Received: 24 May 2018 / Accepted: 31 October 2019 © Springer Science+Business Media, LLC, part of Springer Nature 2019

Abstract Two new phenol-based metal-free macrocyclic Schiff bases, cyclo-bis{2-[benz(N-propan-1,3-diyl)imidoyl][6-benzimidoyl] [4-methyl]phenol} and cyclo-bis{2-[benz(N-butan-1,4-diyl)imidoyl][6-benzimidoyl][4-tert-butyl]phenol} have been synthesized and their structures determined by single crystal X-ray crystallography. The DFT geometry optimization calculations were performed to compare experimental and theoretical results. A comparison of the dihedral angles between mean planes of the central phenolato rings and peripheral phenyl rings in the crystal with the DFT theoretical calculations has been included for each molecule. Electronic transitions have been predicted by DFT molecular orbital calculations and compared with experimental absorption spectral data. Graphic Abstract A one-pot synthesis, crystal structure and theoretical calculations of 20- and 22-membered macrocyclic ligands are reported.

Keywords Phenol-based macrocyclic derivatives · Crystal structure · DFT geometry optimization calculations · DFT molecular orbital calculations Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10870-019-00812-6) contains supplementary material, which is available to authorized users. Extended author information available on the last page of the article

13

Vol.:(0123456789)

Journal of Chemical Crystallography

Introduction

Experimental

Macrocyclic Schiff bases have potential applications as models for protein metal binding sites, synthetic ionophores, magnetic exchange phenomena, therapeutic reagents, cyclic antibiotics, host–guest interaction and in phase transfer catalysis [1, 2]. A large variety of [1 + 1] and [2 + 2] macrocyclic ligands have been synthesised by a template procedure in the presence of suitable metal ions [3]. There are various reports of metal-free macrocycles [4–6] available in the literature involving cyclodextrines [7–12], shape persistent macrocycles [13–20] and crown ethers, spherands and cryptands [21–26]. We have previously reported the synthesis and crystal structure of a neutral tetraiminodiphenol macrocycle with a C2 lateral chain, cyclo-bis{2-[benz(Nethan-1,3-diyl)imidoyl][6-benzimidoyl] [4-methyl]phenol}, cyclo-[LMeH2] (n = 2) (I) [27]. As part of our study on phenol-based Schiff bases [28–32], we herein report the synthesis and crystal structures of cyclo-bis{2-[benz(Npropan-1,3-diyl)imidoyl][6-benzimidoyl][4-methyl]phenol}, Cyclo-[LMeH2] (n = 3) (II) and cyclo-bis{2-[benz(N-butan1,4-diyl)imidoyl][6-benzimidoyl][4-tert-butyl]phenol}, Cyclo-[Lt-BuH2] (n = 4) (III), and theoretical calculations of I,

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Synthesis, Crystal Structures, Density Functional Theory (DFT) Calculations and Molecular Orbital Calculations of Two Ne

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