Computational and Experimental Studies Into the Conformations of a Triptycene-Based Ditopic Ligand

Jesús Sanmartín-Matalobos; Ana García-Deibe; Martín Amoza; Matilde Fondo; Antonio Mota; Sourav Sourav Bhowmick; Neeladri Das

doi:10.3390/ecsoc-18-e007

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Computational and Experimental Studies Into the Conformations of a Triptycene-Based Ditopic Ligand

Jesús Sanmartín-Matalobos

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1},

¹,

¹,

¹,

²,

Sourav Sourav Bhowmick

³,

Neeladri Das

¹ Coordination and Supramolecular Chemistry Group (Suprametal), Institute of Materials (iMATUS), Department of Inorganic Chemistry, Faculty of Chemistry, Universidade de Santiago de Compostela, Avenida das Ciencias s/n, 15782 Santiago de Compostela, Spain
² Departamento de Química Inorgánica. Facultad de Ciencias. Universidad de Granada. 18002 Granada. Spain
³ Department of Chemistry. Indian Institute of Technology (IIT) of Patna. Patna, Bihar, 800013. INDIA

Published: 31 October 2014 by MDPI in The 18th International Electronic Conference on Synthetic Organic Chemistry session Computational Chemistry

https://doi.org/10.3390/ecsoc-18-e007

Abstract: We present a combined computational and experimental study of the possible conformations adopted by a ditopic Schiff base ligand based on triptycene. We have performed DFT calculations on a Y-shaped Schiff base ligand derived from the condensation of 2,6-diaminotriptycene and 2 hydroxybenzaldehyde to obtain the relative energies of their conformers anti-s-cis, syn and anti-s-trans. Since these conformations are practically isoenergetic, interconversions of conformers proceed by rotation about C-N single bonds. NMR spectroscopy shows the presence in solution of the syn conformer, which is stable at room temperature on the NMR time scale.

Keywords: DFT calculations; Triptycene; Schiff base; Conformational isomerism

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