1,8-bis(2-hydroxy-3,5-di-tert-butylbenzyl)-4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane

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Aranburu Leiva, AI, Kaur, M, Benjamin, SL ORCID: https://orcid.org/0000-0002-5038-1599, Jones, AM, Langley, SK and Mewis, RE, 2017. 1,8-bis(2-hydroxy-3,5-di-tert-butylbenzyl)-4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane. Molbank, 2017 (4), M963. ISSN 1422-8599

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Official URL: http://doi.org/10.3390/M963

Abstract

A cyclam (1,4,8,11-tetraazacyclotetradecane)-based macrocycle bearing two benzyl and two 2-hydroxy-3,5-di-tert-butylbenzyl pendent arms was synthesized and characterized using spectroscopic techniques and single crystal X-ray diffraction. The macrocycle crystallizes in the triclinic space group P-1, with the asymmetric unit containing one-half of the molecule. The structure is stabilized by hydrogen-bonding which exists between the phenolic protons and the nitrogen atoms of the macrocyclic ring. The presence of this hydrogen bonding is observed in the 1H-NMR due to the deshielded nature of the phenolic OH peak (δ 9.99). Cyclic voltammetry of the ligand revealed a single quasi-reversible peak at −0.58 V (Epc = −0.48 V and Epa = −0.68 V), which is due to the electrochemical oxidation of the phenol to the phenoxyl radical.

Item Type:	Journal article
Publication Title:	Molbank
Creators:	Aranburu Leiva, A.I., Kaur, M., Benjamin, S.L., Jones, A.M., Langley, S.K. and Mewis, R.E.
Publisher:	MDPI
Date:	13 October 2017
Volume:	2017
Number:	4
ISSN:	1422-8599
Identifiers:	Number Type 10.3390/M963 DOI M963 Publisher Item Identifier
Rights:	© 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.
Divisions:	Schools > School of Science and Technology
Record created by:	Jonathan Gallacher
Date Added:	04 Dec 2017 15:35
Last Modified:	04 Dec 2017 15:35
URI:	https://irep.ntu.ac.uk/id/eprint/32127