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

Aranburu Leiva, A.I., Kaur, M., Benjamin, S.L. ORCID: 0000-0002-5038-1599, Jones, A.M., Langley, S.K. and Mewis, R.E., 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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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:
NumberType
10.3390/M963DOI
M963Publisher 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
Depositing User: Jonathan Gallacher
Date Added: 04 Dec 2017 15:35
Last Modified: 04 Dec 2017 15:35
URI: http://irep.ntu.ac.uk/id/eprint/32127

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