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Volume 2017
Issue 4
10.3390/M963
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Short Note

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

by
Ane I. Aranburu Leiva
1,
Mandeep Kaur
1,
Sophie L. Benjamin
2,
Alan M. Jones
3,
Stuart K. Langley
1 and
Ryan E. Mewis
1,*
1
School of Science and the Environment, Division of Chemistry and Environmental Science, Manchester Metropolitan University, John Dalton Building, Chester St., Manchester M1 5GD, UK
2
School of Science and Technology, Nottingham Trent University, Nottingham NG11 8NS, UK
3
School of Pharmacy, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK
*
Author to whom correspondence should be addressed.
Molbank 2017, 2017(4), M963; https://doi.org/10.3390/M963
Submission received: 15 September 2017 / Revised: 9 October 2017 / Accepted: 11 October 2017 / Published: 13 October 2017
(This article belongs to the Section Structure Determination)
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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.
Keywords: macrocycle; cyclam; cyclic voltammetry; X-ray diffraction; hydrogen-bonding macrocycle; cyclam; cyclic voltammetry; X-ray diffraction; hydrogen-bonding
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MDPI and ACS Style

Aranburu Leiva, A.I.; Kaur, M.; Benjamin, S.L.; Jones, A.M.; Langley, S.K.; Mewis, R.E. 1,8-bis(2-hydroxy-3,5-di-tert-butylbenzyl)-4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane. Molbank 2017, 2017, M963. https://doi.org/10.3390/M963

AMA Style

Aranburu Leiva AI, Kaur M, Benjamin SL, Jones AM, Langley SK, Mewis RE. 1,8-bis(2-hydroxy-3,5-di-tert-butylbenzyl)-4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane. Molbank. 2017; 2017(4):M963. https://doi.org/10.3390/M963

Chicago/Turabian Style

Aranburu Leiva, Ane I., Mandeep Kaur, Sophie L. Benjamin, Alan M. Jones, Stuart K. Langley, and Ryan E. Mewis. 2017. "1,8-bis(2-hydroxy-3,5-di-tert-butylbenzyl)-4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane" Molbank 2017, no. 4: M963. https://doi.org/10.3390/M963

APA Style

Aranburu Leiva, A. I., Kaur, M., Benjamin, S. L., Jones, A. M., Langley, S. K., & 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. https://doi.org/10.3390/M963

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