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

A Aranburu Leiva; Mandeep Kaur; Sophie Benjamin; Alan M Jones; Stuart Langley; Ryan Mewis

doi:10.3390/M963

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

A Aranburu Leiva, Mandeep Kaur, Sophie Benjamin, Alan M Jones, Stuart Langley, Ryan Mewis

Pharmacy

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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.

Original language	English
Article number	M963
Journal	MolBank
Volume	2017
Issue number	4
Early online date	13 Oct 2017
DOIs	https://doi.org/10.3390/M963
Publication status	E-pub ahead of print - 13 Oct 2017

Keywords

Cyclam
Cyclic voltammetry
Hydrogen-bonding
Macrocycle
X-ray diffraction

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Aranburu_Leiva_et_al_1,8-bis(2-hydroxy)_Molbank_2017
Checked for eligibility: 10/10/2017
Accepted author manuscript, 415 KBLicence: Creative Commons: Attribution (CC BY)
Aranburu-Leiva_et_al_1,8-bis(2-hydroxy-3_Molbank_2017
Checked for eligibility: 08/01/2018
Final published version, 1.04 MBLicence: Creative Commons: Attribution (CC BY)

Cite this

@article{ca55446d653242339860f927f7bfc454,

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

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 = "Cyclam, Cyclic voltammetry, Hydrogen-bonding, Macrocycle, X-ray diffraction",

author = "{Aranburu Leiva}, A and Mandeep Kaur and Sophie Benjamin and Jones, {Alan M} and Stuart Langley and Ryan Mewis",

year = "2017",

month = oct,

day = "13",

doi = "10.3390/M963",

language = "English",

volume = "2017",

journal = "MolBank",

issn = "1422-8599",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "4",

}

TY - JOUR

T1 - 1,8-bis(2-hydroxy-3,5-di-tert-butylbenzyl)-4,11-2 dibenzyl-1,4,8,11-tetraazacyclotetradecane

AU - Aranburu Leiva, A

AU - Kaur, Mandeep

AU - Benjamin, Sophie

AU - Jones, Alan M

AU - Langley, Stuart

AU - Mewis, Ryan

PY - 2017/10/13

Y1 - 2017/10/13

N2 - 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.

AB - 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.

KW - Cyclam

KW - Cyclic voltammetry

KW - Hydrogen-bonding

KW - Macrocycle

KW - X-ray diffraction

U2 - 10.3390/M963

DO - 10.3390/M963

M3 - Article

SN - 1422-8599

VL - 2017

JO - MolBank

JF - MolBank

IS - 4

M1 - M963

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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