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RESEARCH ARTICLE (Open Access)
Contents Vol 75(7)

Compounds of amine-substituted cyclic amines: synthesis and structures

Neil F. Curtis https://orcid.org/0000-0002-1074-0999 A *
+ Author Affiliations
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A School of Chemical and Physical Sciences, Victoria University of Wellington, Box 600, Wellington 6140, New Zealand.




Neil Curtis was born in Auckland, New Zealand in 1931. He attended Auckland University, graduating with a PhD in Chemistry in 1955. After spending 2 years with (not yet Sir) Ron Nyholm in London, studying rhenium diarsine compounds, he was appointed as a lecturer at the Victoria University of Wellington. During his PhD studies he had been visited by the Princes of Serandip, who persuaded him to recrystallise some nickel(ii) ethanediamine compounds from acetone, which resulted in unexpected products with unusual and intriguing properties. In Wellington he resumed study of these compounds, eventually establishing that they had aza-macrocyclic ligand structures, reported in 1961. This started an extensive flurry of research into aza-macrocyclic ligand coordination chemistry. Much of Neil’s subsequent research has involved extensions of these reactions. During a period of sabbatical leave at MIT with Al Cotton in 1964 he returned to rhenium chemistry and was in the group reporting the rhenium–rhenium quadruple bond. During a later leave period with Alan Sargeson at ANU he developed new methods of synthesis of azamacrocycle ligand compounds, including those described in this Review. Neil has remained at the Victoria University of Wellington for his academic career. He was appointed as Professor of Chemistry in 1975, and after retiring in 1996 as Emeritus Professor of Chemistry. Neil was awarded a Fellowship of the Royal Society of New Zealand in 1975 and served on the Council of the Society in various roles, from 1982 to 1994, including terms as Hon. Treasurer and Vice-President. Neil has 45 publications in the Australian Journal of Chemistry and was included in the Journal’s list of ‘golden oldies of inorganic chemistry’, Aust. J. Chem., 1995, 48, 689. Goodness knows what that makes him now!
* Correspondence to: neil.curtis@vuw.ac.nz

Handling Editor: Paul V. Bernhardt

Australian Journal of Chemistry 75(7) 439-466 https://doi.org/10.1071/CH22020
Submitted: 26 January 2022  Accepted: 12 April 2022   Published: 8 August 2022

© 2022 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND)

Abstract

Cyclic tetra-amines with amine substituents on the central carbon atom of C3 ring segments are readily prepared by reduction of nitro-substituted aza-macrocycles, formed by reactions of metal-ion amine compounds with formaldehyde and a nitro-alkane. Reactions of bis-(ethane-1,2-diamine)-copper(ii) or -nickel(ii) cations with formaldehyde and nitroethane form the trans (anti) and cis (syn) isomers of (6,13-dimethyl-6,13-di-nitro-1,4,8,11-tetra-azacyclotetradecane)-copper(ii) or -nickel(ii)) cations, which are readily reduced to form the trans and cis-6,13-diamino cations, from which the trans- and cis-amine substituted cyclic tetra-amines can be isolated. Similar reactions for the (3,7-diaza-nonane-1,9-diamine)-copper(ii) or -nickel(ii) cations lead to 6-methyl-1,4,8,11-tetra-azacyclotetradecane-6-amine. Amine-substituted cyclic tetra-amines with different ring sizes or alkyl substituents can similarly be prepared by using different diamines or alkyl-nitro compounds. This review is primarily about compounds formed by trans-6,13-diamino and 6-amino-1,4,8,11-tetraazacyclotetradecanes with d-transition-metal ions. The amines react with transition-metal ions in much the same manner as 1,4,8,11-tetraazacyclotetradecane (cyclam), forming compounds with isomeric configurations arising from the four chiral nitrogen centres of coordinated cyclam, the cis- or trans-configurations of the amine substituents and a form of geometrical isomerism arising from the relationship between the chiral coordinated cyclam configuration and the orientation of the substituents. The amine-substituted cyclams coordinate by the four cyclam nitrogen atoms, in planar or folded arrangements, and also by one or both of the amine substituents. Non-coordinated amine substituents can be protonated. The amine substituents can be modified by methylation, amide formation and reaction with aldehydes to form imines. The imines formed with functionalised aldehydes can be reduced to form variously functionalised secondary amine substituents. This all leads to complex coordination chemistry and X-ray crystallographic structure determinations have been critical in understanding the configurations present. Structures in the Cambridge Crystallographic Data Base of all relevant compounds are listed.

Keywords: aldehyde, amine, azamacrocycles, coordinated ligands, coordination compounds, crystal structures, cyclic amines, isomerism, reactions of nitroalkanes.


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