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Updated: May 21, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Methanol[1-(methoxymethanimidoyl)-2-(pyridin-2-ylmethyl)guanidine]bis(perchlorato)copper(II)
Atittaya Meenongwa1, Unchulee Chaveerach, Alexander J Blake
1Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand.
Abstract:
The title complex, [Cu(ClO(4))(2)(C(9)H(13)N(5)O)(CH(3)OH)], was synthesized from a methanolysis reaction of N-(methylpyridin-2-yl)cyanoguanidine (L(3)) and copper(II) perchlorate hexahydrate in a 1:1 molar ratio. The Cu(II) ion is six-coordinated by an N(3)O(3) donor set which confers a highly distorted and asymmetric octahedral geometry. Three N-donor atoms from the chelating 1-(methoxymethanimidoyl)-2-(pyridin-2-ylmethyl)guanidine (L(3m)) ligand and one O atom from the methanol molecule define the equatorial plane, with two perchlorate O atoms in the apical sites, one of which has a long Cu-O bond of 2.9074 (19) Å. The dihedral angle between the five- and six-membered chelate rings is 8.21 (8)°. Two molecules are associated into a dimeric unit by intermolecular N-H...O(perchlorate) hydrogen bonds. Additionally, the weakly coordinated perchlorate anions also link adjacent [Cu(ClO(4))(2)(L(3m))(CH(3)OH)] dimers by hydrogen-bonding interactions, resulting in a two-dimensional layer in the (100) plane. Further C-H...O hydrogen bonds link the two-dimensional layers along [100] to generate a three-dimensional network.
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