6533b85efe1ef96bd12c0862

RESEARCH PRODUCT

Alkyl and diether bridged N,N,N′,N′-tetra(2-hydroxybenzyl)diamines: effects of hydrogen bonding on structure and solubility

Antti RiisiöMikko M. HänninenReijo Sillanpää

subject

chemistry.chemical_classificationbiologyChemistryHydrogen bondGeneral ChemistryCondensed Matter Physicsbiology.organism_classificationMedicinal chemistryCrystalOrganic chemistryMoleculeTetralipids (amino acids peptides and proteins)General Materials ScienceSolubilitySpectroscopyta116Single crystalAlkyl

description

A solvent-free one-step method has been used to prepare two N,N,N′,N′-tetra(2-hydroxy-3,5-dimethylbenzyl)diaminoalkanes containing a long n-alkyl bridge (6 and 8 CH2 groups between N-atoms). In addition, three novel N,N,N′,N′-tetra(2-hydroxy-5-alkyl-3-alkylbenzyl)-diaminoalkane-ethers (alkyl = methyl or t-butyl) have been prepared using the same method. The compounds were studied in the solid state using single crystal X-ray diffraction and their solubility was studied using UV/Vis spectroscopy. In the solid state, hydrogen bonding plays a key role in controlling the crystal packing and conformations of the molecules, thus affecting the solubility and properties of the compounds.

https://doi.org/10.1039/c2ce26027a