Tris(triazolyl)borate ligands of intermediate steric bulk for the synthesis of biomimetic structures with hydrogen bonding and solubility in hydrophilic solvents.
Tris(triazolyl)borate ligands (Ttz) of intermediate steric bulk were synthesized to investigate their potential for hydrogen bonding and improved solubility in hydrophilic solvents as applied to biomimetic chemistry. The crystal structure of 3-phenyl-5-methyl-1,2,4-triazole (Htz(Ph,Me)) revealed hydrogen bonding and pi stacking interactions. The new ligand salt, potassium tris(3-phenyl-5-methyl-1,2,4-triazolyl)borate (KTtz(Ph,Me)) was synthesized as the first example of a Ttz ligand of intermediate steric bulk. Metathesis between KTtz(Ph,Me) and NaCl followed by recrystallization produced [NaTtz(Ph,Me)].6CH3OH in which the geometry around the sodium is octahedral with an unusual N(3)O(3) donor set; this structure also shows that a hydrogen bonding network is formed by methanol molecules and triazole nitrogens. (Ttz(Ph,Me))ZnCl was synthesized and characterized crystallographically as [(Ttz(Ph,Me))ZnCl].0.5CH3OH in which the zinc is tetrahedral and the triazole rings are within hydrogen bonding distance of CH(3)OH. All of these new compounds are methanol soluble to varying degrees and Htz(Ph,Me) and KTtz(Ph,Me) are soluble in methanol/water mixtures.
Department of Chemistry, Drexel University, 3141 Chestnut Street, Philadelphia, PA 19104, USA.
Sean R
SR
Gardner
Elizabeth T
ET
Papish
Wesley H
WH
Monillas
Glenn P A
GP
Yap
D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry; D001881:Borates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008024:Ligands; D012995:Solubility; D012997:Solvents / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*; D017967:Zinc Compounds / Q000737:chemistry / Q000378:metabolism*
D001881:Borates; D008024:Ligands; D012997:Solvents; D014230:Triazoles; D017967:Zinc Compounds