title: Importance of ortho proton donors in catalysis of hydrazone formation.
abstract: Anthranilic acids were recently reported as superior catalysts for hydrazone and oxime formation compared to aniline, the classic catalyst for these reactions. Here, alternative proton donors were examined with varied pKa in an effort to enhance activity at biological pH. The experiments show that 2-aminobenzenephosphonic acids are superior to anthranilic acids in catalyzing hydrazone formation with common aldehyde substrates.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States.
authors.forename: Pete
authors.initials: P
authors.lastname: Crisalli
authors.forename: Eric T
authors.initials: ET
authors.lastname: Kool
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry; D002384:Catalysis; D006835:Hydrazones / Q000138:chemical synthesis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D015394:Molecular Structure; D010091:Oximes / Q000138:chemical synthesis; D011522:Protons; D062367:ortho-Aminobenzoates / Q000737:chemistry
chemical_list: D000814:Aniline Compounds; D006835:Hydrazones; D010091:Oximes; D011522:Protons; D062367:ortho-Aminobenzoates