In order to increase the organic solvent solubility of aryl-hydrazones, N-alkylation was attempted. The substrates acetaldehyde 2,46-trinitrophenylhydrazone (acetaldehyde TNP) and acetone 2,46-trinitrophenylhydrazone (acetone TNP) were prepared and characterized. Alkylation attempts were made with reagents and conditions the same as those successful in alkylating acetone 2,4-dinitrophenylhydrazone (acetone DNP). Attempts were made with differing alkylating reagents, equivalence ratios, times and temperatures. Alkylating procedes via the anion of the substrate. The anions of the substrate were prepared and characterized via uv and nmr. Altered structure of the anion relative to the hydrazone lead to its chemical stability and appeared to preclude its alkylation. Mass spectral analysis and simple HMO calculation were attempted to further characterize the TNP's and their anions. Extensive analysis of the isomers of the TNP's by nmr was accomplished. The anions of the TNP's were studied via nmr using high temperatures, basic solutions and contributed substantively to the proposed anionic structure.
Library of Congress Subject Headings
Alkylation; Chemical reactions
Department, Program, or Center
School of Chemistry and Materials Science (COS)
Bayley, Ann, "Alkylation and arylalkylation of hydrazones" (1971). Thesis. Rochester Institute of Technology. Accessed from
RIT – Main Campus