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Paper | Special issue | Vol 30, No. 2, 1990, pp.1079-1090
Published online, 1st January, 1970
DOI: 10.3987/COM-89-SR008
Synthesis and Crystal Structure of Hydrogen-bonded Long-Chain of 1:1-Methanol:1-[N-Methylpyridoxylidenium]-2-[21-pyridyl]hydrazine Iodide

Schelly Avramovici-Grisaru, Shmuel Cohen, and Shalom Sarel*

*Department of Medicinal Chemistry, The Hebrew University, P.O. Box 12065, Jerusalem 91120, Israel


The synthesis and N-monomehtylation [(5)→(6a)] of 1-[pyridoxylidene]-2-[21-pyridyl]hydrazine (5) are herein described. The product, 1-[N-methylpyridoxylidenium]-2-21-pyridyl]hydrazine iodide (6a), on recrystallization from methanol yielded hydrogen-bonded long-chains of 1:1-methanol: (6a) of crystal structure (8) [Figure 2]. The reaction of (6a) with aqueous HClO4 afforded dimers of the corresponding diperchlorate of structure (6b) [Figure 1]. The formation of (8) is rationalized in terms of cooperative hydrogen-bonding, arising from the ability of the alcoholic OH group to function both as acceptor and donor. The dimeric crystal structure of (6b) is envisioned to arise from an alternative mode of H-bonding, namely, the "three- center" geometry, influenced by the ClO4 oxygen acceptors.