Synthesis and reactivity of new water soluble carbodiimides

M. N. Gertzuk, V. N. Sergeev, A. V. Tsytovich, N. G. Dolinnaya, V. P. Kuchar

Institute of Bioorganic Chemistry, Acidemy of Sciences of the Ukrainian SSR , Kiev; Department of Chemistry, M. V. Lomonosov Moscow State University

Abstract: A series of new water soluble carbodiimides have been synthesized, their ability for ring-chain tautomerism being studied by IR spectroscopy. The rate constants of hydrolysis of the carbodiimides in the presence and in the absence of a phosphate donor, mononucleotide, have been measured. It is shown that intramolecular cyclyzation of carbodiimides inhibits their interaction with nucleophiles. For example the compound RN=C=NCH2CH2NH(CH3)2C1, forming a five-membered ring, is practically inert in the presence of nucleophiles.

Russian Journal of Bioorganic Chemistry 1990, 16 (9):1268-1276

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