Structure of a new Schiff base of gossypol with 1-(3-aminopropyl)-2-pyrrolidinone studied by the X-ray, FT-IR, NMR, ESI-MS and PM5 methods

摘要: Abstract Crystals of the Schiff base derivative gossypol with 1-(3-aminopropyl)-2-pyrrolidinone (GSPP) have been obtained and examined by X-ray diffraction, FT-IR, 1H 13C NMR methods. The crystallizes in ethanol solution as an inclusion compound H2O molecules. crystal space group is P21/n a = 7.5555(5), b = 18.7583(12), c = 29.415(2) A, β = 94.270(6)°, Z = 4. In exists enamine–enamine tautomeric form. This form also conserved chloroform solution. Water molecules are enclosed hydrophilic channels where they hydrogen-bonded to pyrrolidinone moieties O5H groups base. FT-IR spectral features agreement data indicating different bonding arrangement moieties. spectrum GSPP implies structural equivalence these two groups. ESI-MS studies mixtures formic acid demonstrated formation mono- di-protonated species. PM5 semiempirical calculations allow visualization most energetically favourable structures protonated