Synthesis and Study of the Crystal Structure of 2-[(Dipyrrolidin-1-yl) methylene] malononitrile

Wedad M.  Al-Adiwish; Wedad M. Barag; Mariam S. Saleh

doi:10.54172/mjsc.v37i2.383

Authors

Wedad M. Al-Adiwish Department of Chemistry, Faculty of Science, Zawia University, Libya
Wedad M. Barag Department of Chemistry, Faculty of Science, Zawia University, Libya
Mariam S. Saleh Department of Chemistry, Faculty of Science, Zawia University, Libya

DOI:

https://doi.org/10.54172/mjsc.v37i2.383

Keywords:

single-crystal X-ray study, crystal structure, orthorhombic crystal system, direct displacement, R factor = 0.040, wR = 0.110

Abstract

This study aims to synthesis 2-[(dipyrrolidin-1-yl)methylene] malononitrile 2 and identify its crystal structure by X-ray diffraction analysis. 2-[(dipyrrolidin-1-yl)methylene] malononitrile was prepared by a direct displacement of the methylthio group (SMe) in the 2-[bis(methylthio)methylene] malononitrile 1 with pyrrolidine as cyclic secondary amine by conjugating addition-elimination reaction under reflux conditions for two hours. The compound was obtained in high yield (80%). The structure of compound 2-[(dipyrrolidin-1-yl)methylene] malononitrile2 was identified by performing X-ray diffraction analysis. Suitable crystals of compound 2 were grown by slow evaporation of methanol solution of the compound. The compound 2 crystallized in an orthorhombic crystal system with a space group of Pbcn. In the title compound, the two cyanide groups and the two pyrrolidine rings adopted trans configurations across the C2=C3 bond. The bond lengths and angles of the two pyrrolidinyl rings in the compound are within the normal range. The maximum deviation of N5/C2/C3/C4/N5^a/C4^a is 0.002(1) around C4, and no deviation has been recorded for the fragment N1/N1^a/C2/C3 (0.000 (1)°). The dihedral angle between the pyrrolidine ring and N1/N1^a/C2/C3 is 33.06(8)°, and the dihedral angle between the pyrrolidine ring and N5/C2/C3/C4/N5^a/C4^a is 50.57(7)°. The crystal packing is stabilized by two intermolecular and one intramolecular C---H…N hydrogen bonds, which form a one-dimensional polymeric chain along the axis.

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