Jump to main content
Jump to site search

Issue 7, 2009
Previous Article Next Article

Co-crystallization experiments of thiocarbamides with bipyridine-type molecules

Author affiliations


Co-crystallization experiments conducted between thiocarbamide derivatives, (E)-O-alkyl N-aryl-thiocarbamide, ROC([double bond, length as m-dash]S)N(H)R′, for R = Me, Et and iPr, and R′ = Ph and PhNO2-4, containing a pharmaceutically active chromophorei.e. –C([double bond, length as m-dash]S)–N(H)–, and the bipyridine-type molecules, 4,4′-bipyridine, trans-1,2-bis(4-pyridyl)ethene and 1,2-bis(4-pyridyl)ethane, showed the formation of stable 2 : 1 co-crystals, i.e. {[ROC([double bond, length as m-dash]S)N(H)R′]2(bipyridine-type molecule)}. Novel species were formed by grinding and solvent drop grinding methods, and characterized by powder X-ray diffraction. Five 2 : 1 co-crystals were isolated as single crystals by slow evaporation methods and fully characterized by spectroscopic and X-ray crystallographic methods. Uniformly, trimeric aggregates were formed where each pyridine-nitrogen was connected to an amide-H via a Npyridine⋯H–Namide hydrogen bond. This study shows that the eight-membered {⋯H–N–C[double bond, length as m-dash]S}2 homosynthon found in the parent thiocarbamides is readily disrupted in the presence of bipyridine-type molecules to enable the formation of the stable heterosynthon, {N⋯H–N}.

Graphical abstract: Co-crystallization experiments of thiocarbamides with bipyridine-type molecules

Back to tab navigation

Supplementary files

Publication details

The article was received on 15 Dec 2008, accepted on 23 Feb 2009 and first published on 17 Mar 2009

Article type: Paper
DOI: 10.1039/B822555A
Citation: CrystEngComm, 2009,11, 1352-1361
  •   Request permissions

    Co-crystallization experiments of thiocarbamides with bipyridine-type molecules

    C. A. Ellis, M. A. Miller, J. Spencer, J. Zukerman-Schpector and E. R. T. Tiekink, CrystEngComm, 2009, 11, 1352
    DOI: 10.1039/B822555A

Search articles by author