Abstract
Two new ligands, having flexible coordination ability, 1,5-bis(quinoline-2-carbaldehyde) thiocarbohydrazone and 1,5-bis(quinoline-2-carbaldehyde) carbohydrazone were synthesized and characterized by elemental analysis, IR, and UV spectral studies. The compounds exist in the thione/ketone tautomeric forms, as evidenced by IR spectral data. The structure of bis(quinoline-2-aldehyde) thiocarbohydrazone has been solved by single crystal XRD study. The compound C21H16N6S crystallizes in triclinic form with two independent molecules in the asymmetric unit, space group \( {\text{P}}\overline 1\), Z = 4, V = 1856.1(6) Å3 with unit cell parameters a = 11.331(2) Å, b = 11.714(2) Å, c = 15.116(3) Å, α = 100.369(4)°, β = 109.512(4)° and γ = 90.134(4)°. Both molecules exist in the thione forms and show a Z–Z configuration about both azomethine bonds, with quinoline nitrogens on opposite sides. The N–N, N–C and the C–S bond distances of the thiocarbohydrazide moiety suggest extensive electron delocalization of the whole thiocarbohydrazone moiety.
Index Abstract
Synthesis and spectral studies of bisthiocarbohydrazone and biscarbohydrazone of quinoline-2-carbaldehyde: Crystal structure of bis(quinoline-2-aldehyde) thiocarbohydrazone, E. Manoj, M. R. Prathapachandra Kurup, E. Suresh. Bis(quinoline-2-aldehyde) thiocarbohydrazone crystallizes in the tricliniccrystal system with two independent molecules in the asymmetric unit, and exists in the thione tautomeric form. Both molecules show a Z-Z configuration about both azomethinebonds, with quinoline nitrogens on opposite sides. The N–N, N–C and the C–S bond distances of the thiocarbohydrazide moiety suggest extensive electron delocalization of the whole thiocarbohydrazone moiety
.
Similar content being viewed by others
References
Manoj E, Kurup MRP, Fun H-K (2007) Inorg Chem Commun 10:324
Bacchi A, Bonini A, Carcelli M, Farraro FJ (1996) Chem Soc Dalton Trans 2699
Moubaraki B, Murray KS, Ranford JD, Vittal JJ, Wang X, Xu YJ (1999) Chem Soc Dalton Trans 3573
Bustos GR, Burdkhardt O, Schrebler R, Carrilo D (1990) Inorg Chem 29:3996
Abu-Hussen AAA, Emara AAA (2004) J Coord Chem 57:973
Bacchi A, Carcelli M, Pelagatti P, Pelizzi C, Pelizzi G, Zani FJ (1999) Inorg Biochem 75:123
Blumenkopf TA, Harrington JA, Kolbe CS, Bankston DD, Morrison RW, Bigham EC, Styles VL, Spector T (1992) J Med Chem 35:306
Spector T, Harrington JA, Morrison RW Jr, Lambe CU, Nelson DJ, Averett DR, Biron K, Furman PA (1989) Proc Natl Acad Sci USA 86:1051
He C, Duan C-y, Fang C-j, Liu Y-j, Meng Q-j (2000) J Chem Soc Dalton Trans 1207
Manoj E, Kurup MRP, Fun H-K, Chantrapromma S (2005) Acta Cryst E61:o4110
Manoj E, Kurup MRP, Fun H-K, Punnoose A (2007) Polyhedron 26:4451
Lin Z, Chen H, Zhuang J, Wu Y, Lin YJ (1998) Incl Phen and Mol Recog Chem 30:13
Siemens, SMART and SAINT (1996) Area Detector Control and Integration Software, Siemens Analytical X-ray Instruments Inc. Madison, Wisconsin, USA
Sheldrick GM (1997) SHELXTL Version 5.1, Software Reference Manual, Bruker AXS Inc, Madison, Wisconsin, USA
Farrugia LJ (1997) J Appl Cryst 30:565
Spek AL (1990) Acta Cryst A46:C-34
Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M, van de Streek J (2006) J Appl Cryst 39:453
Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor R (1987) J Chem Soc Perkin Trans 2:S1
Chantrapromma S, Razak IA, Fun H-K, Karalai C, Zhang H, Xie F-X, Tian Y-P, Ma W, Zhang Y-H, Ni S-S (2001) Acta Cryst C.57:289
Benson SW (1965) J Chem Educ 42:502
Acknowledgement
E. Manoj thanks the University Grants Commission, New Delhi, India for financial support in the form of fellowship.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Manoj, E., Kurup, M.R.P. & Suresh, E. Synthesis and Spectral Studies of Bisthiocarbohydrazone and Biscarbohydrazone of Quinoline-2-carbaldehyde: Crystal Structure of Bis(quinoline-2-aldehyde) Thiocarbohydrazone. J Chem Crystallogr 38, 157–161 (2008). https://doi.org/10.1007/s10870-007-9267-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10870-007-9267-9