Abstract
Series of mononuclear complexes of arene Ru and Cp*Rh/Cp*Ir complexes containing (3-picolyl)thiourea derivative ligands, of general formulae [(η6-arene)Ru(L)Cl]Cl and [Cp*M(L)Cl]Cl {L = benzoyl(3-picoylyl)thiourea, arene = benzene (1); p-cymene (2) and M = Rh (3); Ir (4); L = 1,3-bis(3-picolyl)thiourea, arene = benzene (5); p-cymene (6) and M = Rh (7); Ir (8)}, have been synthesized and characterized by spectroscopic methods. X-ray crystallographic studies of complexes (2)–(5), (7), and (8) reveal a typical piano-stool geometry around the metal center with a six-membered metallacycle, in which L acts as an N,S-chelating ligand. Intramolecular N–H···S, S···O, and N–H···N interactions are found to play a significant role in the molecular structures.
Similar content being viewed by others
References
Moriartya Ft M, Gillb US, Kua YY (1988) J Organomet Chem 350:157
Therrien B (2009) Coord Chem Rev 253:493
Carmona D, Lamata MP, Viguri F, Rodriguez R, Lahoz FJ, Dobrinovitch IT, Oro LA (2007) Dalton Trans 38:1911
Thomsen JM, Sheehan SW, Hashmi SM, Campos J, Hintermair U, Crabtree RH, Brudvig GW (2014) J Am Chem Soc 136:13826
Canivet J, Labat G, Evans HS, Fink GS (2005) Eur J Inorg Chem 22:4493
Mishra A, Vajpayee V, Kim H, Lee MH, Jung H, Wang M, Stang PJ, Chi K (2012) Dalton Trans 41:1195
Liu Z, Habtemariam A, Pizarro AM, Fletcher SA, Kisova A, Vrana O, Salassa L, Bruijnincx PCA, Clarkson GJ, Brabec V, Sadler PJ (2011) J Med Chem 54:3011
Fink GS (2010) Dalton Trans 39:1673
Saeed S, Rashid N, Jones PG, Ali M, Hussain R (2010) Eur J Med Chem 45:1323
Rauf MK, Din I, Badshah A, Gielen M, Ebihara M, Vos D, Ahmed S (2009) J Inorg Biochem 103:1135
Solomon VR, Haq W, Smilkstein M, Srivastava K, Puri SK, Katti SB (2010) Eur J Med Chem 45:4990
Li G, Che D, Li Z, Zhu Y, Zou D (2002) New J Chem 26:1629
Henderson W, Nicholson BK, Dinger MB, Bennett RL (2002) Inorg Chim Acta 338:210
Sindhuja E, Ramesh R, Liu Y (2012) Dalton Trans 41:5351
Meier SM, Hanif M, Adhireksan Z, Pichler V, Novak M, Jirkovsky E, Jakupec MA, Arion VB, Davey CA, Keppler BK, Hartinger CG (2013) Chem Sci 4:1837
Lalrempuia R, Rao KM (2003) Polyhedron 22:3155
Perrin DD, Armarego WLF (1996) Purification of laboratory chemicals, 4th edn. Butterworths-Heinemann, London
Bennett MA, Huang TN, Matheson TW, Smith AK (1982) Inorg Synth 21:74
Tonnemann J, Risse J, Grote Z, Scopelliti R, Severin K (2013) Eur J Inorg Chem 26:4558
Kaminsky W, Goldberg KI, West DX (2002) J Mol Struct 605:9
Sheldrick GM (1990) Acta Cryst A 46:467
Win GX, Farrugia LJ (1999) J Appl Crystallogr 32:837
Farrugia LJ (1997) J Appl Cryst 30:565
Bellamy L (1954) Infrared spectra of complex molecules. Methuen, London
Narayana B, Gajendragad MR (1997) Turk J Chem 21:65
Silverstien RM, Bassler GC, Morrill TC (1991) Spectroscopic identification of organic compounds, 5th edn. Wiley, New York
Paul LEH, Furrer J, Therrien B (2013) J Organomet Chem 734:45
Prakash O, Joshi H, Sharma KN, Gupta PL, Singh AK (2014) Organometallics 33:3804
Singh P, Singh AK (2010) Eur J Inorg Chem 29:4187
Rao VA, Pallepogu R, Zhou ZY, Rao KM (2012) Inorg Chim Acta 387:37
Adams M, Li Y, Khot H, De Kock C, Smith PJ, Land K, Chibalea K, Smith GS (2013) Dalton Trans 42:4677
Hohloch S, Hettmanczyk L, Sarkar B (2014) Eur J Inorg Chem 33:3164
Desiraju GR, Steiner T (2001) The weak hydrogen bond: in structural chemistry and biology. Oxford University Press, New York
Cheng B, Tehrani AA, Hu ML, Morsali A (2014) CrystEngComm 16:9125
Iwaoka M, Isozumi N (2012) Molecules 17:7266
Du P, Jiang XK, Li ZT (2009) Tetrahedron Lett 50:320
Filak LK, Goschl S, Heffeter P, Samper KG, Egger AE, Jakupec MA, Keppler BK, Berger W, Arion VB (2013) Organometallics 32:903
Bacchi A, Cantoni G, Granelli M, Mazza S, Pelagatti P, Rispoli G (2011) Cryst Growth Des 11:5039
Danovich D, Shaik S, Neese F, Echeverría J, Aullón G, Alvarez S (2013) J Chem Theory Comput 9:1977
Acknowledgments
Mahesh K thanks UGC, New Delhi, for providing financial assistance in the form of University Fellowship (UGC-RFSMS). We thank DST-PURSE SCXRD and SAIF of NEHU for providing X-ray analysis and facility to spectral study.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kalidasan, M., Nagarajaprakash, R. & Rao, K.M. Synthesis and molecular studies of half-sandwich arene ruthenium and Cp*Rh/Cp*Ir complexes containing (3-picolyl)thiourea derivatives as N,S-bidentate donor ligands. Transition Met Chem 40, 531–539 (2015). https://doi.org/10.1007/s11243-015-9946-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11243-015-9946-x