Palladium(II) complexes with R(2)edda derived ligands. Part I. Reaction of diisopropyl (S,S)-2,2 '-(1,2-ethanediyldiimino)-dipropanoate with K-2[PdCl4]
Kompleksi paladijuma(II) sa ligandima R2edda tipa, deo I - reakcija diizopropil-(S,S)-2,2'-(1,2-etandiildiimino)dipropanoata sa K2[PdCl4]
2009
Authors
Krajcinovic, Bojana B.Kaluđerović, Goran N.
Steinborn, Dirk
Schmidt, Harry
Wagner, Christoph
Merzweiler, Kurt
Trifunović, Srećko R.
Sabo, Tibor
Article (Published version)
Metadata
Show full item recordAbstract
The reaction of K-2[PdCl4] with (S,S)-(i-Pr)(2)eddip diester (diisopropyl (S,S)-2,2'-(1,2-ethanediyldiimino)dipropanoate) resulted in {PdCl2[(S,S)-(i-Pr)-Pr)(2)eddip-kappa N-2,N']} (1) and {PdCl[(S,S)-(i-Pr)eddip-kappa N-2,N',kappa O]} (2) with one hydrolyzed ester group. The compounds were characterized by spectroscopic methods and it was proved that the reaction is diastereoselective (H-1- and C-13-NMR) in the case of 2 (one diastereoisomer of four possible). The structure of 2 was determined by X-ray diffraction analysis, indicating that the product is the (R,R)-N,N' configured isomer. In contrast, the reaction yielding 1 produced two of three possible diastereoisomers. DFT calculations support the formation of two diastereoisomers of I and of one diastereoisomer of 2.
U reakciji K2[PdCl4] sa (S,S)-(i-Pr)2eddip diestrom [diizopropil-(S,S)-2,2'-(1,2-etandi-ildiimino)dipropanoat] dobijaju se {PdCl2[(S,S)-(i-Pr)2eddip-κ2N,N']} (1) i {PdCl[(S,S)-(i-Pr)eddip-κ2N,N',κO]} (2) sa jednom hidrolizovanom estarskom grupom. Jedinjenja su okarakterisana spektroskopskim metodama i dokazano je da je ova reakcija dijastereoselektivna (1H- i 13C-NMR) u slučaju 2 (jedan dijastereoizomer od moguća četiri). Struktura jedinjenja 2 je određena rendgenskom strukturnom analizom i nađeno je da je dobijeni proizvod (R,R)-N,N' izomer. Suprotno tome, u slučaju jedinjenja 1 dobijeni proizvod je smeša dva od tri moguća dijastereoizomera. DFT proračuni potvrđuju formiranje dva dijastereoizomera jedinjenja 1 i jednog dijastereoizomera jedinjenja 2.
Keywords:
palladium complexes / crystal structure / crystal structure / EDDP ligands / EDDP ligands / DFT calculations / DFT calculationsSource:
Journal of the Serbian Chemical Society, 2009, 74, 4, 389-400Publisher:
- Serbian Chemical Soc, Belgrade
Funding / projects:
- Synthesis, characterization and activity of organic and coordination composition and their application in (bio) nanotechnology (RS-MESTD-MPN2006-2010-142010)
- Struktura novih kompleksa jona prelaznih metala i mehanizam njihovih reakcija sa biološki značajnim ligandima (RS-MESTD-MPN2006-2010-142008)
- Alexander von Humboldt Foundation
DOI: 10.2298/JSC0904389K
ISSN: 0352-5139
WoS: 000266210200004
Scopus: 2-s2.0-68949178838
Collections
Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Krajcinovic, Bojana B. AU - Kaluđerović, Goran N. AU - Steinborn, Dirk AU - Schmidt, Harry AU - Wagner, Christoph AU - Merzweiler, Kurt AU - Trifunović, Srećko R. AU - Sabo, Tibor PY - 2009 UR - https://cherry.chem.bg.ac.rs/handle/123456789/989 AB - The reaction of K-2[PdCl4] with (S,S)-(i-Pr)(2)eddip diester (diisopropyl (S,S)-2,2'-(1,2-ethanediyldiimino)dipropanoate) resulted in {PdCl2[(S,S)-(i-Pr)-Pr)(2)eddip-kappa N-2,N']} (1) and {PdCl[(S,S)-(i-Pr)eddip-kappa N-2,N',kappa O]} (2) with one hydrolyzed ester group. The compounds were characterized by spectroscopic methods and it was proved that the reaction is diastereoselective (H-1- and C-13-NMR) in the case of 2 (one diastereoisomer of four possible). The structure of 2 was determined by X-ray diffraction analysis, indicating that the product is the (R,R)-N,N' configured isomer. In contrast, the reaction yielding 1 produced two of three possible diastereoisomers. DFT calculations support the formation of two diastereoisomers of I and of one diastereoisomer of 2. AB - U reakciji K2[PdCl4] sa (S,S)-(i-Pr)2eddip diestrom [diizopropil-(S,S)-2,2'-(1,2-etandi-ildiimino)dipropanoat] dobijaju se {PdCl2[(S,S)-(i-Pr)2eddip-κ2N,N']} (1) i {PdCl[(S,S)-(i-Pr)eddip-κ2N,N',κO]} (2) sa jednom hidrolizovanom estarskom grupom. Jedinjenja su okarakterisana spektroskopskim metodama i dokazano je da je ova reakcija dijastereoselektivna (1H- i 13C-NMR) u slučaju 2 (jedan dijastereoizomer od moguća četiri). Struktura jedinjenja 2 je određena rendgenskom strukturnom analizom i nađeno je da je dobijeni proizvod (R,R)-N,N' izomer. Suprotno tome, u slučaju jedinjenja 1 dobijeni proizvod je smeša dva od tri moguća dijastereoizomera. DFT proračuni potvrđuju formiranje dva dijastereoizomera jedinjenja 1 i jednog dijastereoizomera jedinjenja 2. PB - Serbian Chemical Soc, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Palladium(II) complexes with R(2)edda derived ligands. Part I. Reaction of diisopropyl (S,S)-2,2 '-(1,2-ethanediyldiimino)-dipropanoate with K-2[PdCl4] T1 - Kompleksi paladijuma(II) sa ligandima R2edda tipa, deo I - reakcija diizopropil-(S,S)-2,2'-(1,2-etandiildiimino)dipropanoata sa K2[PdCl4] VL - 74 IS - 4 SP - 389 EP - 400 DO - 10.2298/JSC0904389K ER -
@article{ author = "Krajcinovic, Bojana B. and Kaluđerović, Goran N. and Steinborn, Dirk and Schmidt, Harry and Wagner, Christoph and Merzweiler, Kurt and Trifunović, Srećko R. and Sabo, Tibor", year = "2009", abstract = "The reaction of K-2[PdCl4] with (S,S)-(i-Pr)(2)eddip diester (diisopropyl (S,S)-2,2'-(1,2-ethanediyldiimino)dipropanoate) resulted in {PdCl2[(S,S)-(i-Pr)-Pr)(2)eddip-kappa N-2,N']} (1) and {PdCl[(S,S)-(i-Pr)eddip-kappa N-2,N',kappa O]} (2) with one hydrolyzed ester group. The compounds were characterized by spectroscopic methods and it was proved that the reaction is diastereoselective (H-1- and C-13-NMR) in the case of 2 (one diastereoisomer of four possible). The structure of 2 was determined by X-ray diffraction analysis, indicating that the product is the (R,R)-N,N' configured isomer. In contrast, the reaction yielding 1 produced two of three possible diastereoisomers. DFT calculations support the formation of two diastereoisomers of I and of one diastereoisomer of 2., U reakciji K2[PdCl4] sa (S,S)-(i-Pr)2eddip diestrom [diizopropil-(S,S)-2,2'-(1,2-etandi-ildiimino)dipropanoat] dobijaju se {PdCl2[(S,S)-(i-Pr)2eddip-κ2N,N']} (1) i {PdCl[(S,S)-(i-Pr)eddip-κ2N,N',κO]} (2) sa jednom hidrolizovanom estarskom grupom. Jedinjenja su okarakterisana spektroskopskim metodama i dokazano je da je ova reakcija dijastereoselektivna (1H- i 13C-NMR) u slučaju 2 (jedan dijastereoizomer od moguća četiri). Struktura jedinjenja 2 je određena rendgenskom strukturnom analizom i nađeno je da je dobijeni proizvod (R,R)-N,N' izomer. Suprotno tome, u slučaju jedinjenja 1 dobijeni proizvod je smeša dva od tri moguća dijastereoizomera. DFT proračuni potvrđuju formiranje dva dijastereoizomera jedinjenja 1 i jednog dijastereoizomera jedinjenja 2.", publisher = "Serbian Chemical Soc, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Palladium(II) complexes with R(2)edda derived ligands. Part I. Reaction of diisopropyl (S,S)-2,2 '-(1,2-ethanediyldiimino)-dipropanoate with K-2[PdCl4], Kompleksi paladijuma(II) sa ligandima R2edda tipa, deo I - reakcija diizopropil-(S,S)-2,2'-(1,2-etandiildiimino)dipropanoata sa K2[PdCl4]", volume = "74", number = "4", pages = "389-400", doi = "10.2298/JSC0904389K" }
Krajcinovic, B. B., Kaluđerović, G. N., Steinborn, D., Schmidt, H., Wagner, C., Merzweiler, K., Trifunović, S. R.,& Sabo, T.. (2009). Palladium(II) complexes with R(2)edda derived ligands. Part I. Reaction of diisopropyl (S,S)-2,2 '-(1,2-ethanediyldiimino)-dipropanoate with K-2[PdCl4]. in Journal of the Serbian Chemical Society Serbian Chemical Soc, Belgrade., 74(4), 389-400. https://doi.org/10.2298/JSC0904389K
Krajcinovic BB, Kaluđerović GN, Steinborn D, Schmidt H, Wagner C, Merzweiler K, Trifunović SR, Sabo T. Palladium(II) complexes with R(2)edda derived ligands. Part I. Reaction of diisopropyl (S,S)-2,2 '-(1,2-ethanediyldiimino)-dipropanoate with K-2[PdCl4]. in Journal of the Serbian Chemical Society. 2009;74(4):389-400. doi:10.2298/JSC0904389K .
Krajcinovic, Bojana B., Kaluđerović, Goran N., Steinborn, Dirk, Schmidt, Harry, Wagner, Christoph, Merzweiler, Kurt, Trifunović, Srećko R., Sabo, Tibor, "Palladium(II) complexes with R(2)edda derived ligands. Part I. Reaction of diisopropyl (S,S)-2,2 '-(1,2-ethanediyldiimino)-dipropanoate with K-2[PdCl4]" in Journal of the Serbian Chemical Society, 74, no. 4 (2009):389-400, https://doi.org/10.2298/JSC0904389K . .