Enantiomeric NMR signal separation behavior and mechanism of samarium(III) and neodymium(III) complexes with (S ,S )-ethylenediamine-N ,N '-disuccinate

Autor:	Sen-ichi Aizawa, Masaru Okano, Takahiro Kidani
Rok vydání:	2017
Předmět:	Lanthanide Magnetic Resonance Spectroscopy Analytical chemistry chemistry.chemical_element Ethylenediamine Ligands 010402 general chemistry 01 natural sciences Neodymium Catalysis Analytical Chemistry Adduct chemistry.chemical_compound Drug Discovery Organometallic Compounds Spectroscopy Pharmacology Samarium 010405 organic chemistry Chemical shift Organic Chemistry Stereoisomerism Carbon-13 NMR Ethylenediamines 0104 chemical sciences chemistry Stability constants of complexes Physical chemistry
Zdroj:	Chirality. 29:273-281
ISSN:	0899-0042
DOI:	10.1002/chir.22681
Popis:	Enantiomeric 1 H and 13 C NMR signal separation behaviors of various α-amino acids and DL-tartarate were investigated by using the samarium(III) and neodymium(III) complexes with (S,S)-ethylenediamine-N,N'-disuccinate as chiral shift reagents. A relatively smaller concentration ratio of the lanthanide(III) complex to substrates was suitable for the neodymium(III) complex compared with the samarium(III) one, striking a balance between relatively greater signal separation and broadening. To clarify the difference in the signal separation behavior, the chemical shifts of β-protons for fully bound D- and L-alanine (δb (D) and δb (L)) and their adduct formation constants (Ks) were obtained for both metal complexes. Preference for D-alanine was similarly observed for both complexes, while it was revealed that the difference between the δb (D) and δb (L) values is the significant factor to determine the enantiomeric signal separation. The neodymium(III) and samarium(III) complexes can be used complementarily for higher and smaller concentration ranges of substrates, respectively, because the neodymium(III) complex gives the larger difference between the δb (D) and δb (L) values with greater signal broadening compared to the samarium(III) complex.
Databáze:	OpenAIRE
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