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First direct discrimination of chiral phosphine selenide (P=Se) derivatives by multinuclear magnetic resonance spectroscopy in the presence of a chiral dirhodium complex
Author(s) -
Malik Shahid,
Duddeck Helmut,
Omelanczuk Jan,
Choudhary Muhammad Iqbal
Publication year - 2002
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10105
Subject(s) - chemistry , phosphine , selenide , nuclear magnetic resonance spectroscopy , spectroscopy , resonance (particle physics) , chirality (physics) , nuclear magnetic resonance , crystallography , stereochemistry , organic chemistry , chiral symmetry , catalysis , selenium , atomic physics , physics , quantum mechanics , nambu–jona lasinio model , quark
Enantiomeric ratios of compounds with P=Se functionalities (phosphine selenides) can easily be determined by 1 H, 13 C, 31 P, and 77 Se NMR spectroscopic inspection of their diastereomeric complexes with ( R )‐Rh 2 (MTPA) 4 (MTPA‐H ≡ methoxytrifluoromethylphenylacetic acid; Mosher's acid). This is the first facile and rapid spectroscopic method for chiral recognition in this class of compounds. Whereas most complexation shifts Δδ are moderate or even negligible, significant signal dispersions Δν can be observed. Some rationalization for the adduct formation mode is presented. NMR spectral characteristics of the free P=Se compounds 1–5 are described. Chirality 14:407–411, 2002. © 2002 Wiley‐Liss, Inc.