Details

Autor(en) / Beteiligte

• Gheorghe, Ruxandra
• Chamoreau, Lise-Marie
• Kapitan, Josef
• Ovanesyan, Nikolaï S.
• Aldoshin, Sergei M.
• Hecht, Lutz
• Barron, Laurence D.
• Train, Cyrille
• Gruselle, Michel

Titel

Enantiomerically pure quaternary ammonium salts with a chiral alkyl chain N(CH3)(n-C3H7)2(sec-C4H9)I: Synthesis and physical studies

Ist Teil von

• Chirality (New York, N.Y.), 2008-11, Vol.20 (10), p.1085-1091

Ort / Verlag

Hoboken: Wiley Subscription Services, Inc., A Wiley Company

Erscheinungsjahr

2008

Quelle

Wiley Online Library

Beschreibungen/Notizen

• A pair of enantiomerically pure quaternary ammonium salts with a chiral side chain, methyl‐(R)‐(1‐methylpropyl)di(n‐propyl)ammonium iodide 1 and methyl‐(S)‐(1‐methylpropyl)di(n‐propyl)ammonium iodide 2, and the related racemate, methyl‐(rac)‐(1‐methylpropyl)di(n‐propyl)ammonium iodide 3, were synthesized through a reductive alkylation procedure, starting from enantiomerically pure and, also, racemic forms of (rac)‐(1‐methylpropyl)amine. A spectroscopic chiroptical signature in solution was provided by the Raman optical activity spectra of compounds 1 and 2. The crystallographic structures of 1, 2, and 3 were examined by single crystal X‐ray diffraction. 1 crystallizes in the tetragonal space group P43212 (no. 96), a = b = 12.826 (2) Å, c = 17.730 (2) Å, V = 2916.9 (5) Å3, Z = 8, Flack coefficient 0.04 (2). 2 crystallizes in the tetragonal space group P41212 (no. 92), a = b = 12.842 (1) Å, c = 17.749 (2) Å, V = 2927.0 (5) Å3, Z = 8, Flack coefficient 0.05 (2). The crystal structures and space groups for 1 and 2 are enantiomorphs and the crystallographic investigation confirmed the absolute configuration of the stereocenter in both compounds. 3 crystallizes in the monoclinic space group P21/n(no. 14), a = 8.178 (1) Å, b = 14.309 (2) Å, c = 12.328 (2) Å, β = 96.811 (6)o, V = 1432.4 (2) Å3, Z = 4. Chirality, 2008. © 2008 Wiley‐Liss, Inc.