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Synthesis and structures of chiral halo[ N, N-dimethyl- α-(2-naphthyl)ethylamine-3,C,N] mercury (II) complexes
HgCl 2 reacts with enantiomerically pure 3-lithio-( S)-(−) or ( R)-(+)- N, N-dimethyl- α-(2-naphthyl)ethylamine, ( S) or ( R)-LiTMNA, to produce ( S) c( R) Hg-{HgCl[C 10H 6CH(Me)NMe 2]}, 2a′, or ( S) c( R) Hg-{HgCl[C 10H 6CH(Me)NMe 2]}, 2a, in fair yields. The bromide ( 2b) and iodide ( 2c) analogs...
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Published in: | Journal of molecular structure 1999-02, Vol.475 (2), p.121-130 |
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Main Authors: | , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | HgCl
2 reacts with enantiomerically pure 3-lithio-(
S)-(−) or (
R)-(+)-
N,
N-dimethyl-
α-(2-naphthyl)ethylamine, (
S) or (
R)-LiTMNA, to produce (
S)
c(
R)
Hg-{HgCl[C
10H
6CH(Me)NMe
2]},
2a′, or (
S)
c(
R)
Hg-{HgCl[C
10H
6CH(Me)NMe
2]},
2a, in fair yields. The bromide (
2b) and iodide (
2c) analogs were prepared in good yields by reaction of
2a with NaBr and NaI, respectively. The crystal structures of
2a′,
2b and
2c show that the Hg atom in each compound is three-coordinate, T-shaped, and slightly pyramidal in the solid state. These three compounds form exclusively as the (
S)
c(
R)
Hg or (
R)
c(
S)
Hg diastereomers with average Hg–C and Hg–N distances of 2.08 (2) Å and 2.65 (2) Å, respectively. The Hg–N bond is weak and is easily cleaved in solution to form temperature-dependent equilibrium mixtures of two- and three-coordinate species as deduced from variable temperature NMR spectroscopy. |
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ISSN: | 0022-2860 1872-8014 |
DOI: | 10.1016/S0022-2860(98)00509-2 |