Predictions and methods of separation of racemic bidentate ligands via stereoselective ligand exchange reactions

Paul V. Bernhardt, Peter Comba, Thomas Gyr, K. Várnagy

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Abstract

The technique of molecular mechanics has been applied to the prediction of isomer distributions of several complexes of chiral quadridentate amine ligands in conjunction with some optically active bidentate substrates. Specifically, the systems reported comprise the cobalt(III) and nickel(II) complexes of N,N′-bis[2(S)-2-pyrrolidinylmethyl]ethane-1,2-diamine (S,S-epm) and N,N′-bis[2(S)-2-pyrrolidinylmethyl]propane-1,3-diamine (S,S-ppm) in combination with the chiral bidentate ligands propane-1,2-diamine, (pn) 2-pyrrolidinylmethanamine (pam), and alanine (ala). Agreement between all predicted and observed isomer ratios was within 5%. The experimentally determined enantiomer ratios were as follows: [Co(S,S-ppm)(pn)]3+, 49/51 R-pn/S-pn; [Ni(S,S-ppm)(pn)]2+, 57/43 R-pn/S-pn; [Ni(S,S-ppm)(pam)]2+, 44/56 R-pam/S-pam; [Ni(S,S-epm)(pn)]2+, 43/57 R-pn/S-pn; [Ni(S,S-epm)(pam)]2+, 70/30 R-pam/S-pam. Various experimental methods are reported for the determination of chiral separation.

Original languageEnglish
Pages (from-to)1220-1223
Number of pages4
JournalInorganic Chemistry
Volume31
Issue number7
Publication statusPublished - 1992

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Propane
ethylenediamine
Diamines
diamines
Isomers
Ion exchange
Ligands
propane
ligands
Molecular mechanics
Enantiomers
isomers
Cobalt
predictions
Nickel
Alanine
Amines
enantiomers
alanine
ethane

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Predictions and methods of separation of racemic bidentate ligands via stereoselective ligand exchange reactions. / Bernhardt, Paul V.; Comba, Peter; Gyr, Thomas; Várnagy, K.

In: Inorganic Chemistry, Vol. 31, No. 7, 1992, p. 1220-1223.

Research output: Contribution to journalArticle

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abstract = "The technique of molecular mechanics has been applied to the prediction of isomer distributions of several complexes of chiral quadridentate amine ligands in conjunction with some optically active bidentate substrates. Specifically, the systems reported comprise the cobalt(III) and nickel(II) complexes of N,N′-bis[2(S)-2-pyrrolidinylmethyl]ethane-1,2-diamine (S,S-epm) and N,N′-bis[2(S)-2-pyrrolidinylmethyl]propane-1,3-diamine (S,S-ppm) in combination with the chiral bidentate ligands propane-1,2-diamine, (pn) 2-pyrrolidinylmethanamine (pam), and alanine (ala). Agreement between all predicted and observed isomer ratios was within 5{\%}. The experimentally determined enantiomer ratios were as follows: [Co(S,S-ppm)(pn)]3+, 49/51 R-pn/S-pn; [Ni(S,S-ppm)(pn)]2+, 57/43 R-pn/S-pn; [Ni(S,S-ppm)(pam)]2+, 44/56 R-pam/S-pam; [Ni(S,S-epm)(pn)]2+, 43/57 R-pn/S-pn; [Ni(S,S-epm)(pam)]2+, 70/30 R-pam/S-pam. Various experimental methods are reported for the determination of chiral separation.",
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N2 - The technique of molecular mechanics has been applied to the prediction of isomer distributions of several complexes of chiral quadridentate amine ligands in conjunction with some optically active bidentate substrates. Specifically, the systems reported comprise the cobalt(III) and nickel(II) complexes of N,N′-bis[2(S)-2-pyrrolidinylmethyl]ethane-1,2-diamine (S,S-epm) and N,N′-bis[2(S)-2-pyrrolidinylmethyl]propane-1,3-diamine (S,S-ppm) in combination with the chiral bidentate ligands propane-1,2-diamine, (pn) 2-pyrrolidinylmethanamine (pam), and alanine (ala). Agreement between all predicted and observed isomer ratios was within 5%. The experimentally determined enantiomer ratios were as follows: [Co(S,S-ppm)(pn)]3+, 49/51 R-pn/S-pn; [Ni(S,S-ppm)(pn)]2+, 57/43 R-pn/S-pn; [Ni(S,S-ppm)(pam)]2+, 44/56 R-pam/S-pam; [Ni(S,S-epm)(pn)]2+, 43/57 R-pn/S-pn; [Ni(S,S-epm)(pam)]2+, 70/30 R-pam/S-pam. Various experimental methods are reported for the determination of chiral separation.

AB - The technique of molecular mechanics has been applied to the prediction of isomer distributions of several complexes of chiral quadridentate amine ligands in conjunction with some optically active bidentate substrates. Specifically, the systems reported comprise the cobalt(III) and nickel(II) complexes of N,N′-bis[2(S)-2-pyrrolidinylmethyl]ethane-1,2-diamine (S,S-epm) and N,N′-bis[2(S)-2-pyrrolidinylmethyl]propane-1,3-diamine (S,S-ppm) in combination with the chiral bidentate ligands propane-1,2-diamine, (pn) 2-pyrrolidinylmethanamine (pam), and alanine (ala). Agreement between all predicted and observed isomer ratios was within 5%. The experimentally determined enantiomer ratios were as follows: [Co(S,S-ppm)(pn)]3+, 49/51 R-pn/S-pn; [Ni(S,S-ppm)(pn)]2+, 57/43 R-pn/S-pn; [Ni(S,S-ppm)(pam)]2+, 44/56 R-pam/S-pam; [Ni(S,S-epm)(pn)]2+, 43/57 R-pn/S-pn; [Ni(S,S-epm)(pam)]2+, 70/30 R-pam/S-pam. Various experimental methods are reported for the determination of chiral separation.

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