Synthesis and characterization of enantiopure copper(ii) complexes using chiral bidentate ligands

Kil Sik Min; A. Hyun Park; Jong Won Shin; Sankara Rao Rowthu; Seog K. Kim; Jae Jeong Ryoo

doi:10.1039/c0dt00380h

Synthesis and characterization of enantiopure copper(ii) complexes using chiral bidentate ligands

Kil Sik Min, A. Hyun Park, Jong Won Shin, Sankara Rao Rowthu, Seog K. Kim, Jae Jeong Ryoo

Department of Chemical Science Education

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

Chiral copper(ii) complexes of the types [Cu^II(R/S-ppme) ₃](ClO₄)₂ and [Cu^II(R/S-ppme) ₂(SO₄)] have been synthesized by reactions of Cu(ClO ₄)₂·6H₂O and CuSO₄· 5H₂O with R/S-ppme in methanol under aerobic conditions (R/S-ppme = (R/S)-(±)-1-phenyl-N-(pyridine-2-ylmethylene)ethanamine). All complexes were isolated and characterized by X-ray crystallography and circular dichroism (CD): (Λ)-[Cu^II(R-ppme)₃](ClO₄) ₂ (1), (Δ)-[Cu(S-ppme)₃](ClO₄) ₂·H₂O (2), (Δ)-[Cu^II(R-ppme) ₂(SO₄)]·4CH₃OH (3), and (Λ)-[Cu^II(S-ppme)₂(SO₄)]·4CH ₃OH (4). 1 and 2 with ClO₄^- anions are formed as tris(R/S-ppme) copper(ii) complexes, while 3 and 4 with SO₄ ^2- are formed as bis(R/S-ppme) copper(ii) complexes. The structures of 1 with R-ppmes and 4 with S-ppmes show the same absolute configurations (Λ). In contrast, 2 with S-ppmes and 3 with R-ppmes exhibit Δ configurations. In the electron paramagnetic resonance (EPR) spectra of 1 and 3, both compounds demonstrate z-axis elongated structures. The CD spectra of 1 and 2 show Cotton effects in an enantiomeric pattern; those of 3 and 4 also display the same effects.

Original language	English
Pages (from-to)	8741-8747
Number of pages	7
Journal	Dalton Transactions
Volume	39
Issue number	37
DOIs	https://doi.org/10.1039/c0dt00380h
State	Published - 7 Oct 2010

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@article{914c0c55188249e79e177638bbb54b64,

title = "Synthesis and characterization of enantiopure copper(ii) complexes using chiral bidentate ligands",

abstract = "Chiral copper(ii) complexes of the types [CuII(R/S-ppme) 3](ClO4)2 and [CuII(R/S-ppme) 2(SO4)] have been synthesized by reactions of Cu(ClO 4)2·6H2O and CuSO4· 5H2O with R/S-ppme in methanol under aerobic conditions (R/S-ppme = (R/S)-(±)-1-phenyl-N-(pyridine-2-ylmethylene)ethanamine). All complexes were isolated and characterized by X-ray crystallography and circular dichroism (CD): (Λ)-[CuII(R-ppme)3](ClO4) 2 (1), (Δ)-[Cu(S-ppme)3](ClO4) 2·H2O (2), (Δ)-[CuII(R-ppme) 2(SO4)]·4CH3OH (3), and (Λ)-[CuII(S-ppme)2(SO4)]·4CH 3OH (4). 1 and 2 with ClO4- anions are formed as tris(R/S-ppme) copper(ii) complexes, while 3 and 4 with SO4 2- are formed as bis(R/S-ppme) copper(ii) complexes. The structures of 1 with R-ppmes and 4 with S-ppmes show the same absolute configurations (Λ). In contrast, 2 with S-ppmes and 3 with R-ppmes exhibit Δ configurations. In the electron paramagnetic resonance (EPR) spectra of 1 and 3, both compounds demonstrate z-axis elongated structures. The CD spectra of 1 and 2 show Cotton effects in an enantiomeric pattern; those of 3 and 4 also display the same effects.",

author = "Min, {Kil Sik} and Park, {A. Hyun} and Shin, {Jong Won} and Rowthu, {Sankara Rao} and Kim, {Seog K.} and Ryoo, {Jae Jeong}",

year = "2010",

month = oct,

day = "7",

doi = "10.1039/c0dt00380h",

language = "English",

volume = "39",

pages = "8741--8747",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Synthesis and characterization of enantiopure copper(ii) complexes using chiral bidentate ligands

AU - Min, Kil Sik

AU - Park, A. Hyun

AU - Shin, Jong Won

AU - Rowthu, Sankara Rao

AU - Kim, Seog K.

AU - Ryoo, Jae Jeong

PY - 2010/10/7

Y1 - 2010/10/7

N2 - Chiral copper(ii) complexes of the types [CuII(R/S-ppme) 3](ClO4)2 and [CuII(R/S-ppme) 2(SO4)] have been synthesized by reactions of Cu(ClO 4)2·6H2O and CuSO4· 5H2O with R/S-ppme in methanol under aerobic conditions (R/S-ppme = (R/S)-(±)-1-phenyl-N-(pyridine-2-ylmethylene)ethanamine). All complexes were isolated and characterized by X-ray crystallography and circular dichroism (CD): (Λ)-[CuII(R-ppme)3](ClO4) 2 (1), (Δ)-[Cu(S-ppme)3](ClO4) 2·H2O (2), (Δ)-[CuII(R-ppme) 2(SO4)]·4CH3OH (3), and (Λ)-[CuII(S-ppme)2(SO4)]·4CH 3OH (4). 1 and 2 with ClO4- anions are formed as tris(R/S-ppme) copper(ii) complexes, while 3 and 4 with SO4 2- are formed as bis(R/S-ppme) copper(ii) complexes. The structures of 1 with R-ppmes and 4 with S-ppmes show the same absolute configurations (Λ). In contrast, 2 with S-ppmes and 3 with R-ppmes exhibit Δ configurations. In the electron paramagnetic resonance (EPR) spectra of 1 and 3, both compounds demonstrate z-axis elongated structures. The CD spectra of 1 and 2 show Cotton effects in an enantiomeric pattern; those of 3 and 4 also display the same effects.

AB - Chiral copper(ii) complexes of the types [CuII(R/S-ppme) 3](ClO4)2 and [CuII(R/S-ppme) 2(SO4)] have been synthesized by reactions of Cu(ClO 4)2·6H2O and CuSO4· 5H2O with R/S-ppme in methanol under aerobic conditions (R/S-ppme = (R/S)-(±)-1-phenyl-N-(pyridine-2-ylmethylene)ethanamine). All complexes were isolated and characterized by X-ray crystallography and circular dichroism (CD): (Λ)-[CuII(R-ppme)3](ClO4) 2 (1), (Δ)-[Cu(S-ppme)3](ClO4) 2·H2O (2), (Δ)-[CuII(R-ppme) 2(SO4)]·4CH3OH (3), and (Λ)-[CuII(S-ppme)2(SO4)]·4CH 3OH (4). 1 and 2 with ClO4- anions are formed as tris(R/S-ppme) copper(ii) complexes, while 3 and 4 with SO4 2- are formed as bis(R/S-ppme) copper(ii) complexes. The structures of 1 with R-ppmes and 4 with S-ppmes show the same absolute configurations (Λ). In contrast, 2 with S-ppmes and 3 with R-ppmes exhibit Δ configurations. In the electron paramagnetic resonance (EPR) spectra of 1 and 3, both compounds demonstrate z-axis elongated structures. The CD spectra of 1 and 2 show Cotton effects in an enantiomeric pattern; those of 3 and 4 also display the same effects.

UR - http://www.scopus.com/inward/record.url?scp=77956492512&partnerID=8YFLogxK

U2 - 10.1039/c0dt00380h

DO - 10.1039/c0dt00380h

M3 - Article

C2 - 20694221

AN - SCOPUS:77956492512

SN - 1477-9226

VL - 39

SP - 8741

EP - 8747

JO - Dalton Transactions

JF - Dalton Transactions

IS - 37

ER -

Synthesis and characterization of enantiopure copper(ii) complexes using chiral bidentate ligands

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