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

Gyeongnam Science High School
Kyungpook National University
Yeungnam University

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",

number = "37",

}

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 - https://www.scopus.com/pages/publications/77956492512

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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