Two new Ni(II) Schiff base complexes: X-ray absolute structure determination, synthesis of a N-15-labelled complex and full assignment of its H-1 NMR and C-13 NMR spectra

Vratislav Langer; Alexander Popkov; Milan Nadvornik; Antonin Lycka

doi:10.1016/j.poly.2006.09.103

Two new Ni(II) Schiff base complexes: X-ray absolute structure determination, synthesis of a N-15-labelled complex and full assignment of its H-1 NMR and C-13 NMR spectra

Vratislav Langer^*, Alexander Popkov, Milan Nadvornik, Antonin Lycka

^*Corresponding author for this work

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

8 Citations (Scopus)

Abstract

The Ni(II) complex of the Schiff base of (S)-N-(2-benzoyl-4-chlorophenyl)-1-benzylpyrrolidine-2-carboxamide and glycine (1) [GKCI] and the hemihydrate of the Ni(II) complex of the Schiff base of (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide and 2-aminoisobutiric acid (2) Me(2)GK] were prepared and their absolute structures determined. The conformations of the complexes and their hydrogen bonding are discussed in detail. In complex 2, the repulsion between the benzyl group and an equatorial methyl group should affect the conformation of the benzyl group, distribution of the pi-electron density in this group and distortion of the internal coordination sphere, while for complex 1, only minor conformational changes were expected. H-1 and C-13 NMR data for the N-15-labelled complex 2 were acquired and fully assigned in order to study the influence of pi-electron density of the benzyl group to the long-range C-13-N-15 and C-13-C-13 spin-spin interactions. (c) 2006 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	911-917
Number of pages	7
Journal	Polyhedron
Volume	26
Issue number	4
DOIs	https://doi.org/10.1016/j.poly.2006.09.103
Publication status	Published - 1-Mar-2007

Keywords

complexes
crystal structure
NMR spectra
spin-spin interactions
ALPHA-AMINO-ACIDS
PHASE-TRANSFER CATALYSIS
EFFICIENT ASYMMETRIC-SYNTHESIS
SUBSTITUTED GLUTAMIC ACIDS
MICHAEL ADDITION-REACTIONS
REUSABLE CHIRAL AUXILIARY
ENANTIOSELECTIVE SYNTHESIS
NUCLEOPHILIC GLYCINE
DIASTEREOSELECTIVE SYNTHESIS
NICKEL(II) COMPLEXES

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CCDC 294430: Experimental Crystal Structure Determination
Langer, V. (Contributor), Popkov, A. (Contributor), Nádvorník, M. (Contributor) & Lyčka, A. (Contributor), University of Groningen, 4-Jan-2006
DOI: 10.5517/cc9wcr8
Dataset
CCDC 294429: Experimental Crystal Structure Determination
Langer, V. (Contributor), Popkov, A. (Contributor), Nádvorník, M. (Contributor) & Lyčka, A. (Contributor), University of Groningen, 4-Jan-2006
DOI: 10.5517/cc9wcq7
Dataset

Cite this

@article{4f3f7f960f6f400a90c958bc292405c5,

title = "Two new Ni(II) Schiff base complexes: X-ray absolute structure determination, synthesis of a N-15-labelled complex and full assignment of its H-1 NMR and C-13 NMR spectra",

abstract = "The Ni(II) complex of the Schiff base of (S)-N-(2-benzoyl-4-chlorophenyl)-1-benzylpyrrolidine-2-carboxamide and glycine (1) [GKCI] and the hemihydrate of the Ni(II) complex of the Schiff base of (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide and 2-aminoisobutiric acid (2) Me(2)GK] were prepared and their absolute structures determined. The conformations of the complexes and their hydrogen bonding are discussed in detail. In complex 2, the repulsion between the benzyl group and an equatorial methyl group should affect the conformation of the benzyl group, distribution of the pi-electron density in this group and distortion of the internal coordination sphere, while for complex 1, only minor conformational changes were expected. H-1 and C-13 NMR data for the N-15-labelled complex 2 were acquired and fully assigned in order to study the influence of pi-electron density of the benzyl group to the long-range C-13-N-15 and C-13-C-13 spin-spin interactions. (c) 2006 Elsevier Ltd. All rights reserved.",

keywords = "complexes, crystal structure, NMR spectra, spin-spin interactions, ALPHA-AMINO-ACIDS, PHASE-TRANSFER CATALYSIS, EFFICIENT ASYMMETRIC-SYNTHESIS, SUBSTITUTED GLUTAMIC ACIDS, MICHAEL ADDITION-REACTIONS, REUSABLE CHIRAL AUXILIARY, ENANTIOSELECTIVE SYNTHESIS, NUCLEOPHILIC GLYCINE, DIASTEREOSELECTIVE SYNTHESIS, NICKEL(II) COMPLEXES",

author = "Vratislav Langer and Alexander Popkov and Milan Nadvornik and Antonin Lycka",

year = "2007",

month = mar,

day = "1",

doi = "10.1016/j.poly.2006.09.103",

language = "English",

volume = "26",

pages = "911--917",

journal = "Polyhedron",

issn = "0277-5387",

publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

number = "4",

}

Two new Ni(II) Schiff base complexes: X-ray absolute structure determination, synthesis of a N-15-labelled complex and full assignment of its H-1 NMR and C-13 NMR spectra. / Langer, Vratislav; Popkov, Alexander; Nadvornik, Milan et al.
In: Polyhedron, Vol. 26, No. 4, 01.03.2007, p. 911-917.

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

TY - JOUR

T1 - Two new Ni(II) Schiff base complexes

T2 - X-ray absolute structure determination, synthesis of a N-15-labelled complex and full assignment of its H-1 NMR and C-13 NMR spectra

AU - Langer, Vratislav

AU - Popkov, Alexander

AU - Nadvornik, Milan

AU - Lycka, Antonin

PY - 2007/3/1

Y1 - 2007/3/1

N2 - The Ni(II) complex of the Schiff base of (S)-N-(2-benzoyl-4-chlorophenyl)-1-benzylpyrrolidine-2-carboxamide and glycine (1) [GKCI] and the hemihydrate of the Ni(II) complex of the Schiff base of (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide and 2-aminoisobutiric acid (2) Me(2)GK] were prepared and their absolute structures determined. The conformations of the complexes and their hydrogen bonding are discussed in detail. In complex 2, the repulsion between the benzyl group and an equatorial methyl group should affect the conformation of the benzyl group, distribution of the pi-electron density in this group and distortion of the internal coordination sphere, while for complex 1, only minor conformational changes were expected. H-1 and C-13 NMR data for the N-15-labelled complex 2 were acquired and fully assigned in order to study the influence of pi-electron density of the benzyl group to the long-range C-13-N-15 and C-13-C-13 spin-spin interactions. (c) 2006 Elsevier Ltd. All rights reserved.

AB - The Ni(II) complex of the Schiff base of (S)-N-(2-benzoyl-4-chlorophenyl)-1-benzylpyrrolidine-2-carboxamide and glycine (1) [GKCI] and the hemihydrate of the Ni(II) complex of the Schiff base of (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide and 2-aminoisobutiric acid (2) Me(2)GK] were prepared and their absolute structures determined. The conformations of the complexes and their hydrogen bonding are discussed in detail. In complex 2, the repulsion between the benzyl group and an equatorial methyl group should affect the conformation of the benzyl group, distribution of the pi-electron density in this group and distortion of the internal coordination sphere, while for complex 1, only minor conformational changes were expected. H-1 and C-13 NMR data for the N-15-labelled complex 2 were acquired and fully assigned in order to study the influence of pi-electron density of the benzyl group to the long-range C-13-N-15 and C-13-C-13 spin-spin interactions. (c) 2006 Elsevier Ltd. All rights reserved.

KW - complexes

KW - crystal structure

KW - NMR spectra

KW - spin-spin interactions

KW - ALPHA-AMINO-ACIDS

KW - PHASE-TRANSFER CATALYSIS

KW - EFFICIENT ASYMMETRIC-SYNTHESIS

KW - SUBSTITUTED GLUTAMIC ACIDS

KW - MICHAEL ADDITION-REACTIONS

KW - REUSABLE CHIRAL AUXILIARY

KW - ENANTIOSELECTIVE SYNTHESIS

KW - NUCLEOPHILIC GLYCINE

KW - DIASTEREOSELECTIVE SYNTHESIS

KW - NICKEL(II) COMPLEXES

U2 - 10.1016/j.poly.2006.09.103

DO - 10.1016/j.poly.2006.09.103

M3 - Article

SN - 0277-5387

VL - 26

SP - 911

EP - 917

JO - Polyhedron

JF - Polyhedron

IS - 4

ER -

Two new Ni(II) Schiff base complexes: X-ray absolute structure determination, synthesis of a N-15-labelled complex and full assignment of its H-1 NMR and C-13 NMR spectra

Abstract

Keywords

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Datasets

CCDC 294430: Experimental Crystal Structure Determination

CCDC 294429: Experimental Crystal Structure Determination

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