Synthesis and characterization of nickel(II) complex containing 2-(t-butylaminomethyl)pyrrole

Hsieh Chang-Chih, Chao Wan-Jung, Horng Yih-Chern, Hon Man Lee

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Two aminopyrroles, 2-(t-butylaminomethyl)pyrrole (HL1) and 2,5-di(t-butylaminomethyl)pyrrole (HL2), were synthesized and the hydrogen-bond interactions were observed in the single-crystal X-ray structures of HL1-HCl and HL2. Bis[2-(t-butylaminomethyl)pyrrole]nickel(II) [Ni(L1)2] was prepared by treatment of the NiCl2 with 2 equiv. of mono-deprotonated HL1 in THF solvent. The solid-state structure of Ni(L1)2 shows the N4-coordinated nickel atom, with a geometry corresponding to a square-planar structure, in which two intramolecular C-H⋯Ni interactions are present at the axial positions with contact distances of 2.77 Å. The complex displays an irreversible reduction response at -0.66 V (vs. Fc +/Fc) in CH3CN. Furthermore, 1H, 13C-HSQC NMR experiments performed at room temperature revealed that the two methylene protons of the chelating L1-1 are chemically nonequivalent and one of them is coupled to the amino proton. The coupling constants (JHH') observed are close to the values predicted from the vicinal Karplus correlation diagram.

Original languageEnglish
Pages (from-to)435-442
Number of pages8
JournalJournal of the Chinese Chemical Society
Volume56
Issue number2
Publication statusPublished - 2009 Sep 7

Fingerprint

Pyrroles
Nickel
Protons
Chelation
Hydrogen bonds
Nuclear magnetic resonance
Single crystals
X rays
Atoms
Geometry
Experiments
Temperature

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

@article{6382caa03dd94a2c81e78f9df084e073,
title = "Synthesis and characterization of nickel(II) complex containing 2-(t-butylaminomethyl)pyrrole",
abstract = "Two aminopyrroles, 2-(t-butylaminomethyl)pyrrole (HL1) and 2,5-di(t-butylaminomethyl)pyrrole (HL2), were synthesized and the hydrogen-bond interactions were observed in the single-crystal X-ray structures of HL1-HCl and HL2. Bis[2-(t-butylaminomethyl)pyrrole]nickel(II) [Ni(L1)2] was prepared by treatment of the NiCl2 with 2 equiv. of mono-deprotonated HL1 in THF solvent. The solid-state structure of Ni(L1)2 shows the N4-coordinated nickel atom, with a geometry corresponding to a square-planar structure, in which two intramolecular C-H⋯Ni interactions are present at the axial positions with contact distances of 2.77 {\AA}. The complex displays an irreversible reduction response at -0.66 V (vs. Fc +/Fc) in CH3CN. Furthermore, 1H, 13C-HSQC NMR experiments performed at room temperature revealed that the two methylene protons of the chelating L1-1 are chemically nonequivalent and one of them is coupled to the amino proton. The coupling constants (JHH') observed are close to the values predicted from the vicinal Karplus correlation diagram.",
author = "Hsieh Chang-Chih and Chao Wan-Jung and Horng Yih-Chern and Lee, {Hon Man}",
year = "2009",
month = "9",
day = "7",
language = "English",
volume = "56",
pages = "435--442",
journal = "Journal of the Chinese Chemical Society",
issn = "0009-4536",
publisher = "Chinese Chemical Society",
number = "2",

}

Synthesis and characterization of nickel(II) complex containing 2-(t-butylaminomethyl)pyrrole. / Chang-Chih, Hsieh; Wan-Jung, Chao; Yih-Chern, Horng; Lee, Hon Man.

In: Journal of the Chinese Chemical Society, Vol. 56, No. 2, 07.09.2009, p. 435-442.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and characterization of nickel(II) complex containing 2-(t-butylaminomethyl)pyrrole

AU - Chang-Chih, Hsieh

AU - Wan-Jung, Chao

AU - Yih-Chern, Horng

AU - Lee, Hon Man

PY - 2009/9/7

Y1 - 2009/9/7

N2 - Two aminopyrroles, 2-(t-butylaminomethyl)pyrrole (HL1) and 2,5-di(t-butylaminomethyl)pyrrole (HL2), were synthesized and the hydrogen-bond interactions were observed in the single-crystal X-ray structures of HL1-HCl and HL2. Bis[2-(t-butylaminomethyl)pyrrole]nickel(II) [Ni(L1)2] was prepared by treatment of the NiCl2 with 2 equiv. of mono-deprotonated HL1 in THF solvent. The solid-state structure of Ni(L1)2 shows the N4-coordinated nickel atom, with a geometry corresponding to a square-planar structure, in which two intramolecular C-H⋯Ni interactions are present at the axial positions with contact distances of 2.77 Å. The complex displays an irreversible reduction response at -0.66 V (vs. Fc +/Fc) in CH3CN. Furthermore, 1H, 13C-HSQC NMR experiments performed at room temperature revealed that the two methylene protons of the chelating L1-1 are chemically nonequivalent and one of them is coupled to the amino proton. The coupling constants (JHH') observed are close to the values predicted from the vicinal Karplus correlation diagram.

AB - Two aminopyrroles, 2-(t-butylaminomethyl)pyrrole (HL1) and 2,5-di(t-butylaminomethyl)pyrrole (HL2), were synthesized and the hydrogen-bond interactions were observed in the single-crystal X-ray structures of HL1-HCl and HL2. Bis[2-(t-butylaminomethyl)pyrrole]nickel(II) [Ni(L1)2] was prepared by treatment of the NiCl2 with 2 equiv. of mono-deprotonated HL1 in THF solvent. The solid-state structure of Ni(L1)2 shows the N4-coordinated nickel atom, with a geometry corresponding to a square-planar structure, in which two intramolecular C-H⋯Ni interactions are present at the axial positions with contact distances of 2.77 Å. The complex displays an irreversible reduction response at -0.66 V (vs. Fc +/Fc) in CH3CN. Furthermore, 1H, 13C-HSQC NMR experiments performed at room temperature revealed that the two methylene protons of the chelating L1-1 are chemically nonequivalent and one of them is coupled to the amino proton. The coupling constants (JHH') observed are close to the values predicted from the vicinal Karplus correlation diagram.

UR - http://www.scopus.com/inward/record.url?scp=69549124088&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=69549124088&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:69549124088

VL - 56

SP - 435

EP - 442

JO - Journal of the Chinese Chemical Society

JF - Journal of the Chinese Chemical Society

SN - 0009-4536

IS - 2

ER -