Copper(II) coordination polymers of arylhydrazone of 1H-indene-1,3(2H)-dione linked by 4,4′-bipyridineor hexamethylenetetramine

Evaluation of catalytic activity in Henry reaction

Gonçalo A.O. Tiago, Kamran T. Mahmudov, M. Fátima C. Guedes da Silva, Ana P.C. Ribeiro, Fatali E. Huseynov, Luís C. Branco, Armando J.L. Pombeiro

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The 1D and the 2D copper(II) coordination polymers [{Cu(κN,OO′-L)}2(μ-1κN:2κN′-bpy)2]n (1) and [{Cu(μ-1κN,OO′:2κO″-L)}2(μ-1κN:2κN′-hmt)]n (2), respectively, were synthesized from copper(II) nitrate and sodium 2-(2-(1,3-dioxo-1H-inden-2(3H)-ylidene) hydrazinyl)benzenesulfonate (NaHL), in the presence of 4,4′-bipyridine (4,4′-bpy) (for 1) or hexamethylenetetramine (hmt) (for 2). 1 and 2 are water soluble and are characterized by elemental analysis, IR spectroscopy, ESI-MS and single crystal X-ray diffraction. Depending on the neutral linkers, the dianionic ligand L2− displays tri- (in 1) or tetradentate (in 2) binding modes. The Cu2+ in 1 adopts a distorted N3O2 square-pyramid coordination environment, while in 2 it displays a distorted N2O3 trigonal bipyramid geometry. The catalytic activity of 1 and 2 was evaluated in the diastereoselective Henry reaction of nitroethane with a variety of aromatic and aliphatic aldehydes, in water and in organic solvents. β-Hydroxy nitroalkanes were obtained in high yields (up to 92%), and moderate-to-good syn/anti diastereoselectivities (up to 79:21), in water at room temperature.

Original languageEnglish
Pages (from-to)33-39
Number of pages7
JournalPolyhedron
Volume133
DOIs
Publication statusPublished - 5 Sep 2017

Fingerprint

Methenamine
indene
hexamethylenetetramine
Dione
coordination polymers
catalytic activity
Copper
Catalyst activity
Polymers
copper
Water
evaluation
water
pyramids
Aldehydes
aldehydes
Organic solvents
nitrates
Infrared spectroscopy
Nitrates

Keywords

  • 4,4′-Bipyridine
  • Arylhydrazone of 1H-indene-1,3(2H)-dione
  • Copper(II) complexes
  • Henry reaction in water
  • Hexamethylenetetramine

Cite this

Tiago, Gonçalo A.O. ; Mahmudov, Kamran T. ; Guedes da Silva, M. Fátima C. ; Ribeiro, Ana P.C. ; Huseynov, Fatali E. ; Branco, Luís C. ; Pombeiro, Armando J.L. / Copper(II) coordination polymers of arylhydrazone of 1H-indene-1,3(2H)-dione linked by 4,4′-bipyridineor hexamethylenetetramine : Evaluation of catalytic activity in Henry reaction. In: Polyhedron. 2017 ; Vol. 133. pp. 33-39.
@article{04a5f0dc98cc43d498e1a94258d16eaf,
title = "Copper(II) coordination polymers of arylhydrazone of 1H-indene-1,3(2H)-dione linked by 4,4′-bipyridineor hexamethylenetetramine: Evaluation of catalytic activity in Henry reaction",
abstract = "The 1D and the 2D copper(II) coordination polymers [{Cu(κN,OO′-L)}2(μ-1κN:2κN′-bpy)2]n (1) and [{Cu(μ-1κN,OO′:2κO″-L)}2(μ-1κN:2κN′-hmt)]n (2), respectively, were synthesized from copper(II) nitrate and sodium 2-(2-(1,3-dioxo-1H-inden-2(3H)-ylidene) hydrazinyl)benzenesulfonate (NaHL), in the presence of 4,4′-bipyridine (4,4′-bpy) (for 1) or hexamethylenetetramine (hmt) (for 2). 1 and 2 are water soluble and are characterized by elemental analysis, IR spectroscopy, ESI-MS and single crystal X-ray diffraction. Depending on the neutral linkers, the dianionic ligand L2− displays tri- (in 1) or tetradentate (in 2) binding modes. The Cu2+ in 1 adopts a distorted N3O2 square-pyramid coordination environment, while in 2 it displays a distorted N2O3 trigonal bipyramid geometry. The catalytic activity of 1 and 2 was evaluated in the diastereoselective Henry reaction of nitroethane with a variety of aromatic and aliphatic aldehydes, in water and in organic solvents. β-Hydroxy nitroalkanes were obtained in high yields (up to 92{\%}), and moderate-to-good syn/anti diastereoselectivities (up to 79:21), in water at room temperature.",
keywords = "4,4′-Bipyridine, Arylhydrazone of 1H-indene-1,3(2H)-dione, Copper(II) complexes, Henry reaction in water, Hexamethylenetetramine",
author = "Tiago, {Gon{\cc}alo A.O.} and Mahmudov, {Kamran T.} and {Guedes da Silva}, {M. F{\'a}tima C.} and Ribeiro, {Ana P.C.} and Huseynov, {Fatali E.} and Branco, {Lu{\'i}s C.} and Pombeiro, {Armando J.L.}",
note = "sem pdf conforme despacho. Foundation for Science and Technology (FCT), Portugal - UID/QUI/00100/2013 ; Ministry of Education and Science of the Russian Federation - 02.a03.21.0008 ; CATSUS of FCT - PD/BD/106015/2014 ; SFRH/BPD/90883/2012.",
year = "2017",
month = "9",
day = "5",
doi = "10.1016/j.poly.2017.05.013",
language = "English",
volume = "133",
pages = "33--39",
journal = "Polyhedron",
issn = "0277-5387",
publisher = "Elsevier Ltd",

}

Copper(II) coordination polymers of arylhydrazone of 1H-indene-1,3(2H)-dione linked by 4,4′-bipyridineor hexamethylenetetramine : Evaluation of catalytic activity in Henry reaction. / Tiago, Gonçalo A.O.; Mahmudov, Kamran T.; Guedes da Silva, M. Fátima C.; Ribeiro, Ana P.C.; Huseynov, Fatali E.; Branco, Luís C.; Pombeiro, Armando J.L.

In: Polyhedron, Vol. 133, 05.09.2017, p. 33-39.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Copper(II) coordination polymers of arylhydrazone of 1H-indene-1,3(2H)-dione linked by 4,4′-bipyridineor hexamethylenetetramine

T2 - Evaluation of catalytic activity in Henry reaction

AU - Tiago, Gonçalo A.O.

AU - Mahmudov, Kamran T.

AU - Guedes da Silva, M. Fátima C.

AU - Ribeiro, Ana P.C.

AU - Huseynov, Fatali E.

AU - Branco, Luís C.

AU - Pombeiro, Armando J.L.

N1 - sem pdf conforme despacho. Foundation for Science and Technology (FCT), Portugal - UID/QUI/00100/2013 ; Ministry of Education and Science of the Russian Federation - 02.a03.21.0008 ; CATSUS of FCT - PD/BD/106015/2014 ; SFRH/BPD/90883/2012.

PY - 2017/9/5

Y1 - 2017/9/5

N2 - The 1D and the 2D copper(II) coordination polymers [{Cu(κN,OO′-L)}2(μ-1κN:2κN′-bpy)2]n (1) and [{Cu(μ-1κN,OO′:2κO″-L)}2(μ-1κN:2κN′-hmt)]n (2), respectively, were synthesized from copper(II) nitrate and sodium 2-(2-(1,3-dioxo-1H-inden-2(3H)-ylidene) hydrazinyl)benzenesulfonate (NaHL), in the presence of 4,4′-bipyridine (4,4′-bpy) (for 1) or hexamethylenetetramine (hmt) (for 2). 1 and 2 are water soluble and are characterized by elemental analysis, IR spectroscopy, ESI-MS and single crystal X-ray diffraction. Depending on the neutral linkers, the dianionic ligand L2− displays tri- (in 1) or tetradentate (in 2) binding modes. The Cu2+ in 1 adopts a distorted N3O2 square-pyramid coordination environment, while in 2 it displays a distorted N2O3 trigonal bipyramid geometry. The catalytic activity of 1 and 2 was evaluated in the diastereoselective Henry reaction of nitroethane with a variety of aromatic and aliphatic aldehydes, in water and in organic solvents. β-Hydroxy nitroalkanes were obtained in high yields (up to 92%), and moderate-to-good syn/anti diastereoselectivities (up to 79:21), in water at room temperature.

AB - The 1D and the 2D copper(II) coordination polymers [{Cu(κN,OO′-L)}2(μ-1κN:2κN′-bpy)2]n (1) and [{Cu(μ-1κN,OO′:2κO″-L)}2(μ-1κN:2κN′-hmt)]n (2), respectively, were synthesized from copper(II) nitrate and sodium 2-(2-(1,3-dioxo-1H-inden-2(3H)-ylidene) hydrazinyl)benzenesulfonate (NaHL), in the presence of 4,4′-bipyridine (4,4′-bpy) (for 1) or hexamethylenetetramine (hmt) (for 2). 1 and 2 are water soluble and are characterized by elemental analysis, IR spectroscopy, ESI-MS and single crystal X-ray diffraction. Depending on the neutral linkers, the dianionic ligand L2− displays tri- (in 1) or tetradentate (in 2) binding modes. The Cu2+ in 1 adopts a distorted N3O2 square-pyramid coordination environment, while in 2 it displays a distorted N2O3 trigonal bipyramid geometry. The catalytic activity of 1 and 2 was evaluated in the diastereoselective Henry reaction of nitroethane with a variety of aromatic and aliphatic aldehydes, in water and in organic solvents. β-Hydroxy nitroalkanes were obtained in high yields (up to 92%), and moderate-to-good syn/anti diastereoselectivities (up to 79:21), in water at room temperature.

KW - 4,4′-Bipyridine

KW - Arylhydrazone of 1H-indene-1,3(2H)-dione

KW - Copper(II) complexes

KW - Henry reaction in water

KW - Hexamethylenetetramine

UR - http://www.scopus.com/inward/record.url?scp=85019833528&partnerID=8YFLogxK

U2 - 10.1016/j.poly.2017.05.013

DO - 10.1016/j.poly.2017.05.013

M3 - Article

VL - 133

SP - 33

EP - 39

JO - Polyhedron

JF - Polyhedron

SN - 0277-5387

ER -