Novel nickel(II) complex bearing phthalimido ligands derived from oxime-mediated transformation of phthalonitrile

Kopylovich, Maximilian N.; Haukka, Matti; Kirillov, Alexander M.; Kukushkin, Vadim Yu.; Pombeiro, Armando J. L.

doi:10.1016/j.inoche.2007.10.018

Cited by 10 publications

(7 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Reflux of 2 equiv of Me 2 CNOH with phthalodinitrile and Ni(NO 3 ) 2 •6H 2 O in acetone led to in situ formation of 88 (Scheme 41, a). 253 This reaction consists of two consecutive addition steps. The addition of 2 equiv of ethylenediamine to the reaction mixture furnishes 89 (77%; b).…”

Section: Chemical Reviewsmentioning

confidence: 99%

Metal-Involving Synthesis and Reactions of Oximes

et al. 2017

Self Cite

View full text Add to dashboard Cite

This review classifies and summarizes the past 10-15 years of advancements in the field of metal-involving (i.e., metal-mediated and metal-catalyzed) reactions of oximes. These reactions are diverse in nature and have been employed for syntheses of oxime-based metal complexes and cage-compounds, oxime functionalizations, and the preparation of new classes of organic species, in particular, a wide variety of heterocyclic systems spanning small 3-membered ring systems to macroheterocycles. This consideration gives a general outlook of reaction routes, mechanisms, and driving forces and underlines the potential of metal-involving conversions of oxime species for application in various fields of chemistry and draws attention to the emerging putative targets.

show abstract

Section: Chemical Reviewsmentioning

confidence: 99%

Metal-Involving Synthesis and Reactions of Oximes

et al. 2017

Self Cite

View full text Add to dashboard Cite

show abstract

“…Imides are very important organic ligands due to their multiple applications namely in organic synthesis for the production of plastics, fungicides, pigments and pharmaceuticals. 1 In addition, their transition metal complexes are of potential interest, e.g. in catalysis, luminescence, medicinal chemistry and magnetism.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, an octahedral Ni(II) phthalimide derivative containing ethylenediamine moieties has been reported. 1 Thus the body of literature on the synthesis, isolation and structures of ligated nickel imidate complexes has been too limited to understand the relationships between the identity of the ligands and the patterns of reactivity. Here, we report the synthesis of nickel imidate complexes containing macrocyclic ancillary ligands, as well as the structure determinations of these species in the solid state and solution phase.…”

Section: Introductionmentioning

confidence: 99%

“…These coordination modes in 3a and 3b have been authenticated by X-ray crystal structure determination (vide infra). 1 H NMR spectroscopy has shown to be a powerful tool for the characterisation of five-coordinate nickel(II) complexes. 18 The 1 H NMR spectra of the complexes exhibit relatively well-resolved sharp resonances that have a chemical shift range which spans over 350 ppm.…”

Section: Introductionmentioning

confidence: 99%

“…Positive MS: m/z 465 (M + , 57%). IR n max /cm -1 3603, 3254, 1655, 1611, 1572, 1299, 1156, 1122, 950, 842, 603, 558 1. H NMR ((CD 3 ) 2 CO, 300 MHz): d 308.5 (H a ), 268.4 (H a ), 229.5 (H a ), 200.6 (H a ), 139.3 (9-Me, 3H), 85.5 (H a , 2H), 62.3 (4-Me, 3H), 36.2 (H a ), 29.5 (H a ), 20.5 (4-Me, 3H), 10.3 (H-sac), 9.4 (H-sac, 2H), 8.5 (H-sac), 5.8 (H 2 O), -9.6 (H b ), -11.5 (H b ), -13.1 (H b ), -18.5 (2-Me, 3H), -25.6 (H b ), -31.6 (H b ), -36.9 (H b ).…”

mentioning

confidence: 99%

See 2 more Smart Citations

Mono- and bidentate imidates of five-coordinate nickel(ii) with macrocyclic ligands: spectroscopic and photophysical properties

et al. 2010

View full text Add to dashboard Cite

The hydroxo-complexes [Ni(2)(mcN(3))(2)(mu-OH)](2)(PF(6))(2)] [mcN(3) = 2,4,4-trimethyl-1,5,9-triazacyclododec-1-ene (Me(3)-mcN(3)) or 2,4,4,9-tetramethyl-1,5,9-triazacyclododec-1-ene (Me(4)-mcN(3))] react with imides (Him) in 1 : 2 (succinimide, glutarimide, saccharine and 1,8-naphthalimide) or 1 : 1 (pyromellitic diimide) molar ratio, leading to the formation of the imidate complexes: [Ni(mcN(3))(H(2)O)(Im)](+) (Im = succi, gluti, sac), [Ni(mcN(3))(naphthi)](+) and [Ni(mcN(3))(H(2)O)](2)(mu-pyrdi)](2+). The single crystal structures of [Ni(Me(3)-mcN(3))(H(2)O)(sac)](PF(6)) (3a) and [Ni(Me(4)-mcN(3))(H(2)O)(sac)](sac) (3b) show that, in 3a, sac exhibits a N-monodentate coordination mode, while in 3b the coordination is through oxygen. X-Ray structure of [Ni(Me(4)-mcN(3))(naphthi)](PF(6)) (4b) shows N,O-bonded 1,8-naphthalimidate ligand. The VT (1)H NMR study, carried out on this complex, suggests that the rotation around the Ni-N bond is hindered by ca. 11.6 kcal mol(-1). These species exhibit blue luminescence which arises from a mixed MLCT and LC excited state, and these properties may be useful for structural predictions in the solid state of complexes for which crystal structures have not been established.

show abstract

1,3,5‐Triazapentadiene Nickel(II) Complexes Derived from a Ketoxime‐Mediated Single‐Pot Transformation of Nitriles

Kopylovich¹,

Kirillov²,

Tronova

et al. 2010

Eur J Inorg Chem

Self Cite

View full text Add to dashboard Cite

A series of cationic (2+) [Ni{HN=C(R)NHC(R)=NH}2](X)2 {R = 4‐(Cl)C6H4 (1), 3‐(NC)C6H4 (3), 4‐(NC)C6H4 (4) and Me (7); X = Cl– (1, 3, 4) or MeCOO–·H2O (7)} and neutral [Ni{HN=C(R)NC(R)=NH}2](solvate) {R = 3‐(Cl)‐4‐py (2), 3‐py (5) and 4‐py (6); solvate = MeOH and/or H2O; py = pyridyl} N,N‐chelating bis(1,3,5‐triazapentadiene/ato)nickel(II) [Ni(tap)2]2+/0 complexes has been easily generated by a ketoxime‐mediated single‐pot reaction of a nickel(II) salt [NiCl2·2H2O or Ni(MeCOO)2·4H2O] with 4‐chlorobenzonitrile, isophthalonitrile, terephthalonitrile, acetonitrile, 2‐chloro‐4‐cyanopyridine, 3‐cyanopyridine or 4‐cyanopyridine, respectively. The obtained compounds have been characterized by IR, 1H and 13C{1H} NMR spectroscopy, FAB‐MS(+) or ESI‐MS(+), elemental analyses and single‐crystal X‐ray diffraction [for 7 and solvated mono‐ {1a·(Me2CO)0.33·(MeOH)0.67} and bis‐deprotonated (2b·2Me2CO, 4b·CHCl3, 5b·Me2CO and 6b·MeOH) products, formed upon recrystallization of 1, 2, 4, 5 and 6, respectively]. The crystal structures of all compounds bear similar monomeric Ni(tap)2 units with a nearly square‐planar geometry. In addition, the structure of 7 features the formation of infinite 1D zig‐zag water–acetate chains {[(H2O)2(MeCOO)2]2–}n, which multiply interact with the [Ni(tap)2]2+ cations to generate a 2D hydrogen‐bonded supramolecular assembly.

show abstract

Novel nickel(II) complex bearing phthalimido ligands derived from oxime-mediated transformation of phthalonitrile

Cited by 10 publications

References 21 publications

Metal-Involving Synthesis and Reactions of Oximes

Metal-Involving Synthesis and Reactions of Oximes

Mono- and bidentate imidates of five-coordinate nickel(ii) with macrocyclic ligands: spectroscopic and photophysical properties

1,3,5‐Triazapentadiene Nickel(II) Complexes Derived from a Ketoxime‐Mediated Single‐Pot Transformation of Nitriles

Contact Info

Product

Resources

About