3-(Aminomethylene)pentane-2,4-dione

Gróf, Martin; Milata, Viktor; Kožı́šek, Jozef

doi:10.1107/s1600536806035276

Cited by 4 publications

(3 citation statements)

References 3 publications

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“…The Schiff base exists in its enamine tautomeric form with a formal double bond between the carbon atoms C3 and C6 (CÀ C: 145.2(1) pm). Similar enamine motifs have been observed in the related compounds Software programs used OLEX2, [21] SHELX, [22] PLATON, [23] Diamond [24] 3-(aminomethylene)pentane-2,4-dione, [16] 3-(methylaminomethylene)pentane-2,4-dione, [17] and the Schiff base condensation products of 3-formylacetylacetone and α-aminoacids. [3] The hydrogen atom H22 attached to the nitrogen atom acts as donor in an intramolecular NÀ H•••O hydrogen bridge with S 1 1 (6) topology.…”

Section: Schiff Base Hl (2)mentioning

confidence: 57%

Synthesis and Coordination Behaviour of a Novel Tridentate P,N,O‐Ketiminate Ligand

Merzweiler¹,

Halz²,

Hentsch³

et al. 2021

Zeitschrift anorg allge chemie

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Treatment of o-(diphenylphosphino)aniline with 3-formylacetylacetone led to the formation of the ketimine type Schiff base 3-((o-diphenylphosphino-phenylamino)-methylene)-pentane-2,4-dione (oÀ PPh 2 À C 6 H 4 À NHÀ CH=C(COCH 3 ) 2 , HL). Complexes [ML 2 ] (M = Fe, Co, Ni, Cu) were obtained from the reaction of HL with the corresponding metal acetate or acetylacetonate derivatives. The [ML 2 ] complexes (M = Fe, Co, Ni) exhibit a distorted octahedral coordination from two tridentate P,N,O ketiminate ligands L À . The arrangement of the ligands is meridional in the case of [FeL 2 ] and [NiL 2 ] . The cobalt complex [CoL 2 ] displays a facial coordination. In the case of the nearly square planar copper complex [CuL 2 ], only the ketiminate functionalities of the ligands are involved in coordination and the participation of the PPh 2 groups is neglectable.

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Section: Schiff Base Hl (2)mentioning

confidence: 57%

Synthesis and Coordination Behaviour of a Novel Tridentate P,N,O‐Ketiminate Ligand

Merzweiler¹,

Halz²,

Hentsch³

et al. 2021

Zeitschrift anorg allge chemie

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“…Ein charakteristisches Merkmal der Molekülstruktur von 1 ist eine intramolekulare Wasserstoffbrücke des Typs S 1 1 (6)9 zwischen der NH‐Funktion der Enamineinheit und dem Carbonylsauerstoffatom O2 des Pentandionfragmentes [N ··· O: 260, 7(2) pm]. Eine ähnliche Konstitution mit intramolekularer N–H ··· O‐Brücke [N ··· O: 262, 7(2) pm] wird auch in der Stammverbindung 3‐(Aminomethylen)pentan‐2, 4‐dion gefunden 10. Die Anordnung der Moleküle im Kristall wird im Wesentlichen durch intermolekulare Wasserstoffbrücken bestimmt, in denen die Hydroxylgruppe der Carbonsäure (O4–H13) als H‐Donor und das Carbonylsauerstoffatom O1 der Pentandioneinheit als Akzeptor auftritt [Typ C 1 1 (9)].…”

Section: Ergebnisse Und Diskussionunclassified

“…Eine ähnliche Konstitution mit intramolekularer N- 7(2) pm] wird auch in der Stammverbindung 3-(Aminomethylen)pentan-2,4-dion gefunden. [10] Die Anordnung der Moleküle im Kristall wird im Wesentlichen durch intermolekulare Wasserstoffbrücken bestimmt, in denen die Hydroxylgruppe der Carbonsäure (O4-H13) als H-Donor und das Carbonylsauerstoffatom O1 der Pentandioneinheit als Akzeptor auftritt [Typ C 1 1 (9)]. Dies führt zu helicalen Ketten, die sich entlang der kristallographischen 4 1 -Schraubenachse in c-Richtung anordnen (Abbildung 2).…”

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Synthese und Koordinationsverhalten neuer Schiffscher Basen aus 3‐Formylacetylaceton und natürlichen L‐Aminosäuren

Hentsch

Wagner

Merzweiler

2014

Zeitschrift anorg allge chemie

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Three novel chiral Schiff Base ligands (H2L) were prepared from the condensation reaction of 3‐formyl acetylacetone with the amino acids L‐alanine, L‐phenylalanine, and L‐threonine. X‐ray single crystal analyses revealed that the Schiff Base compounds exist as enamine tautomers in the solid state. The molecular structure of the compounds is stabilized by an intramolecular hydrogen bridge between the enamine NH function and a carbonyl oxygen atom of the pentandione residue. Treatment of the ligands H2L with copper(II) actetate in the presence of pyridine led to the formation of copper complexes [CuL(py)]. In each of the complexes the copper atoms adopt a distorted square‐pyramidal coordination. Three of the basal coordination sites are occupied by the doubly deprotonated Schiff Bases L2– which act as tridentate chelating O, N, O‐ligands. The remaining coordination sites are occupied by a pyridine ligand at the base and a carboxyl oxygen atom of a neighboring complex at the apical position. The latter coordination is responsible for a catenation of the complexes in the solid state.

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Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone ando-,m- andp-aminobenzoic acid

Halz¹,

Hentsch²,

Wagner³

et al. 2022

Acta Cryst E

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Treatment of 3-formylacetylacetone with the isomeric o-, m- and p-aminobenzoic acids led to the formation of the corresponding Schiff bases, namely, 3-[(2-carboxyphenylamino)methylidene]pentane-2,4-dione, 1, 3-[(3-carboxyphenylamino)methylidene]pentane-2,4-dione, 2, and 3-[(4-carboxyphenylamino)methylidene]pentane-2,4-dione, 3, all C13H13NO4, that contain a planar amino-methylene-pentane-2,4-dione core with a strong intramolecular N—H...O hydrogen bridge. The carboxyphenyl groups attached to the nitrogen atom are almost coplanar to the central molecular fragment. Depending on the position of the carboxyl unit, different supramolecular structures with hydrogen-bonding networks are formed in the three title structures.

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3-(Aminomethylene)pentane-2,4-dione

Abstract: Key indicatorsSingle-crystal X-ray study T = 100 K Mean (C-C) = 0.002 Å R factor = 0.037 wR factor = 0.102 Data-to-parameter ratio = 17.5For details of how these key indicators were automatically derived from the article, see

Cited by 4 publications

References 3 publications

Synthesis and Coordination Behaviour of a Novel Tridentate P,N,O‐Ketiminate Ligand

Synthesis and Coordination Behaviour of a Novel Tridentate P,N,O‐Ketiminate Ligand

Synthese und Koordinationsverhalten neuer Schiffscher Basen aus 3‐Formylacetylaceton und natürlichen L‐Aminosäuren

Synthesis and crystal structures of three Schiff bases derived from 3-formylacetylacetone ando-,m- andp-aminobenzoic acid

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