Synthesis and Crystal Structures of N,N′-Disubstituted Piperazines

Safko, Jason P.; Pike, Robert D.

doi:10.1007/s10870-012-0346-1

Cited by 4 publications

(1 citation statement)

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“…Most of the crystallographically characterized diarylpiperazines feature the chair conformation; a few have been determined in the twist-boat form (Wirth et al, 2012). Whereas the phenyl groups of piperazine 2 are twisted relative to the N 2 C 4 mean plane, the structure of the less substituted N,N 0 -diphenylpiperazine, which crystallizes in the Pbca space group, exhibits phenyl groups closer to being in conjugation with the nitrogen lone pairs (Wirth et al, 2012;Safko & Pike, 2012). The sum of the bond angles around nitrogen is quite similar between the two structures (2: 338-341 ; N,N 0 -diphenylpiperazine: 343 ), though the N-C aryl bond lengths are slightly shortened in the phenyl-substituted analogue [2: 1.426 (3)-1.431 (3) Å ; N,N 0 -diphenylpiperazine: 1.4157 (15) Å ], indicating that resonance delocalization is a perhaps a minor effect, if present, while packing effects likely dominate.…”

Section: Database Surveymentioning

confidence: 99%

A structural study of 2,4-dimethylaniline derivatives

2018

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Section: Database Surveymentioning

confidence: 99%

A structural study of 2,4-dimethylaniline derivatives

2018

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Synthesis, biological evaluation and molecular modeling studies of phenyl-/benzhydrylpiperazine derivatives as potential MAO inhibitors

Kumar

Sheetal

Mantha

et al. 2018

Bioorganic Chemistry

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Network formation and photoluminescence in copper(i) halide complexes with substituted piperazine ligands

et al. 2012

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The synthesis, X-ray structures and photophysics of ten complexes of CuX (X = I or Br) with bridging N-substituted and N,N'-disubstituted piperazines (Pip) are presented. Depending on the steric demand of the Pip substituents, the complexes fall into four categories: (CuX)(4)(Pip)(2), which are networks of linked Cu(4)X(4) cubane units, (CuX)(2)(Pip), which are chains of linked Cu(2)X(2) rhombs, and (CuX)(2)(Pip)(2) or (CuX)(4)(Pip)(4), which are simple rhomboid dimers and cubane tetramers. A combination of spectroscopic studies and DFT calculations was used to investigate the luminescence of the products. The results suggest that the relatively high energy emission seen in dimers is due to cluster-centred (XMLT/metal-centred) excitations for the aliphatic amines and MLCT (d →π*) for aromatic amines, and low energy emission seen in the tetramers is the result of cluster-centred transitions. The (CuI)(2)(Pip) complexes act as sensor materials, undergoing irreversible reaction with aliphatic and aromatic amines (Nu) in the vapour state, irreversibly producing cubanes (CuI)(4)Nu(4), with corresponding production of long wavelength emission.

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Synthesis and Crystal Structures of N,N′-Disubstituted Piperazines

Cited by 4 publications

References 40 publications

A structural study of 2,4-dimethylaniline derivatives

A structural study of 2,4-dimethylaniline derivatives

Synthesis, biological evaluation and molecular modeling studies of phenyl-/benzhydrylpiperazine derivatives as potential MAO inhibitors

Network formation and photoluminescence in copper(i) halide complexes with substituted piperazine ligands

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