1-Ferrocenyl-2-phenylethanedione

Glidewell, Christopher; Gottfried, Michael; Trotter, James; Ferguson, George

doi:10.1107/s0108270195015034

Cited by 5 publications

(4 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Glidewell et al found short CH/C(Cp) distances in 1-ferrocenyl-2-phenylethanedione and commented on the possibility of attractive CH/p bond 330 Cowley found a continuous CH/p-bonded structure between CH of the imidazolium ligand and the Cp moiety of a transition-metal complex. 331 Interactions between CH(Cp) and p(Cp) were reported to make up a persistent packing motif in diferrocenyldiselenide and diferrocenyldisulfide.…”

Section: Interactions Involving Cyclopentadienyl (Cp) P-systemsmentioning

confidence: 99%

CH/? hydrogen bonds in crystals

Nishio¹

2004

CrystEngComm

1,389

781

View full text Add to dashboard Cite

The nature and characteristics of the CH/p interaction are discussed by comparison with other weak molecular forces such as the CH/O and OH/p interaction. The CH/p interaction is a kind of hydrogen bond operating between a soft acid CH and a soft base p-system (double and triple bonds, C 6 and C 5 aromatic rings, heteroaromatics, convex surfaces of fullerenes and nanotubes). The consequences of CH/p hydrogen bonds in supramolecular chemistry are reviewed on grounds of recent crystallographic findings and database analyses. The topics include intramolecular interactions, crystal packing (organic and organometallic compounds), host/ guest complexes (cavity-type inclusion compounds of cyclodextrins and synthetic macrocyclic hosts such as calixarenes, catenanes, rotaxanes and pseudorotaxanes), lattice-inclusion type clathrates (including liquid crystals, porphyrin derivatives, cyclopentadienyl compounds and C 60 fullerenes), enantioselective clathrate formation, catalytic enantioface discriminating reactions and solid-state photoreaction. The implications of the CH/p concept for crystal engineering and drug design are evident.

show abstract

Section: Interactions Involving Cyclopentadienyl (Cp) P-systemsmentioning

confidence: 99%

CH/? hydrogen bonds in crystals

Nishio¹

2004

CrystEngComm

1,389

781

View full text Add to dashboard Cite

show abstract

“…This bond length can also be compared with the structurally related compounds in which the corresponding bond distances are 1.529 (5) and 1.542 (6) Å in 1-ferrocenyl-2- phenylethanedione [16] and 1,1 0 -ferrocenediylbis(2-phenylethanedione) [17], respectively. The C=O bond length (C7=O1 = 1.221 (3) Å ) has almost the same value as that observed in BZ and also in the analogous compounds (Table 3), and it is also close to the values observed in hexatert-butylbenzil (1.227 (4) Å ) [9], and in 1,2-bis(3-methyl-2-thienyl)ethane-1,2-dione (1.218 (4) Å ) [26].…”

Section: Resultsmentioning

confidence: 99%

“…The unusual crystal structures of BZ [9,11] and its optical properties [1] have stimulated several infrared studies [1]. Structurally similar compounds, namely 1-ferrocenyl-2-phenylethanedione [16] and ferrocene-1,1 0 -diylbis(2-phenylethanedione) [17] were reported. These two compounds crystallized in non-centro-symmetric space group P2 1 2 1 2 1 and P3 1 21, respectively, so that the molecules are chiral in the solid state.…”

mentioning

confidence: 99%

Structural and vibrational investigation of 1, 2-bis(3, 4-dimethoxyphenyl) ethane-1, 2-dione (Veratril): experimental and theoretical studies

et al. 2008

View full text Add to dashboard Cite

The molecular and crystal structures of 1,2-bis(3,4-dimethoxyphenyl)ethane-1,2-dione (TMBZ = tetramethoxybenzil) were determined by a single-crystal X-ray diffraction, 1 H NMR, and FT-IR spectroscopy. The compound TMBZ (C 18 H 18 O 6 , M r = 330.32) crystallized in the orthorhombic Fdd2 space group wherein: a = 39.145(4), b = 18.167(2), c = 4.3139(5) Å and b = 90°, Z = 8. The packing of the molecules in the crystal lattice is stabilized by intermolecular C-H_O contacts in the herringbone arrangement. The molecular geometry and harmonic frequencies of TMBZ in the ground state were calculated utilizing density functional (B3LYP) method with the 6-311++G(d, p)-basis set. The density functional theory optimized the geometric structure, and vibrational wave numbers of TMBZ in gas phase were compared with the experimental data. A complete assignment of the fundamentals was proposed based on the total energy distribution calculation.

show abstract

“…3). In 1-ferrocenyl-2-phenylethanedione, the C--H...O hydrogen bonding forms simple chains around a 21 axis (Glidewell, Gottfried, Ferguson & Trotter, 1996).…”

Section: C24 C25nomentioning

confidence: 99%