Crystal Structure of 1,2,4,1',2',4'-Hexamethylferrocene

Ibrahimova, N.Z.; Jafarov, G.M.; Taghiev, D. B.; Lyatifov, I.R.

doi:10.1134/s1070328420010029

Cited by 3 publications

(4 citation statements)

References 21 publications

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“…hexamethylferriciniumhexafluorophosphate salt (sym. Ме 6 Fc + PF 6 -) obtained by us [7,8] were analyzed comparatively with the appropriate structural parameters of the salts of octa-and decamethylferricinium cations ([Ме n Fc + X -, n = 8, 10; X -= PF 6 -, BF 4 -, Br 3 -] known from references to investigate the presence of hydrogen bonds in the sym. Ме 6 Fc + PF 6 complex.…”

Section: Resultsmentioning

confidence: 99%

“…The conditions of growing single crystals of sym. Ме6Fc complex and the conducted experiment and obtained structural data by the method of X-ray structural analysis are reflected in our previous works [7,8].…”

Section: Experimental Partmentioning

confidence: 95%

“…polymethylferrocene/sym. polymethylferricinium (Ме n Fc/ Ме n Fc + , n = 6, 8, 10) redox systems [7][8][9][10][11]. It created a need to comparatively study the crystal structures of the sym.…”

Section: Introductionmentioning

confidence: 99%

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HYROGEN BOND IN CRYSTAL STRUCTURE OF SALTS OF SYMMETRIC POLYMETHYLFERRICINIUM CATİONS (SYM.[(CH3)mC5H5–m]2Fe+X – , m=3,4,5 or МеnFc+X – , n = 6, 8, 10; X– = PF6 – , BF4 – , Br3 – )

Ibrahimova,

Rustemova,

Jafarov

et al. 2023

Chemical Problems

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The article explains reasons of elongation (0.019 Å) of the bond between iron–cyclopentadienyl ring in the 1,2,4,1,2,4-hexamethylferricinium (sym. Ме6Fc+ ) cation formed due to the one-electron oxidation of iron atom of sym.1,2,4,1,2,4-hexamethylferrocene (sym. Ме6Fc) molecule which is 2-2.5 times smaller (0.04–0.05 Å) than that observed in pairs of ferrocene/ferricinium (Fc/Fc+ ), sym. octamethylferrocene/sym.octamethylferricinium (Ме8Fc/Me8Fc+ ) and decamethylferrocene/decamethylferricinium (Ме10Fc/Ме10Fc+ ). For this purpose, X-ray structural parameters characterizing the interaction between cation and anion in the sym.Ме6Fc+PF6 – complex was compared with appropriate parameters in Ме8Fc+BF4 – , Ме10Fc+Br3 and Ме10Fc+PF6 – complexes; and it was mooted that there is an F …H type hydrogen bond in this complex taking into account the length of the non-valent F…H contact (bond) in the sym. Ме6Fc+PF6 – complex. The lengths of Р–F bonds and F–P–F angles of the PF6 – anion in the listed 4 sandwich complexes were compared with appropriate parameters in the РF6 – anion of the LiРF6 crystal. It has been unequivocally proved that F…H hydrogen bonds exist in the sym.Ме6Fc+PF6 – complex.

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Section: Resultsmentioning

confidence: 99%

Section: Experimental Partmentioning

confidence: 95%

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HYROGEN BOND IN CRYSTAL STRUCTURE OF SALTS OF SYMMETRIC POLYMETHYLFERRICINIUM CATİONS (SYM.[(CH3)mC5H5–m]2Fe+X – , m=3,4,5 or МеnFc+X – , n = 6, 8, 10; X– = PF6 – , BF4 – , Br3 – )

Ibrahimova,

Rustemova,

Jafarov

et al. 2023

Chemical Problems

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“…Although the solid-state structure of ( S , S P )- S - tert -butyl-2-methylferrocenesulfoxide ( S , S P -1d ) is similar to one reported by Kagan, it can be compared with the one of ( S , R P )- S - tert -butyl-2-iodoferrocenesulfoxide ( S , R P -1b ) as the two structures are very similar ( Figure 4 ). Indeed, the S=O bonds are slightly bended toward the iron, with similar C10-S1 and C9-S1 bond lengths while C6-I1 and C10-C11 were found to fall in the range of such bonds [ 87 , 88 ]. Furthermore, both ferrocene cores were found in a staggered conformation with a torsion angle C10-Cg1···Cg2-C3 of −12.70° for S , R P -1b (Cg1 being the centroid of the C6-C7-C8-C9-C10 ring and Cg2 being the centroid of the C1-C2-C3-C4-C5 ring) and a torsion angle C9-Cg1···Cg2-C1 of −8.92° for S , S P -1d (Cg1 bring the centroid of C6-C7-C8-C9-C10 ring and Cg2 being the centroid of C1-C2-C3-C4-C5 ring).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Polysubstituted Ferrocenesulfoxides

et al. 2022

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The purpose of the study is to design synthetic methodologies, especially directed deprotometalation using polar organometallic reagents, to access polysubstituted ferrocenesulfoxides. From enantiopure 2-substituted (SiMe3, PPh2) S-tert-butylferrocenesulfoxides, a third substituent was first introduced at the 5 position (SiMe3, I, D, C(OH)Ph2, Me, PPh2, CH2NMe2, F) and removal of the trimethylsilyl group then afforded 2-substituted ferrocenesulfoxides unreachable otherwise. Attempts to apply the “halogen dance” reaction to the ferrocenesulfoxide series led to unexpected results although rationalized in light of calculated pKa values. Further functionalizations were also possible. Thus, new enantiopure, planar chiral di- and trisubstituted ferrocenes have been obtained, in addition to several original 2-substituted, 2,3- and 2,5-disubstituted, 2,3,5-trisubstituted and even 2,3,4,5-tetrasubstituted ferrocenesulfoxides, also enantiopure.

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