Selective synthesis of (3-ferrocenylprop-2-en-1-yl)triphenylphosphonium iodide: crystal structure determination of two polymorphs.
Identifieur interne : 000387 ( Main/Exploration ); précédent : 000386; suivant : 000388Selective synthesis of (3-ferrocenylprop-2-en-1-yl)triphenylphosphonium iodide: crystal structure determination of two polymorphs.
Auteurs : Rafika Bouchene [Algérie] ; Jean Claude Daran [France] ; Hocine Merazig [Algérie] ; Eric Manoury [France] ; Sofiane Bouacida [Algérie]Source :
- Acta crystallographica. Section C, Structural chemistry [ 2053-2296 ] ; 2017.
Abstract
This work is part of a project studying the reactivity of a new ferrocenyl allylammonium salt, [3-(trimethylazaniumyl)prop-1-en-1-yl]ferrocene iodide, (1+)·I-, with different nucleophiles. With nitrogen-based nucleophiles, different ferrocenyl allylamine isomers have been synthesized successfully in good yield. Optimization of the basicity of the reaction medium has allowed selection of the best operating conditions to obtain the targeted isomer. In a similar way and in order to introduce phosphorus-containing functional groups, the reaction of ammonium salt (1+)·I- with a phosphorus nucleophile, namely triphenylphosphane, was attempted. It was then possible to isolate single crystals of (3-ferrocenylprop-2-en-1-yl)triphenylphosphonium iodide, [Fe(C5H5)(C26H23P)]I, which is shown to crystallize in two concomitant polymorphic forms, viz. a triclinic form, (I), in the space group P-1, and a monoclinic form, (II), in the space group P21/c. In the inter-ion packing of polymorph (I), the cations form bilayer ribbons via C-H...π and π-π stacking interactions. In polymorph (II), where π-π interactions do not occur, adjacent molecules are joined by C-H...π interactions into a one-dimensional helical arrangement along the b axis.
DOI: 10.1107/S2053229617004867
PubMed: 28469063
Affiliations:
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Bouaghi</wicri:noRegion></affiliation></author></analytic><series><title level="j">Acta crystallographica. Section C, Structural chemistry</title><idno type="eISSN">2053-2296</idno><imprint><date when="2017" type="published">2017</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">This work is part of a project studying the reactivity of a new ferrocenyl allylammonium salt, [3-(trimethylazaniumyl)prop-1-en-1-yl]ferrocene iodide, (1<sup>+</sup>)·I<sup>-</sup>, with different nucleophiles. With nitrogen-based nucleophiles, different ferrocenyl allylamine isomers have been synthesized successfully in good yield. Optimization of the basicity of the reaction medium has allowed selection of the best operating conditions to obtain the targeted isomer. In a similar way and in order to introduce phosphorus-containing functional groups, the reaction of ammonium salt (1<sup>+</sup>)·I<sup>-</sup> with a phosphorus nucleophile, namely triphenylphosphane, was attempted. It was then possible to isolate single crystals of (3-ferrocenylprop-2-en-1-yl)triphenylphosphonium iodide, [Fe(C<sub>5</sub>H<sub>5</sub>)(C<sub>26</sub>H<sub>23</sub>P)]I, which is shown to crystallize in two concomitant polymorphic forms, viz. a triclinic form, (I), in the space group P-1, and a monoclinic form, (II), in the space group P2<sub>1</sub>/c. In the inter-ion packing of polymorph (I), the cations form bilayer ribbons via C-H...π and π-π stacking interactions. In polymorph (II), where π-π interactions do not occur, adjacent molecules are joined by C-H...π interactions into a one-dimensional helical arrangement along the b axis.</div></front></TEI><affiliations><list><country><li>Algérie</li><li>France</li></country><region><li>Midi-Pyrénées</li><li>Occitanie (région administrative)</li></region><settlement><li>Toulouse</li></settlement></list><tree><country name="Algérie"><noRegion><name sortKey="Bouchene, Rafika" sort="Bouchene, Rafika" uniqKey="Bouchene R" first="Rafika" last="Bouchene">Rafika Bouchene</name></noRegion><name sortKey="Bouacida, Sofiane" sort="Bouacida, Sofiane" uniqKey="Bouacida S" first="Sofiane" last="Bouacida">Sofiane Bouacida</name><name sortKey="Merazig, Hocine" sort="Merazig, Hocine" uniqKey="Merazig H" first="Hocine" last="Merazig">Hocine Merazig</name></country><country name="France"><region name="Occitanie (région administrative)"><name sortKey="Daran, Jean Claude" sort="Daran, Jean Claude" uniqKey="Daran J" first="Jean Claude" last="Daran">Jean Claude Daran</name></region><name sortKey="Manoury, Eric" sort="Manoury, Eric" uniqKey="Manoury E" first="Eric" last="Manoury">Eric Manoury</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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