Methyl, ethyl, isopropyl and tert-butyl 3-oxo-2-(triphenylphosphoranyl-idene)butyrates, a common pattern for a preferred conformation

Castañeda F.; Terraza, C. A.; Garland M.T.; Bunton C.A.; Baggio R.F.

Keywords: dynamics, crystal, bond, structure, stress, methyl, torsion, bonds, interactions, molecular, organic, conformations, butyrate, electronic, angle, lengths, ethyl, compounds, chemical, atomic, Torsional, Intramolecular, isopropyl, dilocalization, oxotriphenylphosphoranylidene, oxotriphenyl, phosphoranylidene, Tertbutyl

Abstract

The crystal structures of four alkyl 3-oxo-2-(triphenyl-phosphoranylidene)butyrates, where the alkyl group is methyl (C 23H 21O 3P·0.5C 6H 6), (II), ethyl (C 24H 23O 3P), (III), isopropyl (C 25H 25O 3P), (IV), or tert-butyl (C 26H 27O 3P), (V), shows all of them to have the same conformation. They present a tetrahedral P atom and an sp 2 ylidic C atom, with the carbonyl groups adopting anti conformations with respect to the keto groups located close to the P atom. P-C-C-O torsion angles, bond lengths and angles indicate an effective electronic delocalization toward the keto groups. In each case, one H atom of the alkoxy group is close to one of the phenyl rings. These preferred conformations are evaluated as the result of attractive and repulsive intramolecular interactions.

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Título de la Revista: ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS
Volumen: 57
Número: 2
Editorial: WILEY-BLACKWELL PUBLISHING, INC
Fecha de publicación: 2001
Página de inicio: 180
Página final: 184
URL: http://www.scopus.com/inward/record.url?eid=2-s2.0-0142228931&partnerID=q2rCbXpz