Article Dans Une Revue Journal of Molecular Structure Année : 2003

Structure and reactivity of cycloimmonium ylides. Theoretical study in triazolium ylides by AM1, PM3 and DFT procedure methods

Résumé

This paper reports some general remarks on structure and reactivity of monosubstituted and disubstituted cycloimmonium ylides. The results have been achieved by calculations on ylide bond lengths, bond orders, dipolar moments and rotational barriers. Some aspects have been followed on charges and high-occupied molecular orbital coefficients of ylide carbon atoms during rotation around ylide bond. The AM1, PM3 and DFT procedure methods have been used in this study. Three ylidic systems have been selected as models of cycloimmonium ylides: (a) 1-ethoxycarbonylmethyl 1,2,4-triazol-1-ium 4′-nitrobenzoyl 2″,4″,6″-trinitrophenyl methylides, (b) 4-phenylbenzoyl 1,2,4-triazol-1-ium methylide and (c) 4-phenyl dibenzoyl 1,2,4-triazol-1-ium methylide. DFT and AM1 procedure methods are appropriate for the description of monosubstituted cycloimmonium ylides. Only DFT procedure method is recommended for the description of the non-planar disubstituted cycloimmonium ylides. The resonance interaction in planar monosubstituted and planar disubstituted cycloimmonium ylide systems permits to carry out 3+2 cycloadditions preferably in non or less polar solvents.

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Dates et versions

hal-04442748 , version 1 (06-02-2024)

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Georgiana Surpateanu, François Delattre, Patrice Woisel, Gérard Vergoten, Gheorghe Surpateanu. Structure and reactivity of cycloimmonium ylides. Theoretical study in triazolium ylides by AM1, PM3 and DFT procedure methods. Journal of Molecular Structure, 2003, 645 (1), pp.29-36. ⟨10.1016/S0022-2860(02)00488-X⟩. ⟨hal-04442748⟩
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