Abstract
Natural bond orbital (NBO) analysis method was performed for the investigation of the relative stability and the nature of the highly strained central bond in [1.1.1]propellane and some [1.1.1]heteropropellane compounds. The results explained that how the p character of natural atomic hybrid orbital on C1 and C3 (central bond) is increased by the substitution of the bridge head CH 2 groups by O, NH, or S and also the resulting bent of the carbon natural hybrid orbitals (NHOs) of the σ CX and σ CZ bond orbital from the lines of C–X and C–Z centers, in these compounds. The NBO analysis of donor–acceptor (bond–antibond) interactions resulted in decreasing of occupancy of the localized σ C1C3 orbital of the idealized Lewis structure, increasing of occupancy of σ ∗ C1C3 of the non-Lewis orbital, and also their subsequent impact on molecular stability and geometry (bond length) along with the resulting p character of the corresponding carbon NHO of σ bond orbital. Actually, the results suggested that in these compounds, the C1–C3 bond lengths are closely controlled by the p character of these hybrid orbitals and also by the nature of CX bonds. The magnitude of the molecular stabilization energy associated to delocalization from σ C1C3 and to σ C1C3 ∗ bond orbital were also quantitatively determined.
Published Version
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