acetylene chermistry by F. Diederich, P. J. Stang, R. R. Tykwinski

By F. Diederich, P. J. Stang, R. R. Tykwinski

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19) (or “carbo-methane” [4]) have been reported by Feldman [195]. On the basis of Mulliken charges and substituent electronegativity effect analyses, Schaefer III et al. 20 â), thus giving an apparent contracted CspaCsp bond length. This experimentally determined shortening is also not reproduced by semiempirical calculations (PM3, AM1, MNDO) [197]. The weak strain of the molecule was also estimated through the homodesmotic reaction: 4 CH3 -CaCH p C(CaCH)4 + 3 CH4, DHh(MP2) = 5 kcal mol–1. 19) is even lower.

The preceding Hçckel MO analysis was limited to out-of-plane pz orbitals. A similar treatment can be applied to the homoconjugated in-plane pxy orbitals [162], where the fictitious linear references are now “skipped” polyynes H(CaCCH2)NH. 01 kcal mol–1. Though formally positive, this value, and the corresponding energetic in-plane homoaromaticity, are negligible. – Homodesmotic ASE. Cyclizing homodesmotic reactions [170] are commonly employed to evaluate the energetic aromaticity of highly symmetrical annulene-type rings made up of alternating single and double bonds only [165, 166].

Despite their higher theoretical stability, the carbon rings remain experimentally elusive under the high-temperature conditions (i 2000hC) at which gaseous carbon clusters are produced. The open chains are indeed entropically favored through the possibility of large-amplitude motions [17]. The temperature-dependent rate constants for the cyclization and the ring snapping of C8, C10, and C12 were thus calculated within the rotor-harmonic oscillator approximation at the B3LYP/6-311G* level [182].

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