L-shaped three-center two-electron (C-C-C)+ bonding array

Naohiko Yoshikai, Salai Cheettu Ammal, Eiichi Nakamura

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)


The structures and reactivities of the complexes between carbenium ions (R+) and acetylene or propyne have been investigated with the aid of electron-correlated quantum mechanical calculations (hybrid density functional, perturbation theory, and coupled cluster methods). Depending on the R group, the acetylene/carbenium ion interaction can produce either an "open" 3c-2e structure or the conventional vinyl cation structure. The "open" 3c-2e C-C-C bonding geometry exists as a minimum for R = methyl and primary/secondary/tertiary alkyl, and hence is the most notable. The alignment of three carbon centers is neither bridged nor linear, but L-shaped, and represents a new type of "open" 3c-2e bonding that has so far escaped proper attention.

Original languageEnglish
Pages (from-to)12941-12948
Number of pages8
JournalJournal of the American Chemical Society
Issue number40
Publication statusPublished - 2004 Oct 13


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