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Hidden Dicarbene Nature of Acetylenes and Captodative Bonding on Carbon.

DFT derived molecular electrostatic potential (MESP), ¹³C NMR chemical shift (δ), bond order and coordination reactions show that alkynes (RCCR) attain 1,2-dicarbene nature during CCR angle bending. Alkyne carbon atoms of bent structures exhibit MESP features unique to lone-pair bearing atoms, δ around 200 ppm typical for carbene centers and large reduction in CC triple bond character. Lone pair bearing atoms of R substituents enhance the carbene character. The bent alkynes can be trapped with Lewis acids (BH₃, BF₃, AlF₃ and AlCl₃) as the lone pairs developed on carbon centers provide strong donor type dative bonding. The dative bond gives a formal valence electron count six on carbon and suggests the for-mation of acceptor type dative bonding to carbon from Lewis base (NH₃). Reaction of alkynes with (Lewis acid-Lewis base) systems yield (Lewis acid)₂-Alkyne-Lewis base)₂ complexes which are exothermic and exergonic for many cases. These complexes are examples of captodative carbon(II) compounds.