Distinction of Push,pull effect and steric hindrance in disubstituted alkynes

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Abstract

The push,pull effect in two series of disubstituted alkynes was studied at the DFT level [B3LYP/6-311G(d)] by application of the13C chemical shift differences (GIAO) between the alkyne carbon atoms (ΔδC{triple bond, long}C), the charge difference between these carbons (ΔqC{triple bond, long}C), the occupation quotient (NBO) of anti-bonding π*, and bonding π orbitals (π*C{triple bond, long}C/πC{triple bond, long}C) and the bond length (dC{triple bond, long}C) of the C{triple bond, long}C triple bond. The linear dependence of dC{triple bond, long}Cversus π*C{triple bond, long}C/πC{triple bond, long}Cquantifies changes in the push,pull effect while deviations from the latter correlation indicate and ascertain quantitatively to what extent steric hindrance restricts the strain-less conjugation of the C{triple bond, long}C triple bond π-orbitals in the disubstituted alkynes. © 2009 Elsevier Ltd. All rights reserved.

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Kleinpeter, E., & Frank, A. (2009). Distinction of Push,pull effect and steric hindrance in disubstituted alkynes. Tetrahedron, 65(22), 4418–4421. https://doi.org/10.1016/j.tet.2009.03.075

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