Quantification of the push-pull Effect in disubstituted alkynes - Application of occupation quotients pi*/pi and C-13 chemical shift differences Delta delta(C C)

  • Structures, C-13 chemical shifts, and the occupation quotients of anti-bonding pi* and bonding pi orbitals of the C C triple bond along a series of push-pull alkynes (p)X-C6H4 C(O)-C C-NH-C6H4-Y(P) (X,Y= H, Me, OMe, NMe2, NO2, COMe, COOMe, F, Cl, Br) were computed at the DFT level (B3LYP/6-311G**) of theory. Both the stereochemistry (cis/trans-isomers) by steric twist and the push-pull character by both C-13 chemical shift differences (Delta delta(C C)) and the occupation quotient (pi(C C)/pi(C C)) were studied; the latter two parameters can be readily employed to precisely quantify the push-pull effect in alkynes. (C) 2014 Elsevier B.V. All rights reserved.

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Author:Erich Kleinpeter, Ute Klaumuenzer
ISSN:0022-2860 (print)
ISSN:1872-8014 (online)
Parent Title (English):Journal of molecular structure
Place of publication:Amsterdam
Document Type:Article
Year of first Publication:2014
Year of Completion:2014
Release Date:2017/03/27
Tag:C-13 chemical shift difference Delta delta(C C); Occupation quotient pi*/pi; Push-pull alkynes; Push-pull effect; Steric hindrance
First Page:193
Last Page:195
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert