PMID: 11902907Mar 21, 2002Paper

Stereoelectronic effects and general trends in hyperconjugative acceptor ability of sigma bonds

Journal of the American Chemical Society
Igor V Alabugin, Tarek A Zeidan

Abstract

A systematic study of general trends in sigma acceptor properties of C-X bonds where X is a main group element from groups IVa-IIa is presented. The acceptor ability of the C-X sigma bonds in monosubstituted ethanes increases when going to the end of a period and down a group. Enhancement of acceptor ability of C-X sigma bonds as one moves from left to right in periods parallels the increase in electronegativity of X, whereas augmentation of acceptor ability in groups is opposite to the changes in electronegativity of X and in the C-X bond polarization, following instead the decrease in the energy of sigma(C)(-)(X) orbitals when one moves from the top to the bottom within a group. This simple picture of acceptor ability of sigma bonds being controlled by electronegativity in periods and by sigma orbital energy in groups is changed in monosubstituted ethenes where the role of electronegativity of the substituent X becomes more important due to increased overlap between sigma orbitals. The combination of several effects of similar magnitude influences acceptor ability of sigma bonds in monosubstituted ethenes in a complex way. As a result, the acceptor ability of sigma bonds can be significantly modified by substitution and is co...Continue Reading

References

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Citations

Nov 11, 2011·Journal of Molecular Modeling·Rosana M LobayanArturo Vitale
Nov 15, 2012·Journal of Molecular Modeling·Rosana M LobayanArturo Vitale
Aug 5, 2010·Journal of the American Chemical Society·Matthew D ShouldersRonald T Raines
May 19, 2012·Journal of the American Chemical Society·Kerry GilmoreIgor V Alabugin
Oct 3, 2012·The Journal of Organic Chemistry·Kyle T GreenwayB Mario Pinto
Aug 23, 2011·The Journal of Physical Chemistry. a·Therèse Zeegers-Huyskens, Eugene S Kryachko
Apr 4, 2013·The Journal of Physical Chemistry. a·Dipankar SutradharAsit K Chandra
Mar 9, 2011·Physical Chemistry Chemical Physics : PCCP·Alberto LesarriJens-Uwe Grabow
Sep 28, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Benjamin L Harris, Jonathan M White
Mar 31, 2016·Journal of Chemical Information and Modeling·Zhaomin LiuNicolas Moitessier
Jun 30, 2015·Tetrahedron Letters·Ping LuFraser F Fleming
Jan 14, 2016·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Aamer SaeedMauricio F Erben
Nov 25, 2017·Organic & Biomolecular Chemistry·Amani AlhifthiSpencer J Williams
Jun 12, 2008·Chemistry : a European Journal·Matthias D'hoogheNorbert De Kimpe
Aug 29, 2014·Chemistry : a European Journal·Jun Zhang, Michael Dolg
Aug 9, 2018·Physical Chemistry Chemical Physics : PCCP·Shilpa R Nath, Kaustubh A Joshi
May 29, 2007·ChemMedChem·Martin MorgenthalerKlaus Müller
Apr 14, 2005·Organic & Biomolecular Chemistry·Anette GregersenMikael Bols
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Jul 31, 2019·Free Radical Research·S Mohamad Reza NazifiKrzysztof K Zborowski

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