Org Chem Acidity and Basicity Structural Effects

Embed Size (px)

Citation preview

  • 8/19/2019 Org Chem Acidity and Basicity Structural Effects

    1/3

    Resonance effect - when we can draw two (or more) forms of the same molecule that differ 

    only in the placement of their electrons. Resonance usually reduces basicity. Why?

    Resonancedelocalizeselectrondensityfromtheatomthatwantstoshareitselectrons,  which leadsto

    thestructurebeingaweakerbasestrongercon!ugateacid.

    "nducti#e $ffect: %heeffectonelectrondensityinoneportionofamoleculeduetoelectron

    withdrawingorelectrondonatinggroupselsewhereinthemolecule.

    Inductiveeffectdependsonthefollowing:

    1. Electronegativityofthegroup Fluorinewithdrawsmoreelectrondensityfromneighboring

    atomstowardsitselfthanHydrogenwould. =lowerbasicity(smaller pa!.

     ". #umberofelectronwithdrawingorelectrondonatinggroups $hegreaterthenumberof 

    electronwithdrawinggroups%$hesmallerthenumberof electrondonating groups =lowerbasicity(smaller pa!.

    &. 'istancefromthegroup $hesmallerthedistancefromtheelectronwithdrawinggroup%$he

    greaterthedistancefromthe electrondonatinggroup =lowerbasicity(smaller pa!

  • 8/19/2019 Org Chem Acidity and Basicity Structural Effects

    2/3

    &ypercon!ugation - %his is #ery similar to resonance, sometimes referred to a 'o-bond

    resonance or aker-'athan effect. "n case of classical resonance we had seen the

    in#ol#ement of lone pair of electrons and pi bonds (doubletriple bonds). "n

    hypercon!ugation single bonds are in#ol#ed in the electron delocalization circuitry. %his

    effect is still not fully understood in detail but would ser#e the purpose of basic organic

    chemistry.

    teric effect - two or more groups or atoms come in close pro*imity to each other

    (precisely within each other+s #an der Waals radii (definition of #an der Waals radii can

    be found in any standard te*tbook)) and result in a mutual repulsion.

  • 8/19/2019 Org Chem Acidity and Basicity Structural Effects

    3/3

    &ydrogen bond - a weak type of force that forms a special type of dipole-dipole

    attraction which occurs when a hydrogen atom bonded to a strongly electronegati#e

    atom e*ists in the #icinity of another electronegati#e atom with a lone pair of electrons.

    %hese bonds are generally stronger than ordinary dipole-dipole and dispersion forces,

    but weaker than true co#alent and ionic bonds.