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    Tacticity

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    chemasim
    This document discusses the tacticity of polymers made from 1,2-disubstituted vinyl monomers. It defines three possible stereoregular patterns for these polymers: threo-diisotactic, erythro-diisotactic, and disyndiotactic. Isotactic polymers have the substituents on the same side of the polymer chain. Syndiotactic polymers have the substituents alternating sides. Diisotactic polymers have both substituents on the same side of adjacent monomers. Disyndiotactic polymers have the substituents alternating between threo and erythro arrangements on adjacent monomers. Newman projections are used to illustrate these different arrangements.

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    Tacticity

    Uploaded by

    chemasim
    375 views4 pages
    This document discusses the tacticity of polymers made from 1,2-disubstituted vinyl monomers. It defines three possible stereoregular patterns for these polymers: threo-diisotactic, erythro-diisotactic, and disyndiotactic. Isotactic polymers have the substituents on the same side of the polymer chain. Syndiotactic polymers have the substituents alternating sides. Diisotactic polymers have both substituents on the same side of adjacent monomers. Disyndiotactic polymers have the substituents alternating between threo and erythro arrangements on adjacent monomers. Newman projections are used to illustrate these different arrangements.

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    This document discusses the tacticity of polymers made from 1,2-disubstituted vinyl monomers. It defines three possible stereoregular patterns for these polymers: threo-diisotactic, erythro-diisotactic, and disyndiotactic. Isotactic polymers have the substituents on the same side of the polymer chain. Syndiotactic polymers have the substituents alternating sides. Diisotactic polymers have both substituents on the same side of adjacent monomers. Disyndiotactic polymers have the substituents alternating between threo and erythro arrangements on adjacent monomers. Newman projections are used to illustrate these different arrangements.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    375 views4 pages

    Tacticity

    Uploaded by

    chemasim
    This document discusses the tacticity of polymers made from 1,2-disubstituted vinyl monomers. It defines three possible stereoregular patterns for these polymers: threo-diisotactic, erythro-diisotactic, and disyndiotactic. Isotactic polymers have the substituents on the same side of the polymer chain. Syndiotactic polymers have the substituents alternating sides. Diisotactic polymers have both substituents on the same side of adjacent monomers. Disyndiotactic polymers have the substituents alternating between threo and erythro arrangements on adjacent monomers. Newman projections are used to illustrate these different arrangements.

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    © All Rights Reserved
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    Download as pdf or txt
    of 4
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    The passage discusses the different types of tacticity (isotactic, syndiotactic, diisotactic) that can occur in vinyl polymers based on the stereochemistry of substituents on adjacent monomers.

    There are three possible stereoregular patterns when two different substituents are present on the monomers: threo-diisotactic, erythro-diisotactic, and disyndiotactic.

    Threo and erythro refer to the relative positions of the two different substituents on adjacent carbons in the polymer chain based on their Newman projections - threo has them on the same side while erythro has them on opposite sides.

    Chem 181/281 RLG v. W02 p.

    1 of 4
    Chem 181/281 Tacticity of Polymers from 1,2-disubstituted vinyl monomers


    H H H H
    R
    R R R
    R
    R R
    R
    H
    H
    H H H
    H H H H
    H
    H H H
    R
    R R
    R
    R
    R
    R R R
    H
    H
    R
    R
    R
    POLYMERS MADE FROM RCH=CHR MONOMERS
    isotactic
    If we examine the configuration of the carbon atoms circled in green and pink, looking toward the right:
    If we again examine the configuration of the carbon atoms circled in green and pink, looking toward the
    polymer chain (up and away)
    polymer chain
    (down and away)
    polymer chain (up and away)
    In both cases, the clockwise sequence is H-R-polymer. That is, the configuration of adjacent carbon
    atoms is the same. So this structure is called isotactic.
    R
    H
    H
    2.
    syndiotactic
    1.
    Chem 181/281 Tacticity of Vinyl Polymers, p. 2 of 4)

    R H
    H R'
    H R
    H
    R'
    H R
    POLYMERS MADE FROM R'CH=CHR MONOMERS
    polymer chain
    If the two substituents are not the same (RR'), there are three possible stereoregular patterns: threo-
    diisotactic, erythro-diisotactic, and disyndiotactic. Now we revert to the conventional use of "isotactic"
    and "syndiotactic" that are used for mono-substituted vinyl polymers.
    polymer
    chain
    polymer
    chain
    When the R groups on adjacent monomer unitsare all on the same side, and the R' groups are also
    all on the same side, we have a diisotactic structure. In order to see how the threo and erythro
    designations arise, we must first look at how those terms are defined. The following diagrams show
    the (eclipsed) Fisher projections and the corresponding Newman projections, first eclipsed ( cis backbone),
    then rotated as it would be if the polymer had an all transbackbone conformation.
    THREO
    H R'
    H
    R
    polymer
    chain
    polymer chain
    R' H
    polymer
    chain
    R
    H R
    H R
    H
    R
    polymer
    chain

    H
    R' H
    R'
    H
    polymer chain H
    polymer chain
    R'
    R' H
    polymer
    chain
    polymer
    chain
    ERYTHRO
    polymer
    chain
    Fisher projection
    Newman projection
    Chem 181/281 Tacticity of Vinyl Polymers, p. 3 of 4)
    H H H H
    H
    H H H
    H
    R
    R R
    R
    R'
    R'
    R' R' R'
    H R H
    R
    threo
    polymer
    chain
    Newman projections showing the threo
    If we now examine the diisotactic structure below, and draw the Newman projection for the two
    carbon atoms circled with the green (left) ellipse, we see that the Newman projection at left
    matches the threo arrangement, in that R and R' are on the same side. If we chose the carbons
    circled with the pink ellipse, we get the Newman projection shown at the right. Again, both R and
    R' are on the same side.
    polymer
    chain
    3a.
    diisotactic
    H
    R'
    H R'
    polymer
    chain
    polymer
    chain
    H H H H
    R'
    R' R' R'
    R
    R R
    R
    H
    H
    H H H
    Now examine the diisotactic structure below, and draw the Newman projection for the two
    carbon atoms circled with the green (left) ellipse. We see that the Newman projection at left
    matches the erythroarrangement, in that R and R' are on opposite sides (anti-periplanar). If we
    chose the carbons circled with the pink ellipse, we get the Newman projection shown at the right.
    Again, both R and R' are on opposite sides (anti).
    erythro
    arrangment.
    arrangement.
    R'
    3b.
    H
    R
    diisotactic
    polymer
    chain
    polymer
    chain
    Newman projections showing the erythro
    H R
    arrangment.
    arrangement.
    Chem 181/281 Tacticity of Vinyl Polymers, p. 4 of 4)
    H R H R
    H
    R' H R'
    R
    H R
    H
    H
    R'
    H R' H
    H R'
    R
    H
    disyndiotactic
    polymer
    chain
    polymer
    chain
    Newman projections showing alternating thre
    and erythro arrangements.
    R
    R'
    The disyndiotactic structure is shown below. Notice that the R groups are on alternating sides in
    adjacent monomer units, and the R' groups alternate as well. Hence the name disyndiotactic.
    TheNewman projections that result from selecting the carbons in each of the two ellipses are
    shown below.
    polymer
    chain
    polymer
    H
    H
    4.
    Notice that the configurations at adjacent carbons alternate (threo, erythro). By simply
    moving our ellipse one carbon to the right, we observe the opposite stereochemistry. We could not
    distinguish between erythro and threo unless the polymer chain ends were distinguishable. Generally,
    for long polymer chains, we treat the "ends" (the 'polymer chain' label in our Newman projections)
    as identical. If this is so, then we can only describe one stereoregular disyndiotactic arrangement
    that arises from R'CH=CHR monomers. The erythro and threo designations have no meaning.
    chain

    R'
    o

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