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Secondary structure elements in polylactic acid models

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Abstract

Geometry optimization results are reported on putative elements of secondary structure in decameric units of polylactic acid (PLA) analogous to those seen in protein structure—helical structures (α, π, 310) as well as a β-sheet—employing molecular mechanics, semiempirical, ab initio and density functional methods. The four possible structures of the deca-PLA are generally predicted, with all methods to be within ~15 kcal/mol of each other, with the more stable conformation varying depending on the method employed. The highest-level method employed here (M062x/6-311+G**) predicts that the α, π and 310 structures have very similar energies, with π slightly favored by values within the error limits of the method; this is in contrast with results obtained with less accurate semiempirical and empirical methods, which predict larger differences and other structures as favorites. Relative energies of poly-l and poly-d,l lactic acid structures indicate the former to be energetically-favored over the latter. Three types of weak interactions appear to dictate the relative stabilities of secondary structure elements in polylactic acid structures.

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Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, Babes-Bolyai University, 11 Arany Janos str, Cluj-Napoca, 400028, Romania

    Izabella Irsai, Cornelia Majdik, Alexandru Lupan & Radu Silaghi-Dumitrescu

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  1. Izabella Irsai
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  2. Cornelia Majdik
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  3. Alexandru Lupan
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  4. Radu Silaghi-Dumitrescu
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Correspondence to Radu Silaghi-Dumitrescu.

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Irsai, I., Majdik, C., Lupan, A. et al. Secondary structure elements in polylactic acid models. J Math Chem 50, 703–733 (2012). https://doi.org/10.1007/s10910-011-9919-z

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  • DOI: https://doi.org/10.1007/s10910-011-9919-z

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