Odd–even alternations in helical propensity of a homologous series of hydrocarbons

Johan A. Pradeilles, Siying Zhong, Márton Baglyas, György Tarczay, Craig P. Butts, Eddie L. Myers, Varinder K. Aggarwal

Research output: Contribution to journalArticle (Academic Journal)

Abstract

Odd and even homologues of some n-alkane-based systems are known to exhibit notably different trends in solid-state properties; a well-known illustration is the zigzag plot of their melting point versus chain length. Odd–even effects in the solid state often arise from intermolecular interactions that involve fully extended molecules. These effects have also been observed in less condensed phases, such as self-assembled monolayers; however, the origins of these effects in such systems can be difficult to determine. Here we combined NMR and computational analysis to show that all-syn contiguously methyl-substituted hydrocarbons, with chain lengths from C6 to C11, exhibit a dramatic odd–even effect in helical propensity. The even- and odd-numbered hydrocarbons populate regular and less-controlled helical conformations, respectively. This knowledge will guide the design of helical hydrocarbons as rigid scaffolds or as hydrophobic components in soft materials.
Original languageEnglish
Number of pages7
JournalNature Chemistry
DOIs
Publication statusPublished - 2 Mar 2020

Structured keywords

  • BCS and TECS CDTs

Keywords

  • materials chemistry
  • organic chemistry
  • supramolecular chemistry

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