Hydrocarbons depending on the chain length and head group adopt different conformations within a water-soluble nanocapsule: 1H NMR and molecular dynamics studies

Rajib Choudhury, Arghya Barman, Rajeev Prabhakar, Vaidhyanathan Ramamurthy

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32 Citations (Scopus)

Abstract

In this study we have examined the conformational preference of phenyl-substituted hydrocarbons (alkanes, alkenes, and alkynes) of different chain lengths included within a confined space provided by a molecular capsule made of two host cavitands known by the trivial name "octa acid" (OA). One- and two-dimensional 1H NMR experiments and molecular dynamics (MD) simulations were employed to probe the location and conformation of hydrocarbons within the OA capsule. In general, small hydrocarbons adopted a linear conformation while longer ones preferred a folded conformation. In addition, the extent of folding and the location of the end groups (methyl and phenyl) were dependent on the group (H2C-CH2, HC=CH, and Cî - C) adjacent to the phenyl group. In addition, the rotational mobility of the hydrocarbons within the capsule varied; for example, while phenylated alkanes tumbled freely, phenylated alkenes and alkynes resisted such a motion at room temperature. Combined NMR and MD simulation studies have confirmed that molecules could adopt conformations within confined spaces different from that in solution, opening opportunities to modulate chemical behavior of guest molecules.

Original languageEnglish
Pages (from-to)398-407
Number of pages10
JournalJournal of Physical Chemistry B
Volume117
Issue number1
DOIs
StatePublished - Jan 10 2013

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Nanocapsules
Hydrocarbons
Chain length
Alkynes
Conformations
Molecular dynamics
Alkenes
alkynes
capsules
hydrocarbons
Nuclear magnetic resonance
molecular dynamics
alkenes
Olefins
Capsules
nuclear magnetic resonance
Water
water
acids
Molecules

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Surfaces, Coatings and Films

Cite this

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abstract = "In this study we have examined the conformational preference of phenyl-substituted hydrocarbons (alkanes, alkenes, and alkynes) of different chain lengths included within a confined space provided by a molecular capsule made of two host cavitands known by the trivial name {"}octa acid{"} (OA). One- and two-dimensional 1H NMR experiments and molecular dynamics (MD) simulations were employed to probe the location and conformation of hydrocarbons within the OA capsule. In general, small hydrocarbons adopted a linear conformation while longer ones preferred a folded conformation. In addition, the extent of folding and the location of the end groups (methyl and phenyl) were dependent on the group (H2C-CH2, HC=CH, and C{\^i} - C) adjacent to the phenyl group. In addition, the rotational mobility of the hydrocarbons within the capsule varied; for example, while phenylated alkanes tumbled freely, phenylated alkenes and alkynes resisted such a motion at room temperature. Combined NMR and MD simulation studies have confirmed that molecules could adopt conformations within confined spaces different from that in solution, opening opportunities to modulate chemical behavior of guest molecules.",
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AU - Prabhakar, Rajeev

AU - Ramamurthy, Vaidhyanathan

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