Conformational origins of polymorphism in two forms of flufenamic acid

Sean P. Delaney, Tiffany M. Smith, Timothy M. Korter

Research output: Contribution to journalArticle

18 Scopus citations

Abstract

Flufenamic acid is the most polymorphic rich molecular solid currently known. Here, the origins of the two most common polymorphs of flufenamic acid (Form I and Form III) were investigated using terahertz spectroscopy and solid-state density functional theory. Terahertz spectroscopy probes the low-frequency vibrations that are sensitive to both the intermolecular and intramolecular interactions of molecules in the solid-state. This ability makes terahertz spectroscopy a particularly useful tool for characterizing polymorphic systems, where slight changes in packing arrangements distinguish different polymorphs. Solid-state density functional theory provides a means to achieve better understanding of the chemical origins of the low-frequency vibrations, while also revealing the energetic details of the polymorph relative stabilities. The exploration of these flufenamic acid polymorphs revealed that molecular conformation drives the formation of these particular forms, specifically the magnitude and orientation of the molecular dipoles dictate the preferred solid-state packing arrangements.

Original languageEnglish (US)
Pages (from-to)83-89
Number of pages7
JournalJournal of Molecular Structure
Volume1078
DOIs
StatePublished - 2014

Keywords

  • Conformational energy
  • Far-infrared
  • Low-frequency vibrations
  • Molecular binding forces

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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