Persistent Self-Association of Solute Molecules in Solution

Weiwei Tang, Huaping Mo, Mingtao Zhang, Sean Parkin, Junbo Gong, Jingkang Wang, Tonglei Li

Research output: Contribution to journalArticlepeer-review

30 Scopus citations


The structural evolvement of a solute determines the crystallization outcome. The self-association mechanism leading to nucleation, however, remains poorly understood. Our current study explored the solution chemistry of a model compound, tolfenamic acid (TFA), in three different solvents mainly by solution NMR. It was found that hydrogen-bonded pairs of solute-solute or solute-solvent stack with each through forming a much weaker π-π interaction as the concentration increases. Depending on the solvent, configurations of the solution species may be retained in the resultant crystal structure or undergo rearrangement. Yet, the π-π stacking is always retained in the crystal regardless of the solvent used for the crystallization. The finding suggests that nucleation not only involves the primary intermolecular interaction (hydrogen bonding) but also engages the secondary forces in the self-assembly process.

Original languageEnglish
Pages (from-to)10118-10124
Number of pages7
JournalJournal of Physical Chemistry B
Issue number43
StatePublished - Nov 2 2017

Bibliographical note

Funding Information:
W.T. acknowledges funding support from the China Scholarship Council (CSC) and the National Natural Science Foundation of China (NSFC; Nos. 21676179 and 91634117). The work was also supported by Chao Endowment at Purdue University.

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus subject areas

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


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