From competition to commensuration by two major hydrogen-bonding motifs

Sihui Long, Panpan Zhou, Sean Parkin, Tonglei Li

Research output: Contribution to journalArticlepeer-review

20 Scopus citations


Carboxylic acid-acid hydrogen-bonding dimer and acid-pyridine hydrogen-bonding motif are two competing supramolecular synthons that a molecule possessing both carboxylic acid and pyridine functional groups could form in the solid state. Their coexistence has been observed but for the molecules with the molar ratio of carboxylic acid and pyridine groups being greater than 1:1. In this crystal engineering study, 2-[phenyl(propyl)amino]nicotinic acid with a 1:1 molar ratio of these two functional groups was discovered to have two polymorphs, in which one consists of unique hydrogen-bonded tetramer units bearing both acid-acid and acid-pyridine hydrogen-bonding motifs, while the other is composed of acid-pyridine hydrogen-bonded chains. Quantum mechanical calculations were employed to unravel the essence of the coexistence of the two vying counterparts as well as the origins of the tetramer and chain structures.

Original languageEnglish
Pages (from-to)27-31
Number of pages5
JournalCrystal Growth and Design
Issue number1
StatePublished - Jan 2 2014

ASJC Scopus subject areas

  • Chemistry (all)
  • Materials Science (all)
  • Condensed Matter Physics


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