Preferred formation of the carboxylic acid-pyridine heterosynthon in 2-anilinonicotinic acids

Peng Chen, Zhifei Zhang, Sean Parkin, Panpan Zhou, Kai Cheng, Conggang Li, Faquan Yu, Sihui Long

Research output: Contribution to journalArticlepeer-review

11 Scopus citations


The carboxylic acid-carboxylic acid homosynthon and carboxylic acid-pyridine heterosynthon are two competing supramolecular synthons in 2-anilinonicotinic acids that possess both carboxylic acid and pyridine functionalities. Previously we demonstrated that carboxylic acid-pyridine heterosynthons can be selectively formed in crystals by chemically introducing bulky functional groups to the aniline ring of the molecules. In this study we show that with the same philosophy, but a different strategy, i.e., adding substituent groups to the nitrogen bridging the two aromatic rings, we can also achieve the preferential formation of the carboxylic acid-pyridine heterosynthon over the carboxylic acid-carboxylic acid homosynthon. This is a new case of how molecular conformation can affect intermolecular interactions and consequent crystal packing.

Original languageEnglish
Pages (from-to)81101-81109
Number of pages9
JournalRSC Advances
Issue number84
StatePublished - 2016

Bibliographical note

Funding Information:
PC and SL thank Natural Science Foundation of Hubei Province (2014CFB787) and the Innovation Fund from Wuhan Institute of Technology (CX2014002) for financial support. PPZ thanks the financial support by the National Natural Science Foundation of China (Grant No. 21403097) and the Fundamental Research Funds for the Central Universities (lzujbky-2014-182). The authors also thank Dr Tonglei Li of Purdue University for helpful discussions.

Publisher Copyright:
© The Royal Society of Chemistry 2016.

ASJC Scopus subject areas

  • Chemistry (all)
  • Chemical Engineering (all)


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