Directionality and site selectivity of N⋯Cl halogen bonding in two azaaromatic chloride crystals

Yi Min Zhu, Ti Fang Miao, Yang Yi Yang, Dong Yue Zhuang, Kang Cheng Zheng, Wing Tak Wong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

5 Citations (Scopus)


Two azaaromatic chlorides of bis-2,4-[(2-formoyl)phenoxyl]-6-chloro-[1,3,5]triazine (1) and bis-2,4-(4-carbomethoxyphenoxyl)-6-chloro-[1,3,5]triazine (2) have been synthesized and structurally characterized. The crystal structures of 1 and 2 reveal unusually short intermolecular N⋯Cl distance of 3.095(2) and 3.088(3) Å, meaning the formation of strong halogen bonding. The strengths of the intermolecular N⋯Cl halogen bonding and the molecular electrostatic potentials in these crystal structures have been calculated by Density Functional Theory Calculations. The capacities of the N⋯Cl halogen bonding, lone pair⋯π interaction, π-π stack and C-H⋯O hydrogen bonding in the directionality of supramolecular self-assembly have been analyzed by structural study and theoretical calculations. The site selectivity of the N⋯Cl halogen bonding is illustrated by the difference of electrostatic potential of the N atoms on the molecule.
Original languageEnglish
Pages (from-to)274-279
Number of pages6
JournalJournal of Molecular Structure
Issue number1-3
Publication statusPublished - 30 Jun 2010


  • DFT calculations
  • Directionality
  • Halogen bonding
  • Molecular electrostatic potential
  • Site selectivity

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry


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