AMHB: (Anti)aromaticity-modulated hydrogen bonding

Tayeb Kakeshpour, Judy I. Wu, James E. Jackson

Research output: Contribution to journalArticle

  • 7 Citations

Abstract

This in silico survey shows that changes in the (anti)aromatic character of π-conjugated heterocycles can be used to fine-tune their hydrogen (H-)bond strengths. Upon H-bonding dimerization, the π-electrons of these rings can be polarized to reinforce or disrupt their (anti)aromatic π-conjugated circuits (πCCs) and stabilize or destabilize the resulting H-bonded complexes. H-bonding interactions that enhance aromaticity or relieve antiaromaticity are fortified, whereas those that intensify antiaromaticity or disrupt aromaticity are weakened, relative to analogues lacking full π-circuits. Computed dissected nucleus-independent chemical shifts, NICS(1)zz, reveal a uniform pattern and document changes in the magnetic (anti)aromatic character of the heterocycles considered. Recognition of this (anti)aromaticity-modulated H-bonding (AMHB) phenomenon offers insights into a range of fields from organocatalysis and self-assembly to pharmaceutical chemistry and molecular biology.

LanguageEnglish (US)
Pages3427-3432
Number of pages6
JournalJournal of the American Chemical Society
Volume138
Issue number10
DOIs
StatePublished - Mar 16 2016

Profile

Pharmaceutical Chemistry
Dimerization
Hydrogen Bonding
Computer Simulation
Molecular Biology
Hydrogen
Hydrogen bonds
Electrons
Molecular biology
Networks (circuits)
Chemical shift
Self assembly
Surveys and Questionnaires

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

AMHB : (Anti)aromaticity-modulated hydrogen bonding. / Kakeshpour, Tayeb; Wu, Judy I.; Jackson, James E.

In: Journal of the American Chemical Society, Vol. 138, No. 10, 16.03.2016, p. 3427-3432.

Research output: Contribution to journalArticle

Kakeshpour, Tayeb ; Wu, Judy I. ; Jackson, James E./ AMHB : (Anti)aromaticity-modulated hydrogen bonding. In: Journal of the American Chemical Society. 2016 ; Vol. 138, No. 10. pp. 3427-3432
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