Intramolecular hydrogen bonding and molecular structure of 2,5-dihydroxyterephthalaldehyde and 4,6-dihydroxyisophthalaldehyde: A gas-phase electron diffraction and ab initio molecular orbital study

Konstantin B. Borisenko, Károly Zauer, István Hargittai

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The molecular structure of 2,5-dihydroxyterephthalaldehyde has been determined from a joint electron diffraction/ab initio investigation, and the molecular structure of 4,6-dihydroxyisophthalaldehyde has been obtained from ab initio calculations at the MP2/6-31G* level. There is considerable intramolecular hydrogen bonding in these structures manifested by the O⋯H and O⋯O distances as well as by the structural changes in the rest of the molecule. These changes are consistent with the notion of resonance-assisted hydrogen bonding. The hydrogen bonding is somewhat stronger in 4,6-dihydroxyisophthalaldehyde than in 2,5-dihydroxyterephthalaldehyde, and this difference may be linked to the difference in the mutual positioning of the interacting formyl and hydroxy groups in these molecules.

Original languageEnglish
Pages (from-to)19303-19309
Number of pages7
JournalJournal of physical chemistry
Volume100
Issue number50
DOIs
Publication statusPublished - Dec 12 1996

ASJC Scopus subject areas

  • Engineering(all)
  • Physical and Theoretical Chemistry

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