Formation of a ground state twisted-internal-charge-transfer conformer of 4-(dimethylamino)benzaldehyde

G. P. Kushto, P. W. Jagodzinski

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Ultraviolet absorption spectra and visible Raman spectra were collected for 4-(dimethylamino)benzaldehyde (DABA) in aqueous solution in the pH range of 9.56 to -1.08. Equilibrium arguments show that only the free base and the dimethylamino protonated species will be present in appreciable concentrations in this pH range. Protonation leads to increased sp3 hybridization about the amino nitrogen with rotation to form a twisted- internal-charge-transfer (TICT) conformer. Molar absorptivities were calculated for the 352 nm band and these values were used to calculate the angle of rotation of the dimethylamino group out of the ring plane. The Raman spectrum of DABA in concentrated hydrochloric acid solution is consistent with a TICT structure in which the amino group is rotated 90°out of the plane.

Original languageEnglish (US)
Pages (from-to)215-223
Number of pages9
JournalJournal of Molecular Structure
Volume516
Issue number2-3
DOIs
StatePublished - Jan 25 2000
Externally publishedYes

Keywords

  • 4-(Dimethylamino)benzaldehyde
  • Raman spectra
  • Twisted-internal-charge- transfer
  • Ultraviolet spectra

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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