Cooperative intramolecularly hydrogen-bonded motif in the structure of 2: 2 complex of TBD with 4-nitrocatechol

S. W. Ng, Pance Naumov, S. Chantrapromma, S. S.S. Raj, H. K. Fun, A. R. Ibrahim, G. Wojciechowski, B. Brzezinski

Research output: Contribution to journalArticle

Abstract

In the crystal of the 2:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene with 4-nitrocatechol the proton from 1-hydroxyl group of 4-nitrocatechol moiety is transferred to TBD to form ion-pair; two adjacent ion-pairs are linked across a center of inversion. The structure exhibits a cooperative, intramolecularly hydrogen-bonded motif. The hydrogen bonds are relatively long and, and they display only minor proton polarizability. The structure of the complex is retained in chloroform solution, as shown by FT-IR and 1H NMR measurement; in acetonitrile, the compound partially dissociates. The partial dissociation is implied by the presence of free cations, and also by that of the (O···H···O)- hydrogen bonds formed between two monodeprotonated 4-nitrocatechol molecules.

Original languageEnglish (US)
Pages (from-to)139-145
Number of pages7
JournalJournal of Molecular Structure
Volume569
Issue number1-3
DOIs
StatePublished - Jul 19 2001

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Hydrogen
Protons
Hydrogen bonds
Ions
Chloroform
Hydroxyl Radical
Cations
Nuclear magnetic resonance
Crystals
Molecules
4-nitrocatechol
triazabicyclodecene
acetonitrile

Keywords

  • 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
  • H NMR spectroscopy
  • Cooperative hydrogen bonds
  • Crystal structure
  • FT-IR spectroscopy
  • Intramolecular hydrogen bonds
  • Strong N-base

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Cooperative intramolecularly hydrogen-bonded motif in the structure of 2 : 2 complex of TBD with 4-nitrocatechol. / Ng, S. W.; Naumov, Pance; Chantrapromma, S.; Raj, S. S.S.; Fun, H. K.; Ibrahim, A. R.; Wojciechowski, G.; Brzezinski, B.

In: Journal of Molecular Structure, Vol. 569, No. 1-3, 19.07.2001, p. 139-145.

Research output: Contribution to journalArticle

Ng, SW, Naumov, P, Chantrapromma, S, Raj, SSS, Fun, HK, Ibrahim, AR, Wojciechowski, G & Brzezinski, B 2001, 'Cooperative intramolecularly hydrogen-bonded motif in the structure of 2: 2 complex of TBD with 4-nitrocatechol', Journal of Molecular Structure, vol. 569, no. 1-3, pp. 139-145. https://doi.org/10.1016/S0022-2860(01)00432-X
Ng, S. W. ; Naumov, Pance ; Chantrapromma, S. ; Raj, S. S.S. ; Fun, H. K. ; Ibrahim, A. R. ; Wojciechowski, G. ; Brzezinski, B. / Cooperative intramolecularly hydrogen-bonded motif in the structure of 2 : 2 complex of TBD with 4-nitrocatechol. In: Journal of Molecular Structure. 2001 ; Vol. 569, No. 1-3. pp. 139-145.
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AB - In the crystal of the 2:2 complex of 1,5,7-triazabicyclo[4.4.0]dec-5-ene with 4-nitrocatechol the proton from 1-hydroxyl group of 4-nitrocatechol moiety is transferred to TBD to form ion-pair; two adjacent ion-pairs are linked across a center of inversion. The structure exhibits a cooperative, intramolecularly hydrogen-bonded motif. The hydrogen bonds are relatively long and, and they display only minor proton polarizability. The structure of the complex is retained in chloroform solution, as shown by FT-IR and 1H NMR measurement; in acetonitrile, the compound partially dissociates. The partial dissociation is implied by the presence of free cations, and also by that of the (O···H···O)- hydrogen bonds formed between two monodeprotonated 4-nitrocatechol molecules.

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