PulseExploreJournal ClubDebatesTrendingResearchersJournals
Instagram
HomeExploreJournal ClubTrending
Synapse
⌘+K
Synapse
February 22, 2026Inorganic Chemistry1 citationsOpen Access

Preparation and Characterization of Oxalyl Dicyanide

View Full Paper
SRSven RingelbandPhilipps University of MarburgTCTheodore CohenPhilipps University of MarburgFTFrank TamborninoPhilipps University of Marburg

Key Points

  • The study aims to synthesize and characterize oxalyl dicyanide and its derivatives.
  • Synthesis of oxalyl dicyanide from oxalyl chloride and trimethylsilyl cyanide.
  • Characterization through crystal structure analysis and vibrational spectroscopy.
  • Use of quantum chemical calculations to support findings.
  • Analysis of the NMR spectrum of the compound.
  • Investigation of hydrolysis products via single-crystal X-ray diffraction.
  • Oxalyl dicyanide exhibits C2h symmetry with a trans-anti configuration.
  • Two distinct resonances observed in the 13C NMR spectrum at 159.8 and 109.9 ppm.
  • Characteristic stretching vibrations identified at 2243 cm-1 (C≡N) and 1734 cm-1 (C═O).
  • Rapid hydrolysis yields oxalic acid and hydrogen cyanide, with transient formation of tetraol.

Abstract

Oxalyl dicyanide and its 1,4-dioxane adduct were obtained as colorless crystalline solids from the reaction of oxalyl chloride with trimethylsilyl cyanide. Their crystal structures and vibrational spectra, supported by quantum chemical calculations, are presented. In the solid state, oxalyl dicyanide adopts C2h symmetry with the preferred trans-anti configuration. The 13C NMR spectrum shows two distinct resonances at 159.8 and 109.9 ppm, while characteristic ν(C≡N) and ν(C═O) stretching vibrations are observed at 2243 and 1734 cm-1, respectively. Hydrolysis proceeds rapidly to oxalic acid and hydrogen cyanide, with transient formation of the unusual tetraol 2,2,3,3-tetrahydroxysuccinonitrile, as confirmed by single-crystal X-ray diffraction.

Ask AI
Helpful
Bookmark
Share
View Full Paper

Cite This Study

Ringelband et al. (2026) studied this question.

synapsesocial.com/papers/699a9d8e482488d673cd3792https://doi.org/10.1021/acs.inorgchem.5c05620
Ask AI
Helpful
Bookmark
Share
View Full Paper

Also Consider

Synapse has enriched 5 closely related papers on similar clinical questions. Consider them for comparative context:

  1. 1The crystal structure of 5,5-dihydroxybarbituric acid trihydrate1965 · 23 citations
  2. 2Generalized Gradient Approximation Made Simple1996 · 216,350 citations
  3. 3X-Ray Analysis of the (1:1) Addition Compounds of 1,4-Dioxan with Oxalyl Chloride resp. Oxalyl Bromide.1965 · 26 citations
  4. 4Crystal structure refinement with SHELXL2014 · 43,543 citations
  5. 5Structure and spectra of the 1:1 addition compound of 1,4-dioxane and oxalyl fluoride1987 · 5 citations