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Charge‐transfer complexes between some S‐methylated derivatives of 5,5‐dimethyl‐2,4‐dithiohydantoin and molecular diiodine. A UV‐Visible, IR, FT‐Raman, and 13C NMR study

Charge‐transfer complexes between some S‐methylated derivatives of... Equilibrium constants (K) and thermodynamic parameters for the charge‐transfer complexes between diiodine and Δ3‐4‐S‐methyl‐5,5‐dimethylimidazolidine‐2‐thione (1), 2‐S‐methyl‐5,5‐dimethylimidazolidine‐4‐thione (2), and Δ1‐Δ3‐2S‐methyl‐4‐S‐methyl‐5,5‐dimethylimidazolidine (3) have been determined in CH2Cl2 by UV‐Visible spectroscopy. Depending on the solvent polarity, compound 2 exists as a Δ1 or Δ2 tautomer; both the tautomers are present in CH2Cl2. Compounds 1 and 2 act as good donors (K = 11,000 ± 800 and 640 ± 21 dm3 mol−1, 25°C, respectively) owing to the presence of a thioamidic group in the molecule, whereas in compound 3, the N‐coordination causes a strong reduction of the formation constant (K = 14.6 ± 0.8 dm3 mol−1, 25°C). The high difference between the stability constants of 1 and 2 has been ascribed to an intramolecular hydrogen bonding between NH and the bonded iodine, which can be possible only for 1. Additional spectroscopic data (FT‐Raman, NMR) enables a deeper understanding of the mutual interaction between donors and diiodine. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

Charge‐transfer complexes between some S‐methylated derivatives of 5,5‐dimethyl‐2,4‐dithiohydantoin and molecular diiodine. A UV‐Visible, IR, FT‐Raman, and 13C NMR study

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References (26)

Publisher
Wiley
Copyright
Copyright © 1994 Wiley Subscription Services
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/hc.520050502
Publisher site
See Article on Publisher Site

Abstract

Equilibrium constants (K) and thermodynamic parameters for the charge‐transfer complexes between diiodine and Δ3‐4‐S‐methyl‐5,5‐dimethylimidazolidine‐2‐thione (1), 2‐S‐methyl‐5,5‐dimethylimidazolidine‐4‐thione (2), and Δ1‐Δ3‐2S‐methyl‐4‐S‐methyl‐5,5‐dimethylimidazolidine (3) have been determined in CH2Cl2 by UV‐Visible spectroscopy. Depending on the solvent polarity, compound 2 exists as a Δ1 or Δ2 tautomer; both the tautomers are present in CH2Cl2. Compounds 1 and 2 act as good donors (K = 11,000 ± 800 and 640 ± 21 dm3 mol−1, 25°C, respectively) owing to the presence of a thioamidic group in the molecule, whereas in compound 3, the N‐coordination causes a strong reduction of the formation constant (K = 14.6 ± 0.8 dm3 mol−1, 25°C). The high difference between the stability constants of 1 and 2 has been ascribed to an intramolecular hydrogen bonding between NH and the bonded iodine, which can be possible only for 1. Additional spectroscopic data (FT‐Raman, NMR) enables a deeper understanding of the mutual interaction between donors and diiodine.

Journal

Heteroatom ChemistryWiley

Published: Jan 1, 1994

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