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Hydrogen bonding abilities and self‐association of thiazolidin‐and imidazolidin‐2‐ones and 2‐selenones
Author(s) -
Centric Emilie,
Lauransan Jacques,
Roussel Christian,
Devillanova Francesco A.,
Verani Gaetano
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160553
Subject(s) - chemistry , substituent , hydrogen bond , ring (chemistry) , thiazolidine , proton , medicinal chemistry , carbon tetrachloride , hydrogen , spectroscopy , stereochemistry , molecule , organic chemistry , quantum mechanics , physics
The hydrogen bonding abilities of iV‐methylimidazolidin‐2‐one and ‐2‐selone and thiazolidin‐2‐one and ‐2‐selenone have been studied by ir spectroscopy at 25° in carbon tetrachloride solutions, using dimethyl sulphoxide and 4‐chlorophenol as proton acceptor (K A ) and proton donor (K B ), respectively. The results are compared with those previously reported for N ‐methylimidazolidine‐2‐thione and thiazolidine‐2‐thione. The K A values increase in each series in the order O < S < Se and Kg in the reverse order. The and K B values are discussed in terms of the substituent in ring. The self‐association constants (K D ) are dependent on both K A and K B , although K A seems to be much more important.