1997
DOI: 10.1107/s0108270197002813
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trans- andcis-S—C—C—S Conformations in 5-(2,2'-Dithien-5-yl)-2'-deoxyuridine

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Cited by 3 publications
(3 citation statements)
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“…This type of attractive intramolecular interaction between a thiazole or thiazolidine S and an adjacent carbonyl O at four bonds distance has been observed before and can be viewed simplistically as a Coulombic attraction between the positively charged S and the negatively charged O 41b. Similar CO...S stabilizing interactions have been proposed from the crystal structures of analogous 1,3,4-thiadiazoles 41b and 2-thiophenes 1 X-ray crystal structure of 13d (hydrogens omitted for clarity). …”
Section: Resultssupporting
confidence: 64%
“…This type of attractive intramolecular interaction between a thiazole or thiazolidine S and an adjacent carbonyl O at four bonds distance has been observed before and can be viewed simplistically as a Coulombic attraction between the positively charged S and the negatively charged O 41b. Similar CO...S stabilizing interactions have been proposed from the crystal structures of analogous 1,3,4-thiadiazoles 41b and 2-thiophenes 1 X-ray crystal structure of 13d (hydrogens omitted for clarity). …”
Section: Resultssupporting
confidence: 64%
“…The S-C bond lengths, 1.728 (4) and 1.725 (4) Å, are in good agreement with those in the literature, e.g. 1.734 (2) and 1.721 (3) Å (Han & Choi, 2000), 1.727 (1) and 1.729 (2) Å (Elerman & Elmalı, 1998), and 1.723 (2) and 1.735 (3) Å (Wouters et al, 1997). The C1≡N1 bond distance is 1.153 (4) Å, typical of such a triple bond.…”
Section: S1ðc4supporting
confidence: 91%
“…It also has an influence on the electronic distribution all over the molecule, which might modulate biological activity as already described [40]. The higher potency in the 2,5-thiophene class might also indicate that no intramolecular coulombic attraction between the S(thiophene)-O(carbonyl) occurs as already described in thiophene GABA receptor ligands [42] and other thiophenes acting on different targets [43]. All the changes undertaken to modify the central core have been ineffective for the improvement of the potency of the compounds on the human and mouse enzymes (change of the S position in the ring with respect to the two substituents and introduction of an N atom, exchanging the thiophene by a thiazole).…”
Section: Discussionmentioning
confidence: 86%