Aspects of structural thiohydroxamate chemistry—on a systematic in the 5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione series
Jens Hartung
1
,
Uwe Bergsträßer
1
,
Kristina Daniel
1
,
Nina Schneiders
1
,
Ingrid Svoboda
2
,
Hartmut Fuess
2
Publication type: Journal Article
Publication date: 2009-03-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Bond angles at thiohydroxamate oxygen in crystal structures of 3-alkoxy-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thiones gradually increased with the size of the 3-alkoxy substituent. This effect was attributed to strain on the basis of (i) a linear free energy relationship (Taft–Dubois correlation) and (ii) signal coalescence from resonances of diastereotopic CH3 groups in solution (O-cumyl substituent; DNMR). Substitution at oxygen along the sequence OR (R=prim-, sec-, and tert-alkyl), OH, and OLi was reflected in a gradual decrease of N,O distances and lengthening of associated C,S bonds. The responsivity for these changes was more pronounced in the thiazole-2(3H)-thione than in the pyridine-2(1H)-thione series.
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Hartung J. et al. Aspects of structural thiohydroxamate chemistry—on a systematic in the 5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione series // Tetrahedron. 2009. Vol. 65. No. 12. pp. 2567-2573.
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Hartung J., Bergsträßer U., Daniel K., Schneiders N., Svoboda I., Fuess H. Aspects of structural thiohydroxamate chemistry—on a systematic in the 5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione series // Tetrahedron. 2009. Vol. 65. No. 12. pp. 2567-2573.
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RIS
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TY - JOUR
DO - 10.1016/j.tet.2009.01.067
UR - https://doi.org/10.1016/j.tet.2009.01.067
TI - Aspects of structural thiohydroxamate chemistry—on a systematic in the 5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione series
T2 - Tetrahedron
AU - Hartung, Jens
AU - Bergsträßer, Uwe
AU - Daniel, Kristina
AU - Schneiders, Nina
AU - Svoboda, Ingrid
AU - Fuess, Hartmut
PY - 2009
DA - 2009/03/01
PB - Elsevier
SP - 2567-2573
IS - 12
VL - 65
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{2009_Hartung,
author = {Jens Hartung and Uwe Bergsträßer and Kristina Daniel and Nina Schneiders and Ingrid Svoboda and Hartmut Fuess},
title = {Aspects of structural thiohydroxamate chemistry—on a systematic in the 5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione series},
journal = {Tetrahedron},
year = {2009},
volume = {65},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016/j.tet.2009.01.067},
number = {12},
pages = {2567--2573},
doi = {10.1016/j.tet.2009.01.067}
}
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MLA
Copy
Hartung, Jens, et al. “Aspects of structural thiohydroxamate chemistry—on a systematic in the 5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione series.” Tetrahedron, vol. 65, no. 12, Mar. 2009, pp. 2567-2573. https://doi.org/10.1016/j.tet.2009.01.067.