Events The 4th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

10.3390/ecsoc-4-01931

This submission belongs to the session c. Bioorganic Chemistry and Natural Products of the event The 4th International Electronic Conference on Synthetic Organic Chemistry

Published date

11 Sep, 2000

Citation

Michaela Schwarz, Rainer Kneuer, Markus Heubes, Jens Hartung, Dynamic Behaviour of Cyclic Thiohydroxamic Acid Derivatives Barrier to Rotation about N2O Bonds in 4-Substituted N-Isopropoxythiazole-2(3H)-thiones and N-Isopropoxypyridine-2(1H)-thione, in Proceedings of The 4th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2000, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-4-01931

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Dynamic Behaviour of Cyclic Thiohydroxamic Acid Derivatives Barrier to Rotation about N2O Bonds in 4-Substituted N-Isopropoxythiazole-2(3H)-thiones and N-Isopropoxypyridine-2(1H)-thione

Jens Hartung ¹

Markus Heubes ¹

Rainer Kneuer ¹

Michaela Schwarz ¹

1. Institut für Organische Chemie der Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany

Abstract

Activation parameters [DG200, DH2, DS2] for barriers to rotation about N2O bonds in N-isopropoxypyridine-2(1H)-thione (1) and two 4-substituted N-isopropoxythiazole-2(3H)-thiones 2 and 3 were determined by variable-temperature 1H (600 MHz) and 13C (150 MHz) NMR spectroscopy in the temperature range of T = 135-250 K. The barriers to rotation about N2O bonds in cyclic thiohydroxamic acid O-esters 1, 2, and 3 are explained by a superposition of steric and electronic effects.

Keywords

Barrier to rotation

Dynamic NMR

Pyridinethione

Thiazolethione

Nitrogen-Oxygen bond

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