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Rigid Single Carbon-Carbon Bond That Does Not Rotate in Water

Rigid Single Carbon-Carbon Bond That Does Not Rotate in Water

Manuel Gadogbe, Yadong Zhou, Shengli Zou, Dongmao Zhang

J Phys Chem B. 2016 Mar 10;120(9):2418-22.

PMID: 26882311

Abstract:

Carbon-carbon bond is one of the most ubiquitous molecular building blocks for natural and man-made materials. Rotational isomerization is fundamentally important for understanding the structure and reactivity of chemical and biological molecules. Reported herein is the first demonstration that a single C-C bond does not rotate in water. The two distal C-S bonds in both 1,2-ethanedithiolate ((-)S-CH2-CH2-S(-), 1,2-EDT(2-)) and 2,3-butanedithiolate (2,3-BuDT(2-)) are exclusively in the trans conformer with reference to their respective center single C-C bond. In contrast, both trans and gauche conformers are observed in neutral 1,2-ethanedithiol (1,2-EDT) and 2, 3-butanedithiol (2,3-BuDT). The insight from this work should be important for understanding the charge effect on the molecular conformation in aqueous solutions.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP4532643	2,3-Butanedithiol		4532-64-3	Price

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