Chemically Fueled Transient Geometry Changes in Diphenic Acids

Jayalath, Isuru M.; Wang, Hehe; Mantel, Georgia; Kariyawasam, Lasith S.; Hartley, C. Scott

doi:10.1021/acs.orglett.0c02757

Chemically Fueled Transient Geometry Changes in Diphenic Acids

Journal Article · Tue Sep 22 04:00:00 EDT 2020 · Organic Letters

DOI:https://doi.org/10.1021/acs.orglett.0c02757· OSTI ID:1734533

Jayalath, Isuru M. ^[1]; Wang, Hehe ^[2]; Mantel, Georgia ^[2]; ^[2]; ^[2]

Miami Univ., Oxford, OH (United States); Miami University
Miami Univ., Oxford, OH (United States)

Transient changes in molecular geometry are key to the function of many important biochemical systems. Here, we show that diphenic acids undergo out-of-equilibrium changes in dihedral angle when reacted with a carbodiimide chemical fuel. Treatment of appropriately functionalized diphenic acids with EDC (N-(3-(dimethylamino)propyl)-N'-ethylcarbodiimide hydrochloride) yields the corresponding diphenic anhydrides, reducing the torsional angle about the biaryl bond by ~45°, regardless of substitution. In the absence of steric resistance, the reaction is well-described by a simple mechanism; the resulting kinetic parameters can be used to derive important properties of the system, such as yields and lifetimes. In conclusion, the reaction tolerates steric hindrance ortho to the biaryl bond, although the competing formation of (transient) byproducts complicates quantitative analysis.

View Accepted Manuscript (DOE)

Research Organization:: Miami Univ., Oxford, OH (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0018645

OSTI ID:: 1734533

Journal Information:: Organic Letters, Journal Name: Organic Letters Journal Issue: 19 Vol. 22; ISSN 1523-7060

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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Chemically Fueled Transient Geometry Changes in Diphenic Acids

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