Substituent Effects on Transient, Carbodiimide-Induced Geometry Changes in Diphenic Acids

Jayalath, Isuru M.; Gerken, Madelyn M.; Mantel, Georgia; Hartley, C. Scott

doi:10.1021/acs.joc.1c01385

Title: Substituent Effects on Transient, Carbodiimide-Induced Geometry Changes in Diphenic Acids

Journal Article · 19 August 2021 · Journal of Organic Chemistry

DOI: https://doi.org/10.1021/acs.joc.1c01385 · OSTI ID:1821908

Jayalath, Isuru M. ^[1]; Gerken, Madelyn M. ^[2]; Mantel, Georgia ^[2];

^[2]

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

Nucleotide-induced conformational changes in motor proteins are key to many important cell functions. Inspired by this biological behavior, we report a simple chemically fueled system that exhibits carbodiimide-induced geometry changes. Bridging via transient anhydride formation leads to a significant reduction of the twist about the biaryl bond of substituted diphenic acids, giving a simple molecular clamp. The kinetics are well-described by a simple mechanism, allowing structure–property effects to be determined. The kinetic parameters can be used to derive important characteristics of the system such as the efficiencies (anhydride yields), maximum anhydride concentrations, and overall lifetimes. Transient diphenic anhydrides tolerate steric hindrance ortho to the biaryl bond but are significantly affected by electronic effects, with electron-deficient substituents giving lower yields, peak conversions, and lifetimes. Furthermore, the results provide useful guidelines for the design of functional systems incorporating diphenic acid units.

View Accepted Manuscript (DOE)

Cite

Export

Save

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:: 1821908

Journal Information:: Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 17 Vol. 86; ISSN 0022-3263

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (39)

Chemically Fueled Dissipative Self-Assembly that Exploits Cooperative Catalysis Bal, Subhajit; Das, Krishnendu; Ahmed, Sahnawaz Angewandte Chemie International Edition, Vol. 58, Issue 1 https://doi.org/10.1002/anie.201811749	journal	December 2018
Dissipative Assembly of Macrocycles Comprising Multiple Transient Bonds Hossain, Mohammad Mosharraf; Atkinson, Joshua L.; Hartley, C. Scott Angewandte Chemie International Edition, Vol. 59, Issue 33 https://doi.org/10.1002/anie.202001523	journal	June 2020
Non‐Equilibrium Polymerization of Cross‐β Amyloid Peptides for Temporal Control of Electronic Properties Bal, Subhajit; Ghosh, Chandranath; Ghosh, Tapan Angewandte Chemie International Edition, Vol. 59, Issue 32 https://doi.org/10.1002/anie.202003721	journal	May 2020
Chemically Fueled Volume Phase Transition of Polyacid Microgels Heckel, Jonas; Loescher, Sebastian; Mathers, Robert T. Angewandte Chemie International Edition, Vol. 60, Issue 13 https://doi.org/10.1002/anie.202014417	journal	February 2021
The Transient Covalent Bond in Abiotic Nonequilibrium Systems Kariyawasam, Lasith S.; Hossain, Mohammad Mosharraf; Hartley, C. Scott Angewandte Chemie International Edition, Vol. 60, Issue 23 https://doi.org/10.1002/anie.202014678	journal	February 2021
Motor Protein Receptors Klopfenstein, Dieter R.; Vale, Ronald D.; Rogers, Stephen L. Cell, Vol. 103, Issue 4 https://doi.org/10.1016/S0092-8674(00)00144-6	journal	November 2000
FitSpace Explorer: An algorithm to evaluate multidimensional parameter space in fitting kinetic data Johnson, Kenneth A.; Simpson, Zachary B.; Blom, Thomas Analytical Biochemistry, Vol. 387, Issue 1 https://doi.org/10.1016/j.ab.2008.12.025	journal	April 2009
Dynamic coupling between the motors of DNA replication: hexameric helicase, DNA polymerase, and primase Patel, Smita S.; Pandey, Manjula; Nandakumar, Divya Current Opinion in Chemical Biology, Vol. 15, Issue 5 https://doi.org/10.1016/j.cbpa.2011.08.003	journal	October 2011
Chemical reaction powered transient polymer hydrogels for controlled formation and free release of pharmaceutical crystals Bai, Shengyu; Niu, Xiaofeng; Wang, Hucheng Chemical Engineering Journal, Vol. 414 https://doi.org/10.1016/j.cej.2021.128877	journal	June 2021
Dissipative Self-Assembly: Fueling with Chemicals versus Light Weißenfels, Maren; Gemen, Julius; Klajn, Rafal Chem, Vol. 7, Issue 1 https://doi.org/10.1016/j.chempr.2020.11.025	journal	January 2021
Modification of silicon oxide surfaces by monolayers of an oligoethylene glycol-terminated perfluoroalkyl silane Meiners, Frank; Ross, Jan Henning; Brand, Izabella Colloids and Surfaces A: Physicochemical and Engineering Aspects, Vol. 449 https://doi.org/10.1016/j.colsurfa.2014.02.015	journal	May 2014
Reaction of an introverted carboxylic acid with carbodiimide Iwasawa, Tetsuo; Wash, Paul; Gibson, Christoph Tetrahedron, Vol. 63, Issue 28 https://doi.org/10.1016/j.tet.2007.03.075	journal	July 2007
Structure–Property Effects in the Generation of Transient Aqueous Benzoic Acid Anhydrides by Carbodiimide Fuels Kariyawasam, Lasith S.; Kron, Julie C.; Jiang, Run The Journal of Organic Chemistry, Vol. 85, Issue 2 https://doi.org/10.1021/acs.joc.9b02746	journal	November 2019
Chemically Fueled Transient Geometry Changes in Diphenic Acids Jayalath, Isuru M.; Wang, Hehe; Mantel, Georgia Organic Letters, Vol. 22, Issue 19 https://doi.org/10.1021/acs.orglett.0c02757	journal	September 2020
A survey of Hammett substituent constants and resonance and field parameters Hansch, Corwin.; Leo, A.; Taft, R. W. Chemical Reviews, Vol. 91, Issue 2 https://doi.org/10.1021/cr00002a004	journal	March 1991
Carbodiimide chemistry: recent advances Williams, Andrew; Ibrahim, Ibrahim T. Chemical Reviews, Vol. 81, Issue 6 https://doi.org/10.1021/cr00046a004	journal	December 1981
Reaction of the water-soluble reagent N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide with nucleophiles: participation of the tautomeric cyclic ammonioamidine as a kinetically important intermediate Ibrahim, Ibrahim T.; Williams, Andrew Journal of the American Chemical Society, Vol. 100, Issue 23 https://doi.org/10.1021/ja00491a053	journal	November 1978
Acetylpyridinium ion intermediate in pyridine-catalyzed hydrolysis and acyl transfer reactions of acetic anhydride. Observation, kinetics, structure-reactivity correlations, and effects of concentrated salt solutions Fersht, Alan R.; Jencks, William P. Journal of the American Chemical Society, Vol. 92, Issue 18 https://doi.org/10.1021/ja00721a023	journal	September 1970
Reactions of Carbodiimides. I. The Mechanisms of the Reactions of Acetic Acid with Dicyclohexylcarbodiimide ^1,2 DeTar, DeLos F.; Silverstein, Richard Journal of the American Chemical Society, Vol. 88, Issue 5 https://doi.org/10.1021/ja00957a027	journal	March 1966
The Hydrolysis of Substituted Benzoic Anhydrides ¹ Berliner, Ernst; Altschul, Lucille Holljes Journal of the American Chemical Society, Vol. 74, Issue 16 https://doi.org/10.1021/ja01136a045	journal	August 1952
Regulating Chemically Fueled Peptide Assemblies by Molecular Design Dai, Kun; Fores, Jennifer Rodon; Wanzke, Caren Journal of the American Chemical Society, Vol. 142, Issue 33 https://doi.org/10.1021/jacs.0c04203	journal	July 2020
Molecular Design of Chemically Fueled Peptide–Polyelectrolyte Coacervate-Based Assemblies Späth, Fabian; Donau, Carsten; Bergmann, Alexander M. Journal of the American Chemical Society, Vol. 143, Issue 12 https://doi.org/10.1021/jacs.1c01148	journal	March 2021
A Doubly Kinetically-Gated Information Ratchet Autonomously Driven by Carbodiimide Hydration Borsley, Stefan; Leigh, David A.; Roberts, Benjamin M. W. Journal of the American Chemical Society, Vol. 143, Issue 11 https://doi.org/10.1021/jacs.1c01172	journal	March 2021
Dissipative Assembly of Aqueous Carboxylic Acid Anhydrides Fueled by Carbodiimides Kariyawasam, Lasith S.; Hartley, C. Scott Journal of the American Chemical Society, Vol. 139, Issue 34 https://doi.org/10.1021/jacs.7b06099	journal	August 2017
Uracil-DNA glycosylase acts by substrate autocatalysis Dinner, Aaron R.; Blackburn, G. Michael; Karplus, Martin Nature, Vol. 413, Issue 6857 https://doi.org/10.1038/35099587	journal	October 2001
Structure of a bacterial multidrug ABC transporter Dawson, Roger J. P.; Locher, Kaspar P. Nature, Vol. 443, Issue 7108 https://doi.org/10.1038/nature05155	journal	August 2006
Self-healing microtubules Mulder, Bela M.; Janson, Marcel E. Nature Materials, Vol. 14, Issue 11 https://doi.org/10.1038/nmat4460	journal	October 2015
Supramolecular systems chemistry Mattia, Elio; Otto, Sijbren Nature Nanotechnology, Vol. 10, Issue 2 https://doi.org/10.1038/nnano.2014.337	journal	February 2015
Self-selection of dissipative assemblies driven by primitive chemical reaction networks Tena-Solsona, Marta; Wanzke, Caren; Riess, Benedikt Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-04488-y	journal	May 2018
Stochastic pumping of non-equilibrium steady-states: how molecules adapt to a fluctuating environment Astumian, R. D. Chemical Communications, Vol. 54, Issue 5 https://doi.org/10.1039/C7CC06683J	journal	January 2018
Systems chemistry Ashkenasy, Gonen; Hermans, Thomas M.; Otto, Sijbren Chemical Society Reviews, Vol. 46, Issue 9 https://doi.org/10.1039/C7CS00117G	journal	January 2017
Non-equilibrium supramolecular polymerization Sorrenti, Alessandro; Leira-Iglesias, Jorge; Markvoort, Albert J. Chemical Society Reviews, Vol. 46, Issue 18 https://doi.org/10.1039/C7CS00121E	journal	January 2017
Dissipative out-of-equilibrium assembly of man-made supramolecular materials van Rossum, Susan A. P.; Tena-Solsona, Marta; van Esch, Jan H. Chemical Society Reviews, Vol. 46, Issue 18 https://doi.org/10.1039/C7CS00246G	journal	January 2017
Chemically fueled covalent crosslinking of polymer materials Zhang, Borui; Jayalath, Isuru M.; Ke, Jun Chemical Communications, Vol. 55, Issue 14 https://doi.org/10.1039/C8CC09823A	journal	January 2019
859. The hydrolysis of acetic anhydride. Part VII. Catalysis by pyridine and methylpyridines in acetate buffers Butler, A. R.; Gold, V. Journal of the Chemical Society (Resumed) https://doi.org/10.1039/jr9610004362	journal	January 1961
Stochastically pumped adaptation and directional motion of molecular machines Astumian, R. Dean Proceedings of the National Academy of Sciences, Vol. 115, Issue 38 https://doi.org/10.1073/pnas.1714498115	journal	March 2018
The roles of microtubule-based motor proteins in mitosis Goshima, Gohta; Vale, Ronald D. Journal of Cell Biology, Vol. 162, Issue 6 https://doi.org/10.1083/jcb.200303022	journal	September 2003
Adaptation in Living Systems Tu, Yuhai; Rappel, Wouter-Jan Annual Review of Condensed Matter Physics, Vol. 9, Issue 1 https://doi.org/10.1146/annurev-conmatphys-033117-054046	journal	March 2018
The role of microtubules in secretory protein transport Fourriere, Lou; Jimenez, Ana Joaquina; Perez, Franck Journal of Cell Science, Vol. 133, Issue 2 https://doi.org/10.1242/jcs.237016	journal	January 2020

Similar Records

Chemically Fueled Transient Geometry Changes in Diphenic Acids

Journal Article · 2020 · Organic Letters · OSTI ID:1734533

Jayalath, Isuru M.; Wang, Hehe; Mantel, Georgia; +2 more

Transient Covalent Polymers through Carbodiimide‐Driven Assembly

Journal Article · 2024 · Angewandte Chemie (International Edition) · OSTI ID:2382727

Saha, Nirob K.; Salvia, William S.; Konkolewicz, Dominik; +1 more

Photoresponsive polymers for carbodiimide-fueled transient hydrogels

Journal Article · 2025 · Polymer Chemistry · OSTI ID:2519292

Raji, Ibrahim O.; Wilcox, Torin C.; Hartley, C. Scott; +1 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
carbodiimides
dissipative assembly
hydrocarbons
hydrolysis
kinetics
mixtures
molecular machines
nonequilibrium assembly
substituents

Title: Substituent Effects on Transient, Carbodiimide-Induced Geometry Changes in Diphenic Acids

Citation Formats

References (39)

Similar Records

Related Subjects