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Title: The Effect of Pressure on Organic Reactions in Fluids-a New Theoretical Perspective

Abstract

Abstract This Review brings a new perspective to the study of chemical reactions in compressed fluid media. We begin by reviewing the substantial insight gained from more than 50 years of experimental studies on organic reactions in solution under pressure. These led to a proper estimation of the critical roles of volume of activation (Δ ≠ V) and reaction volume (ΔV) in understanding pressure effect on rates and equilibria of organic reactions. A recently developed computational method, the XP‐PCM (extreme pressure polarizable continuum model) method, capable of carrying out quantum mechanical calculations of reaction pathways of molecules under pressure, is introduced. A case study of the Diels–Alder cycloaddition of cyclopentadiene with ethylene serves, in pedagogical detail, to describe the methodology. We then apply the XP‐PCM method to a selection of other pericyclic reactions, including the parent Diels–Alder cycloaddition of butadiene with ethylene, electrocyclic ring‐opening of cyclobutene, electrocyclic ring‐closing of Z‐hexatriene, the [1,5]‐H shift in Z‐pentadiene, and the Cope rearrangement. These serve as examples of some of the most common combinations of Δ ≠ V and ΔV. Interesting phenomena such as a shift in a transition state along a reaction coordinate, a switch of rate‐determining step, and the possible turning of amore » transition state into a stable minimum are revealed by the calculations. A reaction volume profile, the change in the volume of the reacting molecules as the reaction proceeds, emerges as being useful.« less

Authors:
 [1]; ORCiD logo [1]; ORCiD logo [2]
+ Show Author Affiliations
  1. Cornell Univ., Ithaca, NY (United States). Dept. of Chemistry and Chemical Biology, Baker Lab.
  2. Univ. of Parma (Italy). Dept. of Chemical Science, Life Science and Environmental Sustainability
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Energy Frontier Research in Extreme Environments (EFree)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1470609
Alternate Identifier(s):
OSTI ID: 1377943
Grant/Contract Number:  
SC0001057
Resource Type:
Accepted Manuscript
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
Journal Name: Angewandte Chemie (International Edition); Journal Volume: 56; Journal Issue: 37; Related Information: EFree partners with Carnegie Institution of Washington (lead); California Institute of Technology; Colorado School of Mines; Cornell University; Lehigh University; Pennsylvania State University; Journal ID: ISSN 1433-7851
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; catalysis (heterogeneous); solar (photovoltaic); phonons; thermoelectric; energy storage (including batteries and capacitors); hydrogen and fuel cells; superconductivity; charge transport; mesostructured materials; materials and chemistry by design; synthesis (novel materials)

Citation Formats

Chen, Bo, Hoffmann, Roald, and Cammi, Roberto. The Effect of Pressure on Organic Reactions in Fluids-a New Theoretical Perspective. United States: N. p., 2017. Web. doi:10.1002/anie.201705427.
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Chen, Bo, Hoffmann, Roald, & Cammi, Roberto. The Effect of Pressure on Organic Reactions in Fluids-a New Theoretical Perspective. United States. https://doi.org/10.1002/anie.201705427
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Chen, Bo, Hoffmann, Roald, and Cammi, Roberto. Mon . "The Effect of Pressure on Organic Reactions in Fluids-a New Theoretical Perspective". United States. https://doi.org/10.1002/anie.201705427. https://www.osti.gov/servlets/purl/1470609.
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@article{osti_1470609,
title = {The Effect of Pressure on Organic Reactions in Fluids-a New Theoretical Perspective},
author = {Chen, Bo and Hoffmann, Roald and Cammi, Roberto},
abstractNote = {Abstract This Review brings a new perspective to the study of chemical reactions in compressed fluid media. We begin by reviewing the substantial insight gained from more than 50 years of experimental studies on organic reactions in solution under pressure. These led to a proper estimation of the critical roles of volume of activation (Δ ≠ V) and reaction volume (ΔV) in understanding pressure effect on rates and equilibria of organic reactions. A recently developed computational method, the XP‐PCM (extreme pressure polarizable continuum model) method, capable of carrying out quantum mechanical calculations of reaction pathways of molecules under pressure, is introduced. A case study of the Diels–Alder cycloaddition of cyclopentadiene with ethylene serves, in pedagogical detail, to describe the methodology. We then apply the XP‐PCM method to a selection of other pericyclic reactions, including the parent Diels–Alder cycloaddition of butadiene with ethylene, electrocyclic ring‐opening of cyclobutene, electrocyclic ring‐closing of Z‐hexatriene, the [1,5]‐H shift in Z‐pentadiene, and the Cope rearrangement. These serve as examples of some of the most common combinations of Δ ≠ V and ΔV. Interesting phenomena such as a shift in a transition state along a reaction coordinate, a switch of rate‐determining step, and the possible turning of a transition state into a stable minimum are revealed by the calculations. A reaction volume profile, the change in the volume of the reacting molecules as the reaction proceeds, emerges as being useful.},
doi = {10.1002/anie.201705427},
journal = {Angewandte Chemie (International Edition)},
number = 37,
volume = 56,
place = {United States},
year = {Mon Jul 24 00:00:00 EDT 2017},
month = {Mon Jul 24 00:00:00 EDT 2017}
}
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    journal, June 2018

    • Qiu, Lili; Peña-Alvarez, Miriam; Baonza, Valentín G.
    • ChemPhysChem, Vol. 19, Issue 15
    • DOI: 10.1002/cphc.201800319

    Simulation Study to Investigate the Effects of Operational Conditions on Methylcyclohexane Dehydrogenation for Hydrogen Production
    journal, January 2020

    • Hamayun, Muhammad Haris; Maafa, Ibrahim M.; Hussain, Murid
    • Energies, Vol. 13, Issue 1
    • DOI: 10.3390/en13010206

    Glycerol and Q-Tubes: Green Catalyst and Technique for Synthesis of Polyfunctionally Substituted Heteroaromatics and Anilines
    journal, May 2019

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