Composite Correlated Molecular Orbital Theory Calculations of Ring Strain for Use in Predicting Polymerization Reactions

Confer, Matthew P.; Qu, Taoguang; Rupar, Paul A.; Dixon, David A.

doi:10.1002/cphc.202200133

Title: Composite Correlated Molecular Orbital Theory Calculations of Ring Strain for Use in Predicting Polymerization Reactions

Journal Article · Tue Mar 01 00:00:00 UTC 2022 · ChemPhysChem

DOI: https://doi.org/10.1002/cphc.202200133 · OSTI ID:1981400

^[1]; Qu, Taoguang ^[1]; Rupar, Paul A. ^[1];

^[1]

University of Alabama, Tuscaloosa, AL (United States)

Strained ring systems play an important role in synthesis and can be characterized by the ring strain energy (RSE). The RSE of 3, 4, 5, and 6 membered saturated and unsaturated ring systems containing N, O, P, and S heteroatoms and H, F, SiMe₃, and SO₂Me substituents were calculated at the G3(MP2) composite correlated molecular orbital theory level using up to 5 models to predict the RSE. Generally, the RSE decreased as ring size increased with a substantial decrease from 4 to 5 membered rings. Replacement of a ring CH₂ with P or S reduced the RSE, consistent with less angle strain. The RSE for unsaturated systems were generally greater than for saturated systems due to increased angle strain. No general trends were found with respect to substituent effects. In conclusion, the RSE values suggest that 3-pyrroline and 2-pyrroline and their derivatives may be able to support ring opening metathesis polymerization and warrant further study.

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Research Organization:: Oak Ridge Institute for Science and Education (ORISE), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB)

Grant/Contract Number:: SC0014664

OSTI ID:: 1981400

Journal Information:: ChemPhysChem, Journal Name: ChemPhysChem Journal Issue: 9 Vol. 23; ISSN 1439-4235

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

References (44)

G2ab initio calculations on three-membered rings: Role of hydrogen atoms Alcam�, M.; M�, O.; Y��ez, M. Journal of Computational Chemistry, Vol. 19, Issue 9 https://doi.org/10.1002/(SICI)1096-987X(19980715)19:9<1072::AID-JCC8>3.0.CO;2-N	journal	July 1998
Insektentötende Stoffe I. Über Isolierung und Konstitution des wirksamen Teiles des dalmatinischen Insektenpulvers Staudinger, H.; Ruzicka, L. Helvetica Chimica Acta, Vol. 7, Issue 1 https://doi.org/10.1002/hlca.19240070124	journal	January 1924
Molpro: a general-purpose quantum chemistry program package: Molpro Werner, Hans-Joachim; Knowles, Peter J.; Knizia, Gerald Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 2, Issue 2 https://doi.org/10.1002/wcms.82	journal	July 2011
Structure of Free Polyatomic Molecules Kuchitsu, K. Springer Berlin, Heidelberg https://doi.org/10.1007/978-3-642-45748-7	book	January 1998
Influence of the heteroatom on the structure, bonding and ring strain of a series of three-membered rings containing a second, third, fourth and fifth row elements: a theoretical investigation Romero, Angel H. Structural Chemistry, Vol. 29, Issue 6 https://doi.org/10.1007/s11224-018-1139-8	journal	June 2018
Attractive natural products with strained cyclopropane and/or cyclobutane ring systems Fan, Yao-Yue; Gao, Xin-Hua; Yue, Jian-Min Science China Chemistry, Vol. 59, Issue 9 https://doi.org/10.1007/s11426-016-0233-1	journal	August 2016
Molecular force field and structure of hydrogen sulfide: recent microwave results Cook, Robert L.; De Lucia, Frank C.; Helminger, Paul Journal of Molecular Structure, Vol. 28, Issue 2 https://doi.org/10.1016/0022-2860(75)80094-9	journal	October 1975
Strain energy of three-membered rings: a new ultradiagonal definition as applied to silicon- and carbon-containing species Skancke, Anne; Van Vechten, Deborah; Liebman, Joel F. Journal of Molecular Structure, Vol. 376, Issue 1-3 https://doi.org/10.1016/0022-2860(95)09062-2	journal	February 1996
A fifth-order perturbation comparison of electron correlation theories Raghavachari, Krishnan; Trucks, Gary W.; Pople, John A. Chemical Physics Letters, Vol. 157, Issue 6 https://doi.org/10.1016/S0009-2614(89)87395-6	journal	May 1989
Structure of UDP-N-acetylglucosamine enolpyruvyl transferase, an enzyme essential for the synthesis of bacterial peptidoglycan, complexed with substrate UDP-N-acetylglucosamine and the drug fosfomycin Skarzynski, Tadeusz; Mistry, Anil; Wonacott, Alan Structure, Vol. 4, Issue 12 https://doi.org/10.1016/S0969-2126(96)00153-0	journal	December 1996
Functionalization of multiwalled carbon nanotubes with polyamide 6 by anionic ring-opening polymerization Yang, Mei; Gao, Yong; Li, Huaming Carbon, Vol. 45, Issue 12 https://doi.org/10.1016/j.carbon.2007.07.021	journal	October 2007
The enthalpy of formation of the isomeric 2,3- and 2,5-dihydrofuran Freitas, Vera L. S.; Ribeiro da Silva, Maria D. M. C.; Liebman, Joel F. The Journal of Chemical Thermodynamics, Vol. 97 https://doi.org/10.1016/j.jct.2016.01.011	journal	June 2016
Living ring-opening metathesis polymerization Bielawski, Christopher W.; Grubbs, Robert H. Progress in Polymer Science, Vol. 32, Issue 1, p. 1-29 https://doi.org/10.1016/j.progpolymsci.2006.08.006	journal	January 2007
Applications of Sharpless asymmetric epoxidation in total synthesis Heravi, Majid M.; Lashaki, Tahmineh Baie; Poorahmad, Nasim Tetrahedron: Asymmetry, Vol. 26, Issue 8-9 https://doi.org/10.1016/j.tetasy.2015.03.006	journal	April 2015
Polymerization of Ethylene Oxide, Propylene Oxide, and Other Alkylene Oxides: Synthesis, Novel Polymer Architectures, and Bioconjugation Herzberger, Jana; Niederer, Kerstin; Pohlit, Hannah Chemical Reviews, Vol. 116, Issue 4 https://doi.org/10.1021/acs.chemrev.5b00441	journal	December 2015
Radical Ring-Opening Polymerization: Scope, Limitations, and Application to (Bio)Degradable Materials Tardy, Antoine; Nicolas, Julien; Gigmes, Didier Chemical Reviews, Vol. 117, Issue 3 https://doi.org/10.1021/acs.chemrev.6b00319	journal	January 2017
Accurate Ring Strain Energy Calculations on Saturated Three-Membered Heterocycles with One Group 13–16 Element Planells, Alicia Rey; Ferao, Arturo Espinosa Inorganic Chemistry, Vol. 59, Issue 16 https://doi.org/10.1021/acs.inorgchem.0c01316	journal	July 2020
Emerging and Re-Emerging Warheads for Targeted Covalent Inhibitors: Applications in Medicinal Chemistry and Chemical Biology Gehringer, Matthias; Laufer, Stefan A. Journal of Medicinal Chemistry, Vol. 62, Issue 12 https://doi.org/10.1021/acs.jmedchem.8b01153	journal	December 2018
Variable Temperature ROMP: Leveraging Low Ring Strain Thermodynamics To Achieve Well-Defined Polypentenamers Neary, William J.; Kennemur, Justin G. Macromolecules, Vol. 50, Issue 13 https://doi.org/10.1021/acs.macromol.7b01148	journal	June 2017
Synthesis of Stereoregular Polymers through Ring-Opening Metathesis Polymerization Schrock, Richard R. Accounts of Chemical Research, Vol. 47, Issue 8 https://doi.org/10.1021/ar500139s	journal	June 2014
The Chemistry of Transition Metals with Three-Membered Ring Heterocycles Huang, Chung-Yang (Dennis); Doyle, Abigail G. Chemical Reviews, Vol. 114, Issue 16 https://doi.org/10.1021/cr500036t	journal	May 2014
Recent Advances in the Metal-Catalyzed Ring Expansions of Three- and Four-Membered Rings Mack, Daniel J.; Njardarson, Jon T. ACS Catalysis, Vol. 3, Issue 2 https://doi.org/10.1021/cs300771d	journal	January 2013
The group equivalent reaction: An improved method for determining ring strain energy Bachrach, Steven M. Journal of Chemical Education, Vol. 67, Issue 11 https://doi.org/10.1021/ed067p907	journal	November 1990
A Hierarchy of Homodesmotic Reactions for Thermochemistry Wheeler, Steven E.; Houk, Kendall N.; Schleyer, Paul v. R. Journal of the American Chemical Society, Vol. 131, Issue 7 https://doi.org/10.1021/ja805843n	journal	February 2009
Ring Strain Energies from ab Initio Calculations Dudev, Todor; Lim, Carmay Journal of the American Chemical Society, Vol. 120, Issue 18 https://doi.org/10.1021/ja973895x	journal	May 1998
Enol Ethers Are Effective Monomers for Ring-Opening Metathesis Polymerization: Synthesis of Degradable and Depolymerizable Poly(2,3-dihydrofuran) Feist, John D.; Xia, Yan Journal of the American Chemical Society, Vol. 142, Issue 3 https://doi.org/10.1021/jacs.9b11834	journal	December 2019
Cationic Ring-Opening Polymerization of Oxetane via a Non-Steady-State Controlled Polymerization Process: A Comparison of Initiators Yielding Living and Nonliving Polymers Bouchékif, Hassen; Philbin, Marcia I.; Colclough, Eamon Macromolecules, Vol. 41, Issue 6 https://doi.org/10.1021/ma062761d	journal	March 2008
The resurgence of covalent drugs Singh, Juswinder; Petter, Russell C.; Baillie, Thomas A. Nature Reviews Drug Discovery, Vol. 10, Issue 4 https://doi.org/10.1038/nrd3410	journal	April 2011
The anionic ring-opening polymerization of N -(methanesulfonyl)azetidine Reisman, Louis; Rowe, Elizabeth A.; Liang, Qiaoli Polymer Chemistry, Vol. 9, Issue 13 https://doi.org/10.1039/C8PY00074C	journal	January 2018
Aziridines and azetidines: building blocks for polyamines by anionic and cationic ring-opening polymerization Gleede, Tassilo; Reisman, Louis; Rieger, Elisabeth Polymer Chemistry, Vol. 10, Issue 24 https://doi.org/10.1039/C9PY00278B	journal	January 2019
Recent advances in the total synthesis of cyclobutane-containing natural products Li, Jinshan; Gao, Kai; Bian, Ming Organic Chemistry Frontiers, Vol. 7, Issue 1 https://doi.org/10.1039/C9QO01178A	journal	January 2020
Synthesis of polycaprolactone: a review Labet, Marianne; Thielemans, Wim Chemical Society Reviews, Vol. 38, Issue 12 https://doi.org/10.1039/b820162p	journal	January 2009
Recent advances in the total synthesis of cyclopropane-containing natural products Chen, David Y. -K.; Pouwer, Rebecca H.; Richard, Jean-Alexandre Chemical Society Reviews, Vol. 41, Issue 13 https://doi.org/10.1039/c2cs35067j	journal	January 2012
Gaussian basis sets for use in correlated molecular calculations. X. The atoms aluminum through argon revisited Dunning, Thom H.; Peterson, Kirk A.; Wilson, Angela K. The Journal of Chemical Physics, Vol. 114, Issue 21 https://doi.org/10.1063/1.1367373	journal	June 2001
A full coupled‐cluster singles and doubles model: The inclusion of disconnected triples Purvis, George D.; Bartlett, Rodney J. The Journal of Chemical Physics, Vol. 76, Issue 4 https://doi.org/10.1063/1.443164	journal	February 1982
Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen Dunning, Thom H. The Journal of Chemical Physics, Vol. 90, Issue 2 https://doi.org/10.1063/1.456153	journal	January 1989
Electron affinities of the first‐row atoms revisited. Systematic basis sets and wave functions Kendall, Rick A.; Dunning, Thom H.; Harrison, Robert J. The Journal of Chemical Physics, Vol. 96, Issue 9 https://doi.org/10.1063/1.462569	journal	May 1992
Coupled‐cluster methods with noniterative triple excitations for restricted open‐shell Hartree–Fock and other general single determinant reference functions. Energies and analytical gradients Watts, John D.; Gauss, Jürgen; Bartlett, Rodney J. The Journal of Chemical Physics, Vol. 98, Issue 11 https://doi.org/10.1063/1.464480	journal	June 1993
Density‐functional thermochemistry. III. The role of exact exchange Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652 https://doi.org/10.1063/1.464913	journal	April 1993
Gaussian-3 theory using reduced Mo/ller-Plesset order Curtiss, Larry A.; Redfern, Paul C.; Raghavachari, Krishnan The Journal of Chemical Physics, Vol. 110, Issue 10 https://doi.org/10.1063/1.478385	journal	March 1999
The Molpro quantum chemistry package Werner, Hans-Joachim; Knowles, Peter J.; Manby, Frederick R. The Journal of Chemical Physics, Vol. 152, Issue 14 https://doi.org/10.1063/5.0005081	journal	April 2020
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
Coupled-cluster theory in quantum chemistry Bartlett, Rodney J.; Musiał, Monika Reviews of Modern Physics, Vol. 79, Issue 1 https://doi.org/10.1103/RevModPhys.79.291	journal	February 2007
Optimization of Gaussian-type basis sets for local spin density functional calculations. Part I. Boron through neon, optimization technique and validation Godbout, Nathalie; Salahub, Dennis R.; Andzelm, Jan Canadian Journal of Chemistry, Vol. 70, Issue 2 https://doi.org/10.1139/v92-079	journal	February 1992

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Chemistry
Physics
correlated G3 (MP2) molecular orbital theory
heterocycle
polymer
polymerization
ring strain energy
ring-opening

Title: Composite Correlated Molecular Orbital Theory Calculations of Ring Strain for Use in Predicting Polymerization Reactions

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