Data from: Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis
benzaldehyde_anilinoborane
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Description | Pathway for reaction between benzaldehyde and anilinoborane |
Scope And Content | Contains .log, .chk, and .fchk files for the frequency calculations required for the thermodynamic parameters involving the reaction of benzaldehyde and anilinoborane. Sub folders are used to contain the files for each species along the reaction path including: aldehyde, aminoborane, aminoborane_addition_ts, hemiaminal_int (with further sub folders), imine, intra_hshift_ts, and PinBOH. |
benzaldehyde_c6f5anilinoborane
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Description | Pathway for reaction between benzaldehyde and c6f5anilinoborane |
Scope And Content | Contains .log, .chk, and .fchk files for the frequency calculations required for the thermodynamic parameters involving the reaction of benzaldehyde and c6f5anilinoborane. Sub folders are used to contain the files for each species along the reaction path including: aldehyde, aminoborane, aminoborane_addition_ts, hemiaminal_int (with further sub folders), imine, intra_hshift_ts, and PinBOH. |
benzaldehyde_isopropylaminoborane
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Description | Pathway for reaction between benzaldehyde and isopropylaminoborane |
Scope And Content | Contains .log, .chk, and .fchk files for the frequency calculations required for the thermodynamic parameters involving the reaction of benzaldehyde and isopropylaminoborane. Sub folders are used to contain the files for each species along the reaction path including: aldehyde, aminoborane, aminoborane_addition_ts, hemiaminal_int (with further sub folders), imine, intra_hshift_ts, and PinBOH. |
isobutyraldehyde_anilinoborane
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Description | Pathway for reaction between isobutrylaldehyde and anilinoborane |
Scope And Content | Contains .log, .chk, and .fchk files for the frequency calculations required for the thermodynamic parameters involving the reaction of isobutyraldehyde and anilinoborane. Sub folders are used to contain the files for each species along the reaction path including: aldehyde, aminoborane, aminoborane_addition_ts, hemiaminal_int (with further sub folders), imine, intra_hshift_ts, and PinBOH. |
isobutyraldehyde_c6f5anilinoborane
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Description | Pathway for reaction between isobutrylaldehyde and c6f5anilinoborane |
Scope And Content | Contains .log, .chk, and .fchk files for the frequency calculations required for the thermodynamic parameters involving the reaction of isobutyraldehyde and c6f5anilinoborane. Sub folders are used to contain the files for each species along the reaction path including: aldehyde, aminoborane, aminoborane_addition_ts, hemiaminal_int (with further sub folders), imine, intra_hshift_ts, and PinBOH. |
isobutyraldehyde_isopropylaminoborane
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Description | Pathway for reaction between isobutrylaldehyde and isopropylaminoborane |
Scope And Content | Contains .log, .chk, and .fchk files for the frequency calculations required for the thermodynamic parameters involving the reaction of isobutyraldehyde and isopropylaminoborane. Sub folders are used to contain the files for each species along the reaction path including: aldehyde, aminoborane, aminoborane_addition_ts, hemiaminal_int (with further sub folders), imine, intra_hshift_ts, and PinBOH. |
- Collection
- Cite This Work
-
Junor, Glen P.; Romero, Erik A.; Chen, Xi; Jazzar, Rodolphe; Bertrand, Guy (2019). Data From: Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis. UC San Diego Library Digital Collections. https://doi.org/10.6075/J00Z71HW
- Description
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Abstract: Primary aminoboranes (RNHBR2), which are readily available by spontaneous dehydrocoupling of amines and boranes cleanly react at room temperature with aldehydes to give aldimines. The overall transformation from amines to aldimines can be conveniently performed by a sequential one-pot reaction. This synthetic strategy is especially useful for electron poor and bulky amines which are reluctant to react with aldehydes under dehydration conditions. Using a Glorius robustness screen, we show that this methodology is chemoselective, and functional group tolerant. Computational and experimental data support the irreversible formation of the aldimine product in marked contrast with traditional methods.
- Scope And Content
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Data pertaining to each computed pathway, for the reaction between aldehydes and aminoboranes, can be downloaded. Within each .zip file are a number of folders containing .log, .chk, and .fchk files for each species along the reaction coordinate. Some folders contain additional subfolders.
- Creation Date
- 2017 to 2018
- Date Issued
- 2019
- Authors
- Principal Investigator
- Co Principal Investigator
- Technical Details
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Gaussian 09, Revision D.01,M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2013.
- Funding
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This work was supported by the U.S. Department of Energy, Office of Science, Basic Energy Sciences, Catalysis Science Program, under Award No. DE-SC0009376. Thanks are due to the U.S. Department of Education for a GAANN fellowship (E.A.R.), and to the Alfred P. Sloan Foundation’s University Centre for Exemplary Mentoring (G.P.J.). This material is based upon work supported by the National Science Foundation Graduate Research Fellowship Program under Grant No. (DGE-1650112; G.P.J.). Any opinions, findings, and conclusions or recommendations expressed in this material are those of the author(s) and do not necessarily reflect the views of the National Science Foundation. We also acknowledge the Keck Foundation as well as the Extreme Science and Engineering Discovery Environment (XSEDE), which is supported by National Science Foundation grant number ACI-1548562 for provided computational resources.
- Topics
Format
View formats within this collection
- Language
- No linguistic content; Not applicable
- Identifier
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Identifier: Erik A Romero: https://orcid.org/0000-0002-5155-1684
Identifier: Glen P. Junor: https://orcid.org/0000-0002-6733-3577
Identifier: Guy Bertrand: https://orcid.org/0000-0003-2623-2363
Identifier: Rodolphe Jazzar: https://orcid.org/0000-0002-4156-7826
Identifier: Xi Chen: https://orcid.org/0000-0001-7086-5753
- Related Resources
- Junor, Glen P.; Romero, Erik A.; Chen, Xi; Jazzar, Rodolphe; Bertrand, Guy (2019). Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis. Angew. Chem. Int. Ed. https://doi.org/10.1002/anie.201814081
- Gaussian: http://gaussian.com/glossary/g09/
- Compound 14: CCDC 1883939 (Cambridge Crystallographic Data Centre): https://doi.org/10.5517/ccdc.csd.cc217d7y
- Compound 19: CCDC 1883940 (Cambridge Crystallographic Data Centre): https://doi.org/10.5517/ccdc.csd.cc217d8z
- Compound I^(Py): CCDC 1883941 (Cambridge Crystallographic Data Centre): https://doi.org/10.5517/ccdc.csd.cc217d90
Primary associated publication
Software
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- License
-
Creative Commons Attribution 4.0 International Public License
- Rights Holder
- UC Regents
- Copyright
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Under copyright (US)
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- Digital Object Made Available By
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Research Data Curation Program, UC San Diego, La Jolla, 92093-0175 (https://lib.ucsd.edu/rdcp)
- Last Modified
2023-06-06