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Rodrigues Silva D, de Azevedo Santos L, Hamlin TA, et al. Dipolar repulsion in α-halocarbonyl compounds revisited. Phys Chem Chem Phys. 2021;23(37):20883-20891doi: 10.1039/d1cp02502c.
Rodrigues Silva, D., de Azevedo Santos, L., Hamlin, T. A., Bickelhaupt, F. M., P Freitas, M., & Fonseca Guerra, C. (2021). Dipolar repulsion in α-halocarbonyl compounds revisited. Physical chemistry chemical physics : PCCP, 23(37), 20883-20891. https://doi.org/10.1039/d1cp02502c
Rodrigues Silva, Daniela, et al. "Dipolar repulsion in α-halocarbonyl compounds revisited." Physical chemistry chemical physics : PCCP vol. 23,37 (2021): 20883-20891. doi: https://doi.org/10.1039/d1cp02502c
Rodrigues Silva D, de Azevedo Santos L, Hamlin TA, Bickelhaupt FM, P Freitas M, Fonseca Guerra C. Dipolar repulsion in α-halocarbonyl compounds revisited. Phys Chem Chem Phys. 2021 Sep 29;23(37):20883-20891. doi: 10.1039/d1cp02502c. PMID: 34528039; PMCID: PMC8479779.
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Phys Chem Chem Phys. 2021 Sep 29;23(37):20883-20891. doi: 10.1039/d1cp02502c.

Dipolar repulsion in α-halocarbonyl compounds revisited.

Physical chemistry chemical physics : PCCP

Daniela Rodrigues Silva, Lucas de Azevedo Santos, Trevor A Hamlin, F Matthias Bickelhaupt, Matheus P Freitas, Célia Fonseca Guerra

Affiliations

  1. Department of Theoretical Chemistry, Amsterdam Institute of Molecular and Life Sciences (AIMMS), Amsterdam Center for Multiscale Modeling (ACMM), Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands. [email protected].
  2. Departamento de Química, Instituto de Ciências Naturais, Universidade Federal de Lavras, 37200-900, Lavras, MG, Brazil. [email protected].
  3. Institute for Molecules and Materials (IMM), Radboud University, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
  4. Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands.

PMID: 34528039 PMCID: PMC8479779 DOI: 10.1039/d1cp02502c

Abstract

The concept of dipolar repulsion has been widely used to explain several phenomena in organic chemistry, including the conformational preferences of carbonyl compounds. This model, in which atoms and bonds are viewed as point charges and dipole moment vectors, respectively, is however oversimplified. To provide a causal model rooted in quantitative molecular orbital theory, we have analyzed the rotational isomerism of haloacetaldehydes OHC-CH

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