Stereochemical Stability of Planar-Chiral Benzazepine Tricyclics: Inversion Energies of P- and S-Alkene Ligands
Jacqueline C. Calderón
1, 2
,
ALBERTO HERRERA
3
,
Alberto Diaz Herrera
3
,
Frank Heinemann
3
,
Jens Langer
4
,
Anthony Linden
5
,
Ahmed Chelouan
3
,
Alexander Grasruck
3
,
Rafael Añez
1
,
Timothy Clark
2
,
Romano Dorta
3
Publication type: Journal Article
Publication date: 2023-11-09
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
37944159
Organic Chemistry
Abstract
Inversion barriers ΔG‡ for planar chiral phosphine-alkene and sulfonamide-alkene hybrid ligands based on phenyl-dibenz[b,f]azepine have been determined by density-functional theory calculations. Analysis of the structural and electronic characteristics of the minima and transition states explains the magnitudes of ΔG‡ and the geometrical changes during the inversion process. The steric repulsion caused by bulky substituents attached to the azepine nitrogen atom has a pronounced effect on the ΔG‡ value, explaining, inter alia, the stereochemical stability of the P- and S-alkene ligands when compared to the fluxional parent compound where X = H.
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Calderón J. C. et al. Stereochemical Stability of Planar-Chiral Benzazepine Tricyclics: Inversion Energies of P- and S-Alkene Ligands // Journal of Organic Chemistry. 2023. Vol. 88. No. 23. pp. 16144-16154.
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Calderón J. C., HERRERA A., Herrera A. D., Heinemann F., Langer J., Linden A., Chelouan A., Grasruck A., Añez R., Clark T., Dorta R. Stereochemical Stability of Planar-Chiral Benzazepine Tricyclics: Inversion Energies of P- and S-Alkene Ligands // Journal of Organic Chemistry. 2023. Vol. 88. No. 23. pp. 16144-16154.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.3c01447
UR - https://pubs.acs.org/doi/10.1021/acs.joc.3c01447
TI - Stereochemical Stability of Planar-Chiral Benzazepine Tricyclics: Inversion Energies of P- and S-Alkene Ligands
T2 - Journal of Organic Chemistry
AU - Calderón, Jacqueline C.
AU - HERRERA, ALBERTO
AU - Herrera, Alberto Diaz
AU - Heinemann, Frank
AU - Langer, Jens
AU - Linden, Anthony
AU - Chelouan, Ahmed
AU - Grasruck, Alexander
AU - Añez, Rafael
AU - Clark, Timothy
AU - Dorta, Romano
PY - 2023
DA - 2023/11/09
PB - American Chemical Society (ACS)
SP - 16144-16154
IS - 23
VL - 88
PMID - 37944159
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2023_Calderón,
author = {Jacqueline C. Calderón and ALBERTO HERRERA and Alberto Diaz Herrera and Frank Heinemann and Jens Langer and Anthony Linden and Ahmed Chelouan and Alexander Grasruck and Rafael Añez and Timothy Clark and Romano Dorta},
title = {Stereochemical Stability of Planar-Chiral Benzazepine Tricyclics: Inversion Energies of P- and S-Alkene Ligands},
journal = {Journal of Organic Chemistry},
year = {2023},
volume = {88},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.3c01447},
number = {23},
pages = {16144--16154},
doi = {10.1021/acs.joc.3c01447}
}
Cite this
MLA
Copy
Calderón, Jacqueline C., et al. “Stereochemical Stability of Planar-Chiral Benzazepine Tricyclics: Inversion Energies of P- and S-Alkene Ligands.” Journal of Organic Chemistry, vol. 88, no. 23, Nov. 2023, pp. 16144-16154. https://pubs.acs.org/doi/10.1021/acs.joc.3c01447.
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