Atropisomers of 6,6'-dinitro-2,2'-diphenic acid were first experimentally described case, by Christie and Kenner (1922).
Atropisomers are stereoisomers arising because of hindered rotation about a single bond, where energy differences due to steric strain or other contributors create a barrier to rotation that is high enough to allow for isolation of individual conformers.[1][2]
They occur naturally and are important in pharmaceutical design.[3] When the substituents are achiral, these conformers are enantiomers (atropoenantiomers), showing axial chirality; otherwise they are diastereomers (atropodiastereomers).[1]
^ abBringmann, Gerhard; Mortimer, Anne J. Price; Keller, Paul A.; Gresser, Mary J.; Garner, James; Breuning, Matthias (2005). "Atroposelective Synthesis of Axially Chiral Biaryl Compounds". Angewandte Chemie International Edition. 44 (34): 5384–5427. doi:10.1002/anie.200462661. PMID 16116589.
^Anslyn, Eric V.; Dougherty, Dennis A. (2006). Modern physical organic chemistry. Mill Valley, CA: University Science Books. ISBN 1-891389-31-9. OCLC 55600610.
^Clayden, Jonathan; Moran, Wesley J.; Edwards, Paul J.; LaPlante, Steven R. (2009). "The Challenge of Atropisomerism in Drug Discovery". Angew. Chem. Int. Ed. 48 (35): 6398–6401. doi:10.1002/anie.200901719. ISSN 1433-7851. PMID 19637174.
Atropisomers are stereoisomers arising because of hindered rotation about a single bond, where energy differences due to steric strain or other contributors...
1170-1171 ISBN 0-13-643669-2 "Atropisomer - an overview | ScienceDirect Topics". Metrano, Anthony J. (2018-06-09). "Atropisomers" (PDF). knowleslab.princeton...
rotation about the aryl–aryl bond is restricted so it results in chiral atropisomers, as in various ortho-substituted biphenyls, and in binaphthyls such as...
exist as optically active atropisomers. They both have antihistaminic and anti-inflammatory properties. However, the S-atropisomer of norketotifen (SN) causes...
interconversion of 1000 seconds or longer), the isomers are termed atropisomers (see: atropisomerism). The ring-flip of substituted cyclohexanes constitutes another...
Mabury SA, Muir DC (April 2002). "Enantiomer-specific accumulation of PCB atropisomers in the bowhead whale (Balaena mysticetus)". Environmental Science & Technology...
C-C bond between residues 5 and 7 by OxyC. The regioselectivity and atropisomer selectivity of these probable one-electron coupling reactions has been...
Torsional strain results from resistance to twisting about a bond. Atropisomerism An energetic form of axial chirality. This form of chirality derives...
\mathrm {BPC} )}}} This can be deduced from Spherical law of cosines Atropisomer "Angle Between Two Planes". TutorVista.com. Archived from the original...
be separated as stable compounds at room temperature, they are called atropisomers. Large molecules may have isomers that differ by the topology of their...
university in 1978, with the thesis titled "Asymmetric oxidation of phenols. Atropisomerism and optical activity". Following a short period at Shell in the Netherlands...
Theasinensin E is polyphenol flavonoid found in oolong tea. It's an atropisomer of theasinensin C. Yannai, Shmuel (2012). Dictionary of Food Compounds...
Theasinensin D is polyphenol flavonoid found in oolong tea. It's an atropisomer of theasinensin A. Yannai, Shmuel (2012). Dictionary of Food Compounds...
found in oolong tea. It is a deoxy derivative of theasinensin D and atropisomer of theasinensin F. Yannai, Shmuel (2012). Dictionary of Food Compounds...
stereogenic atom, but has axial chirality due to restricted rotation (atropisomerism). The barrier to racemization is high due to steric hindrance, which...
dehydrogenase enzymes. It is a yellow pigment. The structure exhibits atropisomerism, with the two enantiomers having different biochemical properties. Among...
Conformers which arise from single bond rotations, if not isolatable as atropisomers, do not count as distinct molecular configurations as the spatial connectivity...
sterically hindered. For this reason, some substituted biphenyls show atropisomerism; that is, the individual C2-symmetric-isomers are optically stable....
Cladosporium cladosporioides. Natural viriditoxin exists as a single atropisomer owing to restricted rotation about the C-C bond which joins the two naphthol...
Publishing. p. 80. ISBN 978-81-7648-743-6. Asymmetric oxidation of phenols. Atropisomerism and optical activity. Archived from the original on 6 January 2015....
restricted. Thus, both the (R)- and the (S)-enantiomers exist as atropisomers. Both atropisomers of (S)-metolachlor exhibit the same biological activity. Metolachlor...
created during fermentation, by oxidation of epigallocatechin gallate. Its atropisomer is theasinensin D. Theasinensin B Theasinensin C Theasinensin D Theasinensin...
orientalis (formerly designated Nocardia orientalis). Vancomycin exhibits atropisomerism—it has multiple chemically distinct rotamers owing to the rotational...
particularly where conformation has a role to play: asymmetric synthesis, atropisomerism, organolithium chemistry, remote stereochemical effects and dynamic...
pseudo-para dibromide. Thermal isomerisation then gives pseudo-ortho atropisomer of the dibromide. This isomer is subjected to lithium-halogen exchange...
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