Electrostatic Effects on the Population of Atropisomers of Charged and Dipolar Derivatives of 1,8-Di(2‘-pyridyl)naphthalene
Dicationic 1‘,1‘-dimethyl (6a), dipolar 1‘,1‘-dioxide (6b), and 6‘,6‘-dipyridone (7) derivatives of 1,8-di(2‘-pyridyl)naphthalene were prepared. Proton NMR failed to reveal the presence of individual anti-syn atropisomers over a wide range of temperatures. By contrast, the 1‘,1‘‘-dimethyl derivative...
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| Published in | Journal of organic chemistry Vol. 62; no. 9; pp. 2763 - 2766 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
02.05.1997
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0022-3263 1520-6904 1520-6904 |
| DOI | 10.1021/jo962232f |
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| Abstract | Dicationic 1‘,1‘-dimethyl (6a), dipolar 1‘,1‘-dioxide (6b), and 6‘,6‘-dipyridone (7) derivatives of 1,8-di(2‘-pyridyl)naphthalene were prepared. Proton NMR failed to reveal the presence of individual anti-syn atropisomers over a wide range of temperatures. By contrast, the 1‘,1‘‘-dimethyl derivative of 1-(2‘-pyridyl)-8-(3‘‘-pyridyl)naphthalene (8), a positional isomer of 6a, existed in DMSO-d 6 as a 2:1 mixture of anti to syn atropisomers at ambient temperatures. Electrostatic repulsion is believed to cause the anti atropisomer to be favored, especially in 6a where the charged regions are closer together than in 8, owing to the splayed-out arrangement of the rings. AM1 and PM3 computations confirm that the anti is highly favored over the syn isomer for 6a, 6b, and 7. |
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| AbstractList | Dicationic 1',1'-dimethyl (6a), dipolar 1',1'-dioxide (6b), and 6',6'-dipyridone (7) derivatives of 1,8-di(2'-pyridyl)naphthalene were prepared. Proton NMR failed to reveal the presence of individual anti-syn atropisomers over a wide range of temperatures. By contrast, the 1',1"-dimethyl derivative of 1-(2'-pyridyl)-8-(3"-pyridyl)naphthalene (8), a positional isomer of 6a, existed in DMSO-d(6) as a 2:1 mixture of anti to syn atropisomers at ambient temperatures. Electrostatic repulsion is believed to cause the anti atropisomer to be favored, especially in 6a where the charged regions are closer together than in 8, owing to the splayed-out arrangement of the rings. AM1 and PM3 computations confirm that the anti is highly favored over the synisomer for 6a, 6b, and 7. Dicationic 1',1'-dimethyl (6a), dipolar 1',1'-dioxide (6b), and 6',6'-dipyridone (7) derivatives of 1,8-di(2'-pyridyl)naphthalene were prepared. Proton NMR failed to reveal the presence of individual anti-syn atropisomers over a wide range of temperatures. By contrast, the 1',1 ''-dimethyl derivative of 1-(2'-pyridyl)-8-(3 ''-pyridyl)naphthalen (8), a positional isomer of 6a, existed in DMSO-d(6) as a 2:1 mixture of anti to syn atropisomers at ambient temperatures. Electrostatic repulsion is believed to cause the anti atropisomer to be favored; especially in 6a where the charged regions are closer together than in 8, owing to the splayed-out arrangement of the rings. AM1 and PM3 computations confirm that the anti is highly favored over the syn isomer for 6a, 6b, and 7. Dicationic 1',1'-dimethyl (6a), dipolar 1',1'-dioxide (6b), and 6',6'-dipyridone (7) derivatives of 1,8-di(2'-pyridyl)naphthalene were prepared. Proton NMR failed to reveal the presence of individual anti-syn atropisomers over a wide range of temperatures. By contrast, the 1',1"-dimethyl derivative of 1-(2'-pyridyl)-8-(3"-pyridyl)naphthalene (8), a positional isomer of 6a, existed in DMSO-d(6) as a 2:1 mixture of anti to syn atropisomers at ambient temperatures. Electrostatic repulsion is believed to cause the anti atropisomer to be favored, especially in 6a where the charged regions are closer together than in 8, owing to the splayed-out arrangement of the rings. AM1 and PM3 computations confirm that the anti is highly favored over the synisomer for 6a, 6b, and 7.Dicationic 1',1'-dimethyl (6a), dipolar 1',1'-dioxide (6b), and 6',6'-dipyridone (7) derivatives of 1,8-di(2'-pyridyl)naphthalene were prepared. Proton NMR failed to reveal the presence of individual anti-syn atropisomers over a wide range of temperatures. By contrast, the 1',1"-dimethyl derivative of 1-(2'-pyridyl)-8-(3"-pyridyl)naphthalene (8), a positional isomer of 6a, existed in DMSO-d(6) as a 2:1 mixture of anti to syn atropisomers at ambient temperatures. Electrostatic repulsion is believed to cause the anti atropisomer to be favored, especially in 6a where the charged regions are closer together than in 8, owing to the splayed-out arrangement of the rings. AM1 and PM3 computations confirm that the anti is highly favored over the synisomer for 6a, 6b, and 7. Dicationic 1‘,1‘-dimethyl (6a), dipolar 1‘,1‘-dioxide (6b), and 6‘,6‘-dipyridone (7) derivatives of 1,8-di(2‘-pyridyl)naphthalene were prepared. Proton NMR failed to reveal the presence of individual anti-syn atropisomers over a wide range of temperatures. By contrast, the 1‘,1‘‘-dimethyl derivative of 1-(2‘-pyridyl)-8-(3‘‘-pyridyl)naphthalene (8), a positional isomer of 6a, existed in DMSO-d 6 as a 2:1 mixture of anti to syn atropisomers at ambient temperatures. Electrostatic repulsion is believed to cause the anti atropisomer to be favored, especially in 6a where the charged regions are closer together than in 8, owing to the splayed-out arrangement of the rings. AM1 and PM3 computations confirm that the anti is highly favored over the syn isomer for 6a, 6b, and 7. |
| Author | Maier, Nobert M Zoltewicz, John A Fabian, Walter M. F |
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| Keywords | OXIDATION DOMINANCE BENZENE MOLECULAR RECOGNITION 1,8-DIARYLNAPHTHALENES AROMATIC INTERACTIONS FERRICYANIDE ION POLAR/PI CATIONS |
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| Snippet | Dicationic 1‘,1‘-dimethyl (6a), dipolar 1‘,1‘-dioxide (6b), and 6‘,6‘-dipyridone (7) derivatives of 1,8-di(2‘-pyridyl)naphthalene were prepared. Proton NMR... Dicationic 1',1'-dimethyl (6a), dipolar 1',1'-dioxide (6b), and 6',6'-dipyridone (7) derivatives of 1,8-di(2'-pyridyl)naphthalene were prepared. Proton NMR... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Electrostatic Effects on the Population of Atropisomers of Charged and Dipolar Derivatives of 1,8-Di(2‘-pyridyl)naphthalene |
| URI | http://dx.doi.org/10.1021/jo962232f https://api.istex.fr/ark:/67375/TPS-GQSW81CT-X/fulltext.pdf http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=A1997WX15900016 https://www.ncbi.nlm.nih.gov/pubmed/11671637 https://www.proquest.com/docview/1859362376 |
| Volume | 62 |
| WOS | A1997WX15900016 |
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